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Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

High quality 1-Fluoro-2-Iodo-3-Methylbenzene supplier in China

Cas:883502-14-5

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin

3-FLUORO-2-IODOTOLUENE

Cas:883502-14-5

Min.Order:1 Kilogram

FOB Price: $3.0 / 10.0

Type:Trading Company

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Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Top Purity CAS 883502-14-5 with fast shipping

Cas:883502-14-5

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

Benzene,1-fluoro-2-iodo-3-methyl- 883502-14-5

Cas:883502-14-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Benzene,1-fluoro-2-iodo-3-methyl-

Cas:883502-14-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Benzene,1-fluoro-2-iodo-3-methyl-

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Xiamen Hisunny Chemical Co.,Ltd

Best quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia

1-Fluoro-2-Iodo-3-Methylbenzene

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Manufacturers

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Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

3-Fluoro-2-iodotoluene

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Hunan chemfish Pharmaceutical co.,Ltd

Hunan chemfish Pharmaceutical co.,Ltd.located in Lugu High-tech industral park ,Hunan province . with its own R&D center and more than 10000㎡manufacture plant . Chemfish owns 40 reactors from 1000L to 8000L. With complete auxiliary equipment as

1-Fluoro-2-iodo-3-methylbenzene

Cas:883502-14-5

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

883502-14-5 CAS NO.883502-14-5

Cas:883502-14-5

Min.Order:1 Metric Ton

FOB Price: $7.0 / 8.0

Type:Trading Company

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Golden Pharma Co., Limited

GOLDEN PHARMA CO.,LIMITED.is a professional pharmaceutical company,our team have more than 20years expereince in pharmaceutical production and sales. we are a professional technical enterprise specializing in the R & D, production,QA regulation

2-Iodo-3-fluorotoluene

Cas:883502-14-5

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:as per your request Application:Used as Pharmaceutical Intermediates,ect. Transportation:as per your request

3-FLUORO-2-IODOTOLUENE

Cas:883502-14-5

Min.Order:10 Gram

Negotiable

Type:Trading Company

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Win-Win chemical Co.Ltd

Stock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai

3-Fluoro-2-Iodotoluene cas no. 883502-14-5 98%

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

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GIHI CHEMICALS CO.,LIMITED

Lower price, sample is available,SDS test documents are available,large stock in warehouseAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:Fine chemical intermediates, used as the main raw material for the synthe

1-Fluoro-2-iodo-3-methylbenzene

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Dingyan Chem Co., Ltd

R & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou

1-Fluoro-2-iodo-3-Methylbenzene

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Aecochem Corp.

Our clients, like BASF,CHEMO,Brenntag,ASR,Evonik,Merck and etc.Appearance:COA Storage:in stock Application:MSDS/TDS

1-Fluoro-2-Iodo-3-Methylbenzene

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Manufacturers

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Antimex Chemical Limied

Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali

3-Fluoro-2-iodotoluene

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Changchun Artel lmport and Export trade company

Supply top quality products with a reasonable price Application:api

883502-14-5

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Trading Company

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Hangzhou Fandachem Co.,Ltd

3-FLUORO-2-IODOTOLUENEAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air, by sea, by express

3-FLUORO-2-IODOTOLUENE

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Other

inquiry

Henan Kanbei Chemical Co.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

3-FLUORO-2-IODOTOLUENE

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

HANGZHOU TIANYE CHEMICALS CO., LTD.

We product this chemical more than 10 years . We are very experience to export it to many countries, Our superior & stable quality , competitive price gain warm reception from our customers. Application:Pharm intermediate

2-BroMo-5-fluoro-4-nitroaniline

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Shanghai Chinqesen Biotechnology Co., Ltd.

Good Quality Package:1kg/bag Application:Medical or chemical Transportation:Air/Train/Sea Port:Shenzhen

883502-14-5

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Hunan Russell Chemicals Technology Co.,Ltd

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:Foil bag; Drum; Plastic bottle Application:Pharma;Industry;Agricultural Transportation:by sea or air Port:any port in China

1-Fluoro-2-iodo-3-methylbenzene 883502-14-5

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Zibo Hangyu Biotechnology Development Co., Ltd

home-produced Application:medicine

3-FLUORO-2-IODOTOLUENE

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Yuanye Bio-Technology Co., Ltd.

Known for its best quality and competitve price, this chemicals we offered is widely appreciated by our customers.Appearance:White powder Storage:keep sealed and keep from direct light Package:According client's requirements Application:pharmaceutica

3-Fluoro-2-Iodotoluene manufacturer

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

ZHEJIANG JIUZHOU CHEM CO.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

3-FLUORO-2-IODOTOLUENE

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Bide Pharmatech Ltd

Our mission is to provide high-quality and innovative products to our customers. By offering a broad range of products, custom synthesis and personalized services, Bide can help scientists speeding up their research in the chemical and pharmaceutical

1-Fluoro-2-iodo-3-methylbenzene

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Other

inquiry

Amadis Chemical Co., Ltd.

1.Professional synthesis laboratory and production base. 2.Strong synthesis team and service team. 3.Professional data management system. 4.We provide the professional test date and product information ,ex. HNMR ,CNMR,FNMR, HPLC/G

1-Fluoro-2-iodo-3-methyl-benzene

Cas:883502-14-5

Min.Order:10 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Jilin haofei import and export trade Co.,Ltd

Price, service, company and transport advantage: 1. Best service, place of origin China, high quality, and reasonable price. 2. It's customers' right to choose the package (EMS, DHL, FEDEX, UPS). 3. It's customers' right

Best price/ 3-Fluoro-2-iodotoluene CAS NO.883502-14-5

Cas:883502-14-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Xiamen BaiFuchem Co.,Ltd

BaiFuChem is a Professional chemical raw material supplier in China, our main products include Biochemical , Pharma Intermediate and Organic chemical etc. BaiFuChem have wealth of products,experience , expertise and state-of-the-art

High purity 1-Fluoro-2-Iodo-3-Methylbenzene

Cas:883502-14-5

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

Synthetic route

2-fluoro-6-methylaniline
443-89-0

2-fluoro-6-methylaniline

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

Conditions
ConditionsYield
Stage #1: 2-fluoro-6-methylaniline With hydrogenchloride In water at 0℃; for 0.25h;
Stage #2: With sodium nitrite In water at 0℃; for 1.67h;
Stage #3: With potassium iodide In water at 0℃; for 2.17h;
73%
NH-pyrazole
288-13-1

NH-pyrazole

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

1-(2-iodo-3-methylphenyl)-1H-pyrazole

1-(2-iodo-3-methylphenyl)-1H-pyrazole

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 2h; Microwave irradiation; Inert atmosphere; Schlenk technique;70%
benzimidazole
271-44-3

benzimidazole

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

1-(2-iodo-3-methylphenyl)-1H-indazole

1-(2-iodo-3-methylphenyl)-1H-indazole

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 2h; Microwave irradiation; Inert atmosphere; Schlenk technique;48%
1,2,4-Triazole
288-88-0

1,2,4-Triazole

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

1-(2-iodo-3-methylphenyl)-1H-1,2,4-triazole

1-(2-iodo-3-methylphenyl)-1H-1,2,4-triazole

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 6h; Microwave irradiation; Inert atmosphere; Schlenk technique;31%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

1-(2-iodo-3-methylphenyl)-1H-benzo[d][1,2,3]triazole

1-(2-iodo-3-methylphenyl)-1H-benzo[d][1,2,3]triazole

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 5h; Sealed tube; Inert atmosphere; Schlenk technique;19%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

2-fluoro-6-methyl-benzonitrile
198633-76-0

2-fluoro-6-methyl-benzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide at 80℃; for 16h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide at 80℃; for 16h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0) In dimethyl amine at 80℃; Inert atmosphere;
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

3-bromo-6-fluoro-2-methyl-benzonitrile
1255207-47-6

3-bromo-6-fluoro-2-methyl-benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

3-ethenyl-6-fluoro-2-methylbenzonitrile
1255207-48-7

3-ethenyl-6-fluoro-2-methylbenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

6-fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile
1255207-46-5

6-fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

tert-butyl (3S)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate
1426071-25-1

tert-butyl (3S)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
View Scheme
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
View Scheme
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

tert-butyl (3R,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
1426072-82-3

tert-butyl (3R,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 16 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
8: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

tert-butyl (3S,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
1426071-26-2

tert-butyl (3S,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 16 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
8: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

3-(2-bromo-acetyl)-6-fluoro-2-methyl-benzonitrile
1426073-08-6

3-(2-bromo-acetyl)-6-fluoro-2-methyl-benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 20 - 100 °C
3.2: 0.75 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: bis(triphenylphosphine)palladium(II) dichloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.75 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide; trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

C12H12FNO

C12H12FNO

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3R,9aS)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-3-hydroxy-hexahydro-pyrazino[2,1-c][ 1,4]oxazine-8-carboxylic acid tert-butyl ester
1426073-09-7

(3R,9aS)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-3-hydroxy-hexahydro-pyrazino[2,1-c][ 1,4]oxazine-8-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
4.1: diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
4.1: diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(S)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-6,7,9,9a-tetrahydro-1H-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester
1426073-10-0

(S)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-6,7,9,9a-tetrahydro-1H-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
4.1: diisopropylamine / tetrahydrofuran / 18 h / 20 °C
5.1: triethylamine / dichloromethane / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.5 h / 0 - 5 °C
4.1: diisopropylamine / tetrahydrofuran / 18 h / 20 °C
5.1: triethylamine / dichloromethane / 0.5 h / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

C21H28FN3O6S

C21H28FN3O6S

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

tert-butyl (3R)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxylethyl]-3-(hydroxymethyl)piperazine-1-carboxylate
1426071-27-3

tert-butyl (3R)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxylethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 1 h / 150 °C / Microwave irradiation
View Scheme
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5: ethanol / 1 h / 150 °C / Microwave irradiation
View Scheme
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 1 h / 150 °C / Microwave irradiation
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

A

tert-butyl (3S,9aR)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
1426072-83-4

tert-butyl (3S,9aR)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

B

tert-butyl (3R,9aR)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
1426072-84-5

tert-butyl (3R,9aR)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 12 h / 20 °C
6.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 1 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 100 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3S,9aR)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-3-hydroxy-hexahydro-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester
1426073-11-1

(3S,9aR)-3-(3-cyano-4-fluoro-2-methyl-phenyl)-3-hydroxy-hexahydro-pyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: bis(triphenylphosphine)palladium(II) dichloride / 1,4-dioxane / 22 h / 100 °C
3.2: 0.75 h / 0 - 5 °C
4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide; trifluorormethanesulfonic acid / 1 h / 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5: 18 h / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3S)-benzyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate
1426071-28-4

(3S)-benzyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(7R,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate
1426072-85-6

(7R,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / toluene / 100 - 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(7S,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate
1426072-86-7

(7S,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / toluene / 100 - 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3R,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8-(9H,9aH)-dicarboxylate
1426071-29-5

(3R,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8-(9H,9aH)-dicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino [1,2-a]pyrazine-2(6H)-carboxylate
1426071-30-8

(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino [1,2-a]pyrazine-2(6H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3S,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8 (9H,9aH)-dicarboxylate
1426071-31-9

(3S,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8 (9H,9aH)-dicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / toluene / 100 - 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid / dichloromethane / 4 h / 35 °C
8.2: 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide; trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 34 °C
8.2: 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a ]pyrazine-2(6H)-carboxylate
1426071-32-0

(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a ]pyrazine-2(6H)-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / dimethyl amine / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: sulfuryl dichloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / 16 h / 80 °C / Inert atmosphere
2.1: sulfuric acid; N-Bromosuccinimide / 3 h / 0 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / toluene / 100 - 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: chlorosulphone / 1 h / 90 °C
7.2: 1 h / 0 - 90 °C / Sealed tube
8.1: tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid / dichloromethane / 4 h / 35 °C
8.2: 20 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: N-Bromosuccinimide; trifluorormethanesulfonic acid / 1 h / 20 °C
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 20 °C
5.1: ethanol / 0.5 h / 150 °C / Microwave irradiation
6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6.2: 1 h / 0 °C
7.1: thionyl chloride / 1 h / 90 °C
7.2: 1 h / 90 °C / Sealed tube
8.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 34 °C
8.2: 20 °C
9.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

6-fluoro-2-methyl-3-[(3S,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile 2,2,2-trifluoroacetate
1426072-49-2

6-fluoro-2-methyl-3-[(3S,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile 2,2,2-trifluoroacetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
7.1: 1 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
7.1: 1 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Inert atmosphere; Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 16 h / 100 °C / Inert atmosphere
7: 1 h / 20 °C
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

3-((3S,9aS)-8-(2-(5-(1H-tetrazol-1-yl)pyridin-2-yl)acetyl)octahydropyrazino[2,1-c][1,4]oxazin-3-yl)-6-fluoro-2-methylbenzonitrile
1443735-03-2

3-((3S,9aS)-8-(2-(5-(1H-tetrazol-1-yl)pyridin-2-yl)acetyl)octahydropyrazino[2,1-c][1,4]oxazin-3-yl)-6-fluoro-2-methylbenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: triethylamine
7.1: ethyl acetate; hexane / 50 °C
8.1: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
9.1: 1 h / 20 °C
10.1: triethylamine / dichloromethane / 0.08 h
10.2: 2 h
View Scheme
Multi-step reaction with 10 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: triethylamine
7.1: ethyl acetate; hexane / 50 °C
8.1: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
9.1: 1 h / 20 °C
10.1: triethylamine / dichloromethane / 0.08 h
10.2: 2 h
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
7.1: 1 h / 20 °C
8.1: triethylamine / dichloromethane / 0.08 h
8.2: 2 h
View Scheme
1-fluoro-2-iodo-3-methylbenzene
883502-14-5

1-fluoro-2-iodo-3-methylbenzene

6-fluoro-2-methyl-3-[(3S,9aS)-8-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile
1443735-04-3

6-fluoro-2-methyl-3-[(3S,9aS)-8-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
8: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
9: 1 h / 20 °C
10: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 4 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6: triethylamine
7: ethyl acetate; hexane / 50 °C
8: hydrogen; 5% Pd-CaCO3 / methanol / 38 h / 40 °C / Inert atmosphere
9: 1 h / 20 °C
10: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 4 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2.1: trifluorormethanesulfonic acid; N-Bromosuccinimide / 1 h / 0 - 20 °C
3.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 100 °C
4.1: N-Bromosuccinimide; water / tetrahydrofuran; 1,4-dioxane / 0.5 h / 0 - 5 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 20 °C
6.2: 2 h / 20 °C
7.1: 1 h / 20 °C
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 4 h / 20 °C
View Scheme

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