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
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inquiryWith 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
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inquiryWITH 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
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inquiry1.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
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inquiryHello, 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
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inquiryHenan 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
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inquiryBest 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
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
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inquiryHunan 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
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inquiry1.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
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inquiryGOLDEN 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
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
Stock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai
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inquiryLower 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
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inquiryR & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou
Our clients, like BASF,CHEMO,Brenntag,ASR,Evonik,Merck and etc.Appearance:COA Storage:in stock Application:MSDS/TDS
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
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inquirySupply top quality products with a reasonable price Application:api
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
factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
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inquiryWe 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
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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
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inquiryhome-produced Application:medicine
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inquiryKnown 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
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inquiryfactory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
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.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
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inquiryPrice, 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
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inquiryBaiFuChem 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
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inquiry2-fluoro-6-methylaniline
1-fluoro-2-iodo-3-methylbenzene
Conditions | Yield |
---|---|
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
1-fluoro-2-iodo-3-methylbenzene
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 2h; Microwave irradiation; Inert atmosphere; Schlenk technique; | 70% |
benzimidazole
1-fluoro-2-iodo-3-methylbenzene
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 2h; Microwave irradiation; Inert atmosphere; Schlenk technique; | 48% |
1,2,4-Triazole
1-fluoro-2-iodo-3-methylbenzene
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide at 150℃; for 6h; Microwave irradiation; Inert atmosphere; Schlenk technique; | 31% |
1,2,3-Benzotriazole
1-fluoro-2-iodo-3-methylbenzene
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 5h; Sealed tube; Inert atmosphere; Schlenk technique; | 19% |
zinc(II) cyanide
1-fluoro-2-iodo-3-methylbenzene
2-fluoro-6-methyl-benzonitrile
Conditions | Yield |
---|---|
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
3-bromo-6-fluoro-2-methyl-benzonitrile
Conditions | Yield |
---|---|
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
3-ethenyl-6-fluoro-2-methylbenzonitrile
Conditions | Yield |
---|---|
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
6-fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile
Conditions | Yield |
---|---|
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
tert-butyl (3S)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
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
tert-butyl (3R,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
Conditions | Yield |
---|---|
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
tert-butyl (3S,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
Conditions | Yield |
---|---|
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
3-(2-bromo-acetyl)-6-fluoro-2-methyl-benzonitrile
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
tert-butyl (3R)-4-[2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxylethyl]-3-(hydroxymethyl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
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
A
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
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(3S)-benzyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
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
(7R,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate
Conditions | Yield |
---|---|
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
(7S,9aR)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino [1,2-a]pyrazine-2(6H)-carboxylate
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a ]pyrazine-2(6H)-carboxylate
Conditions | Yield |
---|---|
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
6-fluoro-2-methyl-3-[(3S,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile 2,2,2-trifluoroacetate
Conditions | Yield |
---|---|
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
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 | Yield |
---|---|
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
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 | Yield |
---|---|
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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