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Senova Pharma

Multi-target purpose intermediate with wide usage Commercial production from grams to tons, with technical documents package support, and audit and inspection support. With high purity and optimized and stable process. Self Innovation Appeara

Crizotinib intermediate

Cas:877399-74-1

Min.Order:10 Gram

Negotiable

Type:Manufacturers

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe

Hangzhou Think Chemical Co. Ltd

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate CAS No.:877399-74-1 Name: tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new api, intermedi

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:1 Kilogram

FOB Price: $5.0

Type:Manufacturers

inquiry

ANQING CHICO PHARMACEUTICAL CO.,LTD.

High quality. Factory supply. In stock. Best price.1.Quick response within 24 hours;2.Best quality in your requirement;?3.We pay more attention on delivery time, and usually ship on time;4.Under the premise of safety and effectiveness, we can produce

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

tert-Butyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]-piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Jinan Finer Chemical Co., Ltd

Product Description Product website: http://www.finerchem.com/pro01en/id/967.html Product Name tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidi

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:1 Gram

FOB Price: $66.0

Type:Lab/Research institutions

inquiry

Henan Tianfu Chemical Co., Ltd.

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate Basic information Product Name: tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-

877399-74-1

Cas:877399-74-1

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:1 Kilogram

FOB Price: $2.0 / 10.0

Type:Trading Company

inquiry

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

Factory direct supply CAS 877399-74-1 with best quality

Cas:877399-74-1

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Hubei Langyou International Trading Co., Ltd

1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta

High quality CAS877399-74-1 InterMediate Ⅱ of Crizotinib with best price

Cas:877399-74-1

Min.Order:10 Gram

Negotiable

Type:Other

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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

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has built platforms for the research, development and manufac

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:1 Gram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Shijiazhuang Sdyano Fine Chemical Co., Ltd

1. Best prices with satisfied quality; 2. It's clients' right to choose the package's Courier (EMS, DHL, FedEx, UPS); 3.It's clients' right to choose the packing way for his produccts from many recent effective packing ways;

Qingdao Beluga Import and Export Co., LTD

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate CAS:877399-74-1 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, pro

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

LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&amp

Wuhan Wonda Pharm Limited

1.high quality: quality is life. quality is the most important element for all goods. we have a lab doing research in wuhan china. hplc and nmr is available if needed. 2.reasonable price: we provide high quality products wi

High Purity Crizotinib intermediates

Cas:877399-74-1

Min.Order:10 Gram

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

CAS NO.:877399-74-1

Cas:877399-74-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

HANWAYS CHEMPHARM CO.,LIMITED

We are concentrating on the R&D and technical service of APIs and pharmaceutical intermediates Application:Pharmaceutical intermediate Port:Chinese main port

Crizotinib intermediates

Cas:877399-74-1

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Triumph International Development Limilted

Appearance:Off-white to white solid powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for Synthesis API and Research Transportation:By Sea/Air/Courier Port:

Crizotinib intermediates|877399-74-1

Cas:877399-74-1

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Hope Chem Co., Ltd

1. Product advantages: exquisite appearance and unique functions. 2. Product Advantages: Our products are the best,fast speed ,in large stock 3. High-quality products and thoughtful service are your greatest satisfaction. 4. The product

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hubei Lidu New Material Technology Co., Ltd

Hubei Lidu New Materials Technology Co. , Ltd. is located in No. 12,3C Industrial Park, Zhongxiang Economic Development Zone, Hubei Province. The company is committed to fine chemical raw materials, pharmaceutical intermediates and other production,

Tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

tert-butyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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

Chemlyte Solutions

Chemlyte Solutions believe that customers and suppliers deserve much more than what traditional distributors can offer. To grow in today s fast-paced and increasingly competitive market it is essential to be able to quickly adapt to market forces eff

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

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

Hangzhou Lingrui Chemical Co.,Ltd.

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylateAppearance:powder Storage:store in a cool dry place and keep away from strong Package:according to customers' requirements Application:in research T

HANGZHOU YUNUO CHEMICAL CO.,LTD

moderate price & quick delivery Appearance:powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:100g/bottle,1kg/bottle,25kg/drum or as per your request Application:Used as Pharmaceutical Intermediates Transp

4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Cas:877399-74-1

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Synthetic route

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
877399-50-3

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With C54H44NO2PPdS; potassium acetate In tetrahydrofuran at 80℃; for 24h; Miyaura Borylation Reaction; Inert atmosphere; Sealed tube;94%
With isopropylmagnesium chloride In tetrahydrofuran at -10 - 30℃; for 9h; Inert atmosphere; Large scale;81%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 0.166667h; Inert atmosphere;44%
tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-73-0

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere;87.9%
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere;87.9%
With potassium acetate; tetrakis(triphenylphosphine) palladium(0) In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere;83%
tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-73-0

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1195-66-0

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -10 - 0℃; for 5.25h; Large scale reaction;
Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 25℃; for 10.75h; Large scale reaction;
81%
Stage #1: tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -10 - 20℃; for 2h; Inert atmosphere;
Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
61.5%
With isopropylmagnesium chloride In tetrahydrofuran at 0 - 30℃;
In tetrahydrofuran
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
877399-50-3

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1195-66-0

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 20 - 30℃; for 12h;
Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 30℃; for 6h;
80%
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
877399-50-3

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
185990-03-8

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 1h;61%
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
877399-50-3

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 20 - 30℃; for 12h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 30℃; for 6h;
60%
With n-butyllithium In tetrahydrofuran; hexane at -70 - 20℃; for 3h;51%
pyrazole-4-boronic acid pinacol ester
269410-08-4

pyrazole-4-boronic acid pinacol ester

1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate
141699-59-4

1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 18h;48%
With caesium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere;44%
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;39%
1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate
141699-59-4

1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: pyrazole-4-boronic acid pinacol ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate In N,N-dimethyl-formamide at 100℃;
29%
Multi-step reaction with 2 steps
1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 110 °C / Inert atmosphere; Microwave irradiation
2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 4 °C / Inert atmosphere
1.2: 12 h / 100 °C / Inert atmosphere
2.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere
View Scheme
pyrazole-4-boronic acid pinacol ester
269410-08-4

pyrazole-4-boronic acid pinacol ester

tert-butyl 4-bromo-1-piperidinecarboxylate
180695-79-8

tert-butyl 4-bromo-1-piperidinecarboxylate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl acetamide at 85℃; for 12h; Inert atmosphere;5%
t-butyl 4-hydroxy piperidine-1-carboxylate
109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 110 °C / Inert atmosphere; Microwave irradiation
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 4 °C / Inert atmosphere
2.2: 12 h / 100 °C / Inert atmosphere
3.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / tert-butyl methyl ether / 1 h / -5 - 22 °C / Inert atmosphere
2.1: caesium carbonate / n-methyl-2-pyrrilidone / 18.5 h / 80 °C
3.1: isopropylmagnesium chloride / tetrahydrofuran / 5.25 h / -10 - 0 °C / Large scale reaction
3.2: 10.75 h / 20 - 25 °C / Large scale reaction
View Scheme
4-HYDROXYPIPERIDINE
5382-16-1

4-HYDROXYPIPERIDINE

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
3: sodium hydride / N,N-dimethyl-formamide / 12 h / 80 °C
4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: triethylamine
2: triethylamine; dmap / dichloromethane
3: sodium hydride / N,N-dimethyl-formamide
4: tetrahydrofuran
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 80 °C
4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere; Sealed tube
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
3: sodium hydride / N,N-dimethyl-formamide / 12 h / 80 °C
4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 80 °C
4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere; Sealed tube
View Scheme
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 21 h / 80 °C / Inert atmosphere; Glovebox
2: caesium carbonate / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
View Scheme
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

2-chloromalonaldehyde
36437-19-1

2-chloromalonaldehyde

tert-butyl 4-hydrazino-piperidine-1-carboxylate
1196486-69-7

tert-butyl 4-hydrazino-piperidine-1-carboxylate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2-chloromalonaldehyde; tert-butyl 4-hydrazino-piperidine-1-carboxylate With boron trifluoride diethyl etherate In toluene Reflux; Inert atmosphere;
Stage #2: tetrahydroxydiboron With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 80℃; for 4h; Inert atmosphere;
Stage #3: 2,3-dimethyl-2,3-butane diol Inert atmosphere;
10.1 g
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

2-Bromo-malonaldehyde
2065-75-0

2-Bromo-malonaldehyde

tert-butyl 4-hydrazino-piperidine-1-carboxylate
1196486-69-7

tert-butyl 4-hydrazino-piperidine-1-carboxylate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 2-Bromo-malonaldehyde; tert-butyl 4-hydrazino-piperidine-1-carboxylate With boron trifluoride diethyl etherate In toluene Reflux; Inert atmosphere;
Stage #2: tetrahydroxydiboron With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 20℃; for 12h; Inert atmosphere;
Stage #3: 2,3-dimethyl-2,3-butane diol Inert atmosphere;
8.8 g
N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrazine hydrate / ethanol / 0.5 h / 20 °C
1.2: 2 h / 20 °C
2.1: boron trifluoride diethyl etherate / toluene / Reflux; Inert atmosphere
2.2: 12 h / 20 °C / Inert atmosphere
2.3: Inert atmosphere
View Scheme
tert-butyl chloroformate
24608-52-4

tert-butyl chloroformate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine
2: triethylamine; dmap / dichloromethane
3: sodium hydride / N,N-dimethyl-formamide
4: tetrahydrofuran
View Scheme
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-73-0

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -25 - 20℃; for 2h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran at 5 - 10℃; for 2.5h;
Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran at 60℃; for 2.5h; Temperature; Concentration;
pyrazole-4-boronic acid pinacol ester
269410-08-4

pyrazole-4-boronic acid pinacol ester

N-Boc-piperidine-4-yl halide

N-Boc-piperidine-4-yl halide

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine hydrochloride
1175273-62-7

4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 35℃; for 3h;100%
Stage #1: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate With trifluoroacetic acid at 0 - 20℃; for 0.166667h;
Stage #2: With hydrogenchloride In 1,4-dioxane
100%
With hydrogenchloride In 1,4-dioxane at 35℃; for 3h;
With hydrogenchloride In ethyl acetate at 20℃; for 2h;
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine hydrochloride

4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; ethyl acetate at 20℃;100%
With hydrogenchloride In 1,4-dioxane at 20℃; for 1h;100%
With hydrogenchloride In 1,4-dioxane at 20℃; for 16h;
With hydrogenchloride In 1,4-dioxane at 35℃; for 3h;
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(S)-methyl 6-bromo-2-methyl-5-propoxy-3,4-dihydroquinoline-1(2H)-carboxylate

(S)-methyl 6-bromo-2-methyl-5-propoxy-3,4-dihydroquinoline-1(2H)-carboxylate

(S)-methyl 6-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1H-pyrazol-4-yl)-2-methyl-5-propoxy-3,4-dihydroquinoline-1(2H)-carboxylate

(S)-methyl 6-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1H-pyrazol-4-yl)-2-methyl-5-propoxy-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions
ConditionsYield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate In 1,4-dioxane; water at 100℃; for 5h; Microwave irradiation;100%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazol-1-yl)piperidine
1175708-03-8

4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazol-1-yl)piperidine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 4h;100%
With trifluoroacetic acid In dichloromethane at 20 - 40℃; for 0.25h;100%
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

6-bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine

6-bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine

tert-butyl 4-(4-(3-chloro-4-methoxypyrazolo[1,5-a]pyridin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(3-chloro-4-methoxypyrazolo[1,5-a]pyridin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; Sealed tube;100%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

3-chloro-N-(3,5-dimethoxyphenyl)quinoxalin-6-amine
1346245-13-3

3-chloro-N-(3,5-dimethoxyphenyl)quinoxalin-6-amine

tert-butyl 4-(4-(7-((3,5-dimethoxyphenyl)amino)quinoxalin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(7-((3,5-dimethoxyphenyl)amino)quinoxalin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere;99%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(S)-2-((4-(5-bromopyrimidine-2-yl)morpholin-2-yl)methyl)-6-(3-fluorophenyl)pyridazine-3(2H)-one

(S)-2-((4-(5-bromopyrimidine-2-yl)morpholin-2-yl)methyl)-6-(3-fluorophenyl)pyridazine-3(2H)-one

(S)-tert-butyl 4-(4-(2-(2-((3-(3-fluorophenyl)-6-oxopyridazin-1(6H)-yl)methyl)morpholino)pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(S)-tert-butyl 4-(4-(2-(2-((3-(3-fluorophenyl)-6-oxopyridazin-1(6H)-yl)methyl)morpholino)pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere;98%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran at 80℃; for 2h; Inert atmosphere;86 mg
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

6-bromo-4-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

6-bromo-4-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

tert-butyl 4-(4-(3-cyano-4-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(3-cyano-4-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 80℃; Inert atmosphere; Sealed tube;98%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

5-bromo-3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine
1450642-85-9

5-bromo-3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
1562305-29-6

tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 20℃; for 15h;96%
5-amino-2-bromopyrazine
59489-71-3

5-amino-2-bromopyrazine

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(5-aminopyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(5-aminopyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; Suzuki Coupling; Inert atmosphere; Sealed tube;96%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

5-bromo-2-methyl-3-nitropyridine
911434-05-4

5-bromo-2-methyl-3-nitropyridine

tert-butyl 4-[4-(6-methyl-5-nitropyridin-3-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate
1229457-95-7

tert-butyl 4-[4-(6-methyl-5-nitropyridin-3-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methyl-3-nitropyridine; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 20℃; for 0.333333h;
Stage #2: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate With potassium carbonate In 1,2-dimethoxyethane; isopropyl alcohol at 20 - 85℃;
95%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine
1569895-70-0

(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine

C31H38Cl2FN5O5
1569895-72-2

C31H38Cl2FN5O5

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere;95%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 3h; Suzuki Coupling;85%
5-bromo-3-[1 (R)-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine

5-bromo-3-[1 (R)-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

4-(4-{6-amino-5-[(R)-1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

4-(4-{6-amino-5-[(R)-1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,2-dimethoxyethane; water at 90℃; for 3h; Suzuki coupling; Inert atmosphere;94%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide for 16h; Inert atmosphere;80%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; caesium carbonate In water; benzene at 70℃; for 5h; Inert atmosphere;76%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

7-bromo-6-methylimidazo[1,2-a]pyridine

7-bromo-6-methylimidazo[1,2-a]pyridine

tert-butyl 4-(4-(6-methylimidazo[1,2-a]pyridin-7-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(6-methylimidazo[1,2-a]pyridin-7-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 50℃; for 1.5h;93%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine

5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine

tert-butyl 4-(4-(6-((tert-butoxycarbonyl)amino)-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(6-((tert-butoxycarbonyl)amino)-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere;92.3%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

5-bromo-1H-pyrrolo[2,3-b]pyridine
183208-35-7

5-bromo-1H-pyrrolo[2,3-b]pyridine

4-(4-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
1562305-10-5

4-(4-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 2h; Suzuki-Miyaura Coupling;92%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water Inert atmosphere; Reflux;71%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water Inert atmosphere; Reflux;71%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 20℃; for 15h;46.2%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere;
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-benzyloxycarbonylaminopyridine

5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-benzyloxycarbonylaminopyridine

tert-butyl 4-(4-(6-(((benzyloxy)carbonyl)amino)-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(6-(((benzyloxy)carbonyl)amino)-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere;91.8%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

C13H10BrN3O
1239369-33-5

C13H10BrN3O

C26H30N6O3
1239369-35-7

C26H30N6O3

Conditions
ConditionsYield
Stage #1: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate; C13H10BrN3O With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 20℃; for 0.5h; Suzuki coupling;
Stage #2: With sodium carbonate In 1,4-dioxane; water for 3h; Suzuki coupling; Reflux;
91%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

methyl 6-((6-bromo-2-oxobenzo[d]thiazole-3(2H)-yl)methyl)nicotinate

methyl 6-((6-bromo-2-oxobenzo[d]thiazole-3(2H)-yl)methyl)nicotinate

methyl 6-((6-(1-(1-(tert-butoxycarbonyl)piperidine-4-yl)-1H-pyrazole-4-yl)-2-oxobenzo[d]thiazole-3(2H)-yl)methyl)nicotinate

methyl 6-((6-(1-(1-(tert-butoxycarbonyl)piperidine-4-yl)-1H-pyrazole-4-yl)-2-oxobenzo[d]thiazole-3(2H)-yl)methyl)nicotinate

Conditions
ConditionsYield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); caesium carbonate In 1,4-dioxane; water at 100℃; for 18h;90.7%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

1-((1-(5-bromopyrimidin-2-yl)piperidin-3-yl)methyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1 , 2,3]triazolo[4,5-b]pyrazine

1-((1-(5-bromopyrimidin-2-yl)piperidin-3-yl)methyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1 , 2,3]triazolo[4,5-b]pyrazine

tert-butyl 4-(4-(2-(3-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidin-1-yl)pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(2-(3-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidin-1-yl)pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere;90%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 80℃; for 12h;90%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

N-(3-(2-(3-amino-6-bromopyrazin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)acetamide

N-(3-(2-(3-amino-6-bromopyrazin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)acetamide

tert-butyl 4-(4-(6-(1-(3-acetamidophenyl)-1H-benzo[d]imidazol-2-yl)-5-aminopyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(6-(1-(3-acetamidophenyl)-1H-benzo[d]imidazol-2-yl)-5-aminopyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;90%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

3-hydroxy-5-bromo-2-nitropyridine
691872-15-8

3-hydroxy-5-bromo-2-nitropyridine

C18H23N5O5

C18H23N5O5

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 16h; Inert atmosphere; Large scale;90%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(R)-5-bromo-N,N-bis-(tert-butoxycarbonyl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine-2-amine
877399-47-8

(R)-5-bromo-N,N-bis-(tert-butoxycarbonyl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine-2-amine

C36H46Cl2FN5O7

C36H46Cl2FN5O7

Conditions
ConditionsYield
With 5%-palladium/activated carbon; potassium carbonate In water; toluene at 70℃; for 4h; Temperature; Reagent/catalyst; Suzuki Coupling; Inert atmosphere;90%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(S)-4-(2-chloro-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-yl)-3-phenylmorpholine

(S)-4-(2-chloro-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-yl)-3-phenylmorpholine

tert-butyl (S)-4-(4-(6-(3,5-dimethylisoxazol-4-yl)-4-(3-phenylmorpholino)quinazolin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl (S)-4-(4-(6-(3,5-dimethylisoxazol-4-yl)-4-(3-phenylmorpholino)quinazolin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 90℃; for 1.5h; Inert atmosphere;87%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(5-bromo-3-(2-methoxybenzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl pivalate

(5-bromo-3-(2-methoxybenzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl pivalate

tert-butyl 4-(4-(3-(2-methoxybenzoyl)-1-(pivaloyloxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(3-(2-methoxybenzoyl)-1-(pivaloyloxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 1.5h; Suzuki-Miyaura Coupling;86%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(R)-2-bromo-7-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)quinoxaline

(R)-2-bromo-7-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)quinoxaline

tert-butyl (R)-4-(4-(7-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)quinoxalin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl (R)-4-(4-(7-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)quinoxalin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; caesium carbonate In water; toluene at 80℃; for 5h; Inert atmosphere;86%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(5-bromo-3-(2-chloro-4-(phenoxymethyl)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl pivalate

(5-bromo-3-(2-chloro-4-(phenoxymethyl)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl pivalate

tert-butyl 4-(4-(3-(2-chloro-4-(phenoxymethyl)benzoyl)-1-((pivaloyloxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-(3-(2-chloro-4-(phenoxymethyl)benzoyl)-1-((pivaloyloxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 1.5h; Suzuki-Miyaura Coupling;85%
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

1-[(2S)-6-bromo-5-(2-fluorophenoxy)-2-methyl-1,2,3,4-tetrahydroquinolin-1-yl]ethan-1-one

1-[(2S)-6-bromo-5-(2-fluorophenoxy)-2-methyl-1,2,3,4-tetrahydroquinolin-1-yl]ethan-1-one

(S)-tert-butyl 4-(4-(1-acetyl-5-(2-fluorophenoxy)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

(S)-tert-butyl 4-(4-(1-acetyl-5-(2-fluorophenoxy)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 12h;85%

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