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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.Free samples will be provided. 5.Ensure specifications an

Axitinib

Cas:319460-85-0

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's 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. DayangChem can provide different quantities

Axitinib Manufacturer/High quality/Best price/In stock

Cas:319460-85-0

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Hangzhou Dingyan Chem Co., Ltd

Items Standard Result Description Almost white powder Complies Identification H-NMR, MS,HPLC

High purity Various Specifications Axitinib CAS:319460-85-0

Cas:319460-85-0

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Manufacturers

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GIHI CHEMICALS CO.,LIMITED

GIHI CHEMICALS exported this product to many countries and regions at best price. if you are looking for the material's manufacturer or supplier in china, GIHI CHEMICALS is your best choice. pls contact with us freely for getting detailed prod

319460-85-0 Axitinib price

Cas:319460-85-0

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Lab/Research institutions

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Simagchem Corporation

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

High quality Axitinib supplier in China

Cas:319460-85-0

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

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Wuhan Fortuna Chemical Co.,Ltd

Axitinib CAS 319460-85-0 Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical & its intermediates, Food/Feed additives, Fine chemicals in distributing th

Axitinib CAS 319460-85-0

Cas:319460-85-0

Min.Order:1 Kilogram

FOB Price: $10.0

Type:Trading Company

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Factory Supply Axitinib

Cas:319460-85-0

Min.Order:1

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Type:Other

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Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Factory Price API 99% Axitinib 319460-85-0 GMP Manufacturer

Cas:319460-85-0

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need C

Axitinib manufacturer with low price

Cas:319460-85-0

Min.Order:1 Gram

Negotiable

Type:Manufacturers

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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

Axitinib

Cas:319460-85-0

Min.Order:1 Kilogram

FOB Price: $5.0

Type:Manufacturers

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Shanghai Seasonsgreen Chemical Co.,Ltd

Shanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu

lower price High quality Axitinib

Cas:319460-85-0

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

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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

Axitinib

Cas:319460-85-0

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Hebei yanxi chemical co.,LTD.

chengdu and import and export trade co., LTD., who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do res

Axitinib

Cas:319460-85-0

Min.Order:1000 Gram

FOB Price: $6000.0

Type:Trading Company

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Hubei DiBo chemical co., LTD

Name:Axitinib The alias:N-Methyl-2-((3-((1E)-2-(pyridin-2-yl)ethenyl)-1H-indazol-6-yl)sulfanyl)benzamide; N-methyl-2-({3-[(E)-2-pyridin-2-ylethenyl]-1H-indazol-6-yl}sulfanyl)benzamide CAS NO: 319460-85-0 Molecular formula:C22H18N4OS Molecular wei

Axitinib/CAS:319460-85-0/Raw material supply

Cas:319460-85-0

Min.Order:25 Kilogram

FOB Price: $1.0 / 2.0

Type:Other

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Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 6 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O

319460-85-0 Axitinib

Cas:319460-85-0

Min.Order:1 Kilogram

FOB Price: $1000.0

Type:Lab/Research institutions

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LIDE PHARMACEUTICALS LIMITED

We are a professional chemicals, APIs and plant extract leading manufacturer in China. We are specialized in chemical synthesis, process development of pharmaceutical intermediates, active pharmaceutical ingredients (APIs), plant extract and rare

Axitinib

Cas:319460-85-0

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

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Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

Axitinib

Cas:319460-85-0

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

Type:Trading Company

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Zhuozhou Wenxi import and Export Co., Ltd

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

Pharmaceutical Grade CAS 319460-85-0 with competitive price

Cas:319460-85-0

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

GMP Factory Supply Axitinib CAS No.635702-64-6

Cas:319460-85-0

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Product name: Axitinib Cas Number: 319460-85-0 Moculer formula:C22H18N4OS Moculer weight: 386.47 Molar mass: 386.469 g/mol Appearance: Off-white powder Assay(By HPLC): ≥99.0% Axitinib is a small molecule tyrosine kinase inhibitor develo

Axitinib powder CAS:319460-85-0

Cas:319460-85-0

Min.Order:5 Metric Ton

FOB Price: $1.0 / 2.0

Type:Other

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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 containers

99% High Purity Axitinib Powder CAS: 319460-85-0 For Cancer Therapy

Cas:319460-85-0

Min.Order:100 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

Axitinib 319460-85-0

Cas:319460-85-0

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Leader Biochemical Group

About Product Details Items Specifications Test Results Appearance White to white crystalline powde

Supply High Quality Lubiprostone CAS 136790-76-6 For research Use only

Cas:319460-85-0

Min.Order:1 Gram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

inhibitor, Axitinib CAS:319460-85-0

Cas:319460-85-0

Min.Order:1 Gram

FOB Price: $27.0 / 32.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

Axitinib CAS:319460-85-0 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates,

Axitinib CAS:319460-85-0

Cas:319460-85-0

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

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

Axitinib

Cas:319460-85-0

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

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

CAS NO.:319460-85-0

Cas:319460-85-0

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Shanghai Terui OP New Material Technology Co., Ltd.

We have overseas warehouses in California, Nuevo Laredo, Mexico, Vancouver, Canada, Amsterdam, The Netherlands and Melbourne, Australia. Overseas warehouses can provide some of the best selling products. We look forward to cooperating with strong loc

Bulk supply cas 319460-85-0 Axitinib powder Safe delivery

Cas:319460-85-0

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

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Nanjing Fred Technology Co.,Ltd.

Nanjing Fred Technology Co., Ltd. is a professional R&D and manufacturer of API and pharmaceutical intermediates. We have professional team that can guarantee the quality. We can also provide a competitive price. We constantly satisfy the

Axitinib

Cas:319460-85-0

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

Axitinib 319460-85-0

Cas:319460-85-0

Min.Order:5 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

(E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide

(E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
With toluene-4-sulfonic acid In neat (no solvent) for 0.75h; Milling;99%
With toluene-4-sulfonic acid In methanol; water at 64℃; for 1 - 5h; Product distribution / selectivity;98%
With toluene-4-sulfonic acid In methanol; water at 65℃; for 4h; Reagent/catalyst; Inert atmosphere;95.4%
C22H18N4OS*C4H4O4

C22H18N4OS*C4H4O4

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
With 1,2-diaminopropan In 1-methyl-pyrrolidin-2-one at 40 - 70℃; for 1h;95%
6-[2-(methylcarbamoyl)phenylsulfanyl]-3-E-[2-(pyridin-2-yl)ethenyl]indazole ethylacetate solvate

6-[2-(methylcarbamoyl)phenylsulfanyl]-3-E-[2-(pyridin-2-yl)ethenyl]indazole ethylacetate solvate

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
In methanol; acetic acid at 60℃;92%
Stage #1: 6-[2-(methylcarbamoyl)phenylsulfanyl]-3-E-[2-(pyridin-2-yl)ethenyl]indazole ethylacetate solvate With toluene-4-sulfonic acid In ethanol at 82℃; for 14h;
Stage #2: With sodium hydrogencarbonate In ethanol; water at 20℃; for 2h;
6-[2-(methylcarbamoyl)phenylsulfanyl]-3-E-[2-(pyridin-2-yl)ethenyl]indazole p-toluene sulfonic acid salt

6-[2-(methylcarbamoyl)phenylsulfanyl]-3-E-[2-(pyridin-2-yl)ethenyl]indazole p-toluene sulfonic acid salt

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
In NaHCO3; ethyl acetate at 65℃;92%
2-vinylpyridine
100-69-6

2-vinylpyridine

2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide
885126-34-1

2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Stage #1: 2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide With palladium diacetate; acetic anhydride; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1-methyl-pyrrolidin-2-one at 25 - 50℃; Inert atmosphere;
Stage #2: 2-vinylpyridine In 1-methyl-pyrrolidin-2-one at 50 - 95℃; for 12h;
70.68%
With tris-(o-tolyl)phosphine; lithium bromide; palladium diacetate In 2,4-dichlorophenoxyacetic acid dimethylamine at 110℃; for 25h; Product distribution / selectivity; Heck Reaction;
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; tris-(o-tolyl)phosphine; lithium bromide; palladium diacetate In DMA at 110℃; for 25h; Product distribution / selectivity; Inert atmosphere;
bromobenzene
108-86-1

bromobenzene

tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
With triethylamine In neat (no solvent) at 100℃; for 24h; Heck Reaction; Green chemistry;70%
2-mercapto-N-methylbenzamide
20054-45-9

2-mercapto-N-methylbenzamide

(E)-6-bromo-3-(2-(pyridin-2-yl)vinyl)-1H-indazole

(E)-6-bromo-3-(2-(pyridin-2-yl)vinyl)-1H-indazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
With palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 48h; Inert atmosphere; Reflux;54%
2-vinylpyridine
100-69-6

2-vinylpyridine

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium diacetate; triethylamine; triphenylphosphine; tetrabutylammomium bromide; sodium bromide / neat (no solvent) / 1.5 h / Milling
2: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / neat (no solvent) / 0.83 h / Milling
3: toluene-4-sulfonic acid / neat (no solvent) / 0.75 h / Milling
View Scheme
2-vinylpyridine
100-69-6

2-vinylpyridine

N-1 Boc 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide

N-1 Boc 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Stage #1: 2-vinylpyridine; N-1 Boc 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide for 2h; Heck Reaction;
Stage #2: With tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 100℃;
Stage #3: With trifluoroacetic acid Product distribution / selectivity;
1,2-bis(diphenylphosphino)ethane; 6-[2-(methylcarbamoyl)phenylsulfanyl]-3-E-[2-(pyridine-2-yl)ethenyl]indazole; mixture of

1,2-bis(diphenylphosphino)ethane; 6-[2-(methylcarbamoyl)phenylsulfanyl]-3-E-[2-(pyridine-2-yl)ethenyl]indazole; mixture of

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
In tetrahydrofuran at 20 - 65℃; for 18h; Purification / work up;
N-methyl-2-((1-(t-butoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((1-(t-butoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
With trifluoroacetic acid In N,N-dimethyl-formamide
6-Iodo-1H-indazole
261953-36-0

6-Iodo-1H-indazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium hydrogencarbonate; tris-(dibenzylideneacetone)dipalladium(0) / 1-methyl-pyrrolidin-2-one / 0.5 h / 25 °C / Inert atmosphere; Large scale
1.2: 3 h / 25 - 50 °C / Inert atmosphere; Large scale
2.1: iodine; potassium hydroxide / 1-methyl-pyrrolidin-2-one; water / 5.5 h / 25 °C / Inert atmosphere; Large scale
3.1: N-ethyl-N,N-diisopropylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1-methyl-pyrrolidin-2-one / 50 °C / Inert atmosphere; Large scale
4.1: 1-methyl-pyrrolidin-2-one / 50 - 90 °C / Inert atmosphere; Large scale
5.1: 1,2-diaminopropan / water; tetrahydrofuran / 12.5 h / 50 °C / Inert atmosphere; Large scale
View Scheme
2-((1H-indazol-6-yl)thio)-N-methylbenzamide
944835-85-2

2-((1H-indazol-6-yl)thio)-N-methylbenzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: iodine; potassium hydroxide / 1-methyl-pyrrolidin-2-one; water / 5.5 h / 25 °C / Inert atmosphere; Large scale
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1-methyl-pyrrolidin-2-one / 50 °C / Inert atmosphere; Large scale
3: 1-methyl-pyrrolidin-2-one / 50 - 90 °C / Inert atmosphere; Large scale
4: 1,2-diaminopropan / water; tetrahydrofuran / 12.5 h / 50 °C / Inert atmosphere; Large scale
View Scheme
2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide
885126-34-1

2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1-methyl-pyrrolidin-2-one / 50 °C / Inert atmosphere; Large scale
2: 1-methyl-pyrrolidin-2-one / 50 - 90 °C / Inert atmosphere; Large scale
3: 1,2-diaminopropan / water; tetrahydrofuran / 12.5 h / 50 °C / Inert atmosphere; Large scale
View Scheme
N-methyl-2-((1-acetyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide
1639137-80-6

N-methyl-2-((1-acetyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
With 1,2-diaminopropan In tetrahydrofuran; water at 50℃; for 12.5h; Inert atmosphere; Large scale;28.0 kg
2-mercapto-N-methylbenzamide
20054-45-9

2-mercapto-N-methylbenzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium hydrogencarbonate; tris-(dibenzylideneacetone)dipalladium(0) / 1-methyl-pyrrolidin-2-one / 0.5 h / 25 °C / Inert atmosphere; Large scale
1.2: 3 h / 25 - 50 °C / Inert atmosphere; Large scale
2.1: iodine; potassium hydroxide / 1-methyl-pyrrolidin-2-one; water / 5.5 h / 25 °C / Inert atmosphere; Large scale
3.1: N-ethyl-N,N-diisopropylamine; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1-methyl-pyrrolidin-2-one / 50 °C / Inert atmosphere; Large scale
4.1: 1-methyl-pyrrolidin-2-one / 50 - 90 °C / Inert atmosphere; Large scale
5.1: 1,2-diaminopropan / water; tetrahydrofuran / 12.5 h / 50 °C / Inert atmosphere; Large scale
View Scheme
(E)-6-nitro-3-[(2-pyridin-2-yl)vinyl]-1H-indazole

(E)-6-nitro-3-[(2-pyridin-2-yl)vinyl]-1H-indazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: methanesulfonic acid / tetrahydrofuran / 6 h / Reflux
2.1: sodiumsulfide nonahydrate / water; methanol / 60 °C
3.1: acetic acid; sulfuric acid; sodium nitrite / water / 4 h / -5 - 0 °C
3.2: 5.5 h / 0 °C
4.1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
5.1: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
(Ε)-6-nitro-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-75-7

(Ε)-6-nitro-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodiumsulfide nonahydrate / water; methanol / 60 °C
2.1: acetic acid; sulfuric acid; sodium nitrite / water / 4 h / -5 - 0 °C
2.2: 5.5 h / 0 °C
3.1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
4.1: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1.1: ammonium chloride; iron / water; ethanol / 2 h / 50 °C
2.1: sodium nitrite; acetic acid / water / 2 h / 0 °C
2.2: 1.17 h / 0 °C
2.3: 2.08 h / 0 °C
3.1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
4.1: toluene-4-sulfonic acid / water; methanol / 4 h / 65 °C / Inert atmosphere
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid; sulfuric acid; sodium nitrite / water / 4 h / -5 - 0 °C
1.2: 5.5 h / 0 °C
2.1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
3.1: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium nitrite; acetic acid / water / 2 h / 0 °C
1.2: 1.17 h / 0 °C
1.3: 2.08 h / 0 °C
2.1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / water; methanol / 4 h / 65 °C / Inert atmosphere
View Scheme
6-nitroindazole
7597-18-4

6-nitroindazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate; iodine / N,N-dimethyl-formamide / 25 - 60 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 60 °C
3.1: potassium carbonate; 1,10-Phenanthroline; copper(l) iodide / N,N-dimethyl-formamide / 8 h / 60 - 100 °C / Inert atmosphere
3.2: 60 °C
4.1: methanesulfonic acid / tetrahydrofuran / 6 h / Reflux
5.1: sodiumsulfide nonahydrate / water; methanol / 60 °C
6.1: acetic acid; sulfuric acid; sodium nitrite / water / 4 h / -5 - 0 °C
6.2: 5.5 h / 0 °C
7.1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
8.1: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 2 h / 82 °C
2.1: sodium hydroxide; iodine / N,N-dimethyl-formamide / 14 h / 10 - 25 °C
2.2: 0.5 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium dichloride / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere
4.1: ammonium chloride; iron / water; ethanol / 2 h / 50 °C
5.1: sodium nitrite; acetic acid / water / 2 h / 0 °C
5.2: 1.17 h / 0 °C
5.3: 2.08 h / 0 °C
6.1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
7.1: toluene-4-sulfonic acid / water; methanol / 4 h / 65 °C / Inert atmosphere
View Scheme
(Ε)-6-iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(Ε)-6-iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

2-mercapto-N-methylbenzamide
20054-45-9

2-mercapto-N-methylbenzamide

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
2: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
2,2'-dithiobenzoic acid
119-80-2

2,2'-dithiobenzoic acid

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: thionyl chloride / N,N-dimethyl-formamide / 4 h / Reflux
2: tetrahydrofuran / 11 h / 0 - 20 °C / pH 9 - 10
3: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C
4: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
5: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
2,2'-dithiodibenzoic acid dichloride
19602-82-5

2,2'-dithiodibenzoic acid dichloride

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran / 11 h / 0 - 20 °C / pH 9 - 10
2: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C
3: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
4: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
2,2'-dithiobis(N-methylbenzamide)
2527-58-4

2,2'-dithiobis(N-methylbenzamide)

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C
2: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
3: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
3-iodo-6-nitro-1H-indazole
70315-70-7

3-iodo-6-nitro-1H-indazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 60 °C
2.1: potassium carbonate; 1,10-Phenanthroline; copper(l) iodide / N,N-dimethyl-formamide / 8 h / 60 - 100 °C / Inert atmosphere
2.2: 60 °C
3.1: methanesulfonic acid / tetrahydrofuran / 6 h / Reflux
4.1: sodiumsulfide nonahydrate / water; methanol / 60 °C
5.1: acetic acid; sulfuric acid; sodium nitrite / water / 4 h / -5 - 0 °C
5.2: 5.5 h / 0 °C
6.1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
7.1: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
1-acetyl-3-iodine-6-nitroindazole

1-acetyl-3-iodine-6-nitroindazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate; 1,10-Phenanthroline; copper(l) iodide / N,N-dimethyl-formamide / 8 h / 60 - 100 °C / Inert atmosphere
1.2: 60 °C
2.1: methanesulfonic acid / tetrahydrofuran / 6 h / Reflux
3.1: sodiumsulfide nonahydrate / water; methanol / 60 °C
4.1: acetic acid; sulfuric acid; sodium nitrite / water / 4 h / -5 - 0 °C
4.2: 5.5 h / 0 °C
5.1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
6.1: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aluminum (III) chloride / 1 h / 100 °C / Inert atmosphere
2: potassium hydroxide / methanol; water / 1.5 h / 20 °C
3: hydrogenchloride / methanol; water / 12 h / 50 °C
4: copper(I) oxide / i-Amyl alcohol / 5 h / Inert atmosphere; Reflux
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 50 °C
6: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 48 h / Inert atmosphere; Reflux
View Scheme
2,4-dibromoacetophenone
33243-33-3

2,4-dibromoacetophenone

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium hydroxide / methanol; water / 1.5 h / 20 °C
2: hydrogenchloride / methanol; water / 12 h / 50 °C
3: copper(I) oxide / i-Amyl alcohol / 5 h / Inert atmosphere; Reflux
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 50 °C
5: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 48 h / Inert atmosphere; Reflux
View Scheme
(E)-1-(2,4-dibromophenyl)-3-(pyridin-2-yl)prop-2-en-1-one

(E)-1-(2,4-dibromophenyl)-3-(pyridin-2-yl)prop-2-en-1-one

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride / methanol; water / 12 h / 50 °C
2: copper(I) oxide / i-Amyl alcohol / 5 h / Inert atmosphere; Reflux
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 50 °C
4: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 48 h / Inert atmosphere; Reflux
View Scheme
C21H16BrN3O2S

C21H16BrN3O2S

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 50 °C
2: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 48 h / Inert atmosphere; Reflux
View Scheme
axitinib
319460-85-0

axitinib

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

C22H18N4OS*C4H4O4

C22H18N4OS*C4H4O4

Conditions
ConditionsYield
With palladium In 1-methyl-pyrrolidin-2-one; ethanol at 65 - 75℃; for 1h; Solvent;99.9%
axitinib
319460-85-0

axitinib

acetyl chloride
75-36-5

acetyl chloride

N-methyl-2-((1-acetyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide
1639137-80-6

N-methyl-2-((1-acetyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 16h; Cooling with ice;99%
With triethylamine In dichloromethane at 20℃; for 16h; Cooling with ice; Inert atmosphere;99%
axitinib
319460-85-0

axitinib

2-((tert-butyldimethylsilyl)oxy)ethyl (4-nitrophenyl) carbonate

2-((tert-butyldimethylsilyl)oxy)ethyl (4-nitrophenyl) carbonate

C31H36N4O4SSi

C31H36N4O4SSi

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;98%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

axitinib
319460-85-0

axitinib

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-(tetrahydrofuran-2-yl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-(tetrahydrofuran-2-yl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 2h;96%
axitinib
319460-85-0

axitinib

p-nitrophenyl 13,13,14,14-tetramethyl-3,6,9,12-tetraoxa-13-silapentadec-1-yl carbonate

p-nitrophenyl 13,13,14,14-tetramethyl-3,6,9,12-tetraoxa-13-silapentadec-1-yl carbonate

N-methyl-2-((1-(13-hydroxy-1-oxo-2,5,8,11-tetraoxatridec-1-yl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide hydrochloride

N-methyl-2-((1-(13-hydroxy-1-oxo-2,5,8,11-tetraoxatridec-1-yl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide hydrochloride

Conditions
ConditionsYield
Stage #1: axitinib; p-nitrophenyl 13,13,14,14-tetramethyl-3,6,9,12-tetraoxa-13-silapentadec-1-yl carbonate With triethylamine In N,N-dimethyl-formamide at 20℃;
Stage #2: With hydrogenchloride; ethanol at 20℃; for 2h;
95.3%
axitinib
319460-85-0

axitinib

N-tert-butoxycarbonyl aspartic acid tert-butyl ester
34582-32-6

N-tert-butoxycarbonyl aspartic acid tert-butyl ester

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-(β-L-aspartyl)-1H-indazole-6-yl)thio)benzamide

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-(β-L-aspartyl)-1H-indazole-6-yl)thio)benzamide

Conditions
ConditionsYield
With diphenylphosphoranyl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 4h;93.6%
axitinib
319460-85-0

axitinib

N-tert-butoxycarbonyl aspartic acid tert-butyl ester
34582-32-6

N-tert-butoxycarbonyl aspartic acid tert-butyl ester

C31H31N5O6S

C31H31N5O6S

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 4h;93.6%
axitinib
319460-85-0

axitinib

formaldehyd
50-00-0

formaldehyd

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-hydroxymethyl-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-hydroxymethyl-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide at 0℃; for 3h;93%
axitinib
319460-85-0

axitinib

4-Nitrophenyl chloroformate
7693-46-1

4-Nitrophenyl chloroformate

C29H21N5O5S*(x)ClH

C29H21N5O5S*(x)ClH

Conditions
ConditionsYield
In tetrahydrofuran at 80℃; for 7h;92%
2-(2-(2-methoxyethoxy)ethoxy)ethyl (4-nitrophenyl) carbonate

2-(2-(2-methoxyethoxy)ethoxy)ethyl (4-nitrophenyl) carbonate

axitinib
319460-85-0

axitinib

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-((3,6,9-trioxadecane-1-yl)oxycarbonyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-((3,6,9-trioxadecane-1-yl)oxycarbonyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;89%
With triethylamine In N,N-dimethyl-formamide at 20℃;89%
axitinib
319460-85-0

axitinib

(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)ethyl)(4-nitrophenyl) carbonate

(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)ethyl)(4-nitrophenyl) carbonate

N-methyl-2-((1-(2-(2-hydroxyethoxy)ethoxycarbonyl)-3-(( 1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide hydrochloride

N-methyl-2-((1-(2-(2-hydroxyethoxy)ethoxycarbonyl)-3-(( 1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide hydrochloride

Conditions
ConditionsYield
Stage #1: axitinib; (2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)ethyl)(4-nitrophenyl) carbonate With triethylamine In N,N-dimethyl-formamide at 20℃;
Stage #2: With hydrogenchloride; ethanol at 20℃; for 2h;
87.8%
axitinib
319460-85-0

axitinib

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-methyl-2-((1-(t-butoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((1-(t-butoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;87%
With triethylamine In N,N-dimethyl-formamide at 20℃;77%
With triethylamine In N,N-dimethyl-formamide for 1h;4.1 g
With triethylamine In N,N-dimethyl-formamide for 1h;4.1 g
With triethylamine In N,N-dimethyl-formamide for 1h;4.1 g
axitinib
319460-85-0

axitinib

t-butyl malonate
541-16-2

t-butyl malonate

N-methyl-2-((1-(t-butoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((1-(t-butoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;87%
axitinib
319460-85-0

axitinib

axitinib hydrobromic acid salt

axitinib hydrobromic acid salt

Conditions
ConditionsYield
With hydrogen bromide In isopropyl alcohol at 20 - 50℃;84%
axitinib
319460-85-0

axitinib

p-nitrophenyl 13,13,14,14-tetramethyl-3,6,9,12-tetraoxa-13-silapentadec-1-yl carbonate

p-nitrophenyl 13,13,14,14-tetramethyl-3,6,9,12-tetraoxa-13-silapentadec-1-yl carbonate

N-methyl-2-((1-(13,13,14,14-tetramethyl-3,6,9,12-tetraoxa-13-silapentadec-1-yl)-3-(( 1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((1-(13,13,14,14-tetramethyl-3,6,9,12-tetraoxa-13-silapentadec-1-yl)-3-(( 1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;83.1%
axitinib
319460-85-0

axitinib

axitinib hydrochloric acid salt

axitinib hydrochloric acid salt

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol at 20 - 50℃;83%
axitinib
319460-85-0

axitinib

1-dodecyl p-nitrophenyl carbonate
66398-02-5

1-dodecyl p-nitrophenyl carbonate

N-methyl-2-((1-dodecyloxycarbonyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((1-dodecyloxycarbonyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;82.3%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;82.3%
axitinib
319460-85-0

axitinib

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

6-((2-((t-butoxycarbonyl)(methyl)carbamoyl)phenyl)thio)-3-(2-(pyridin-2-yl)ethylenyl)-1H-indazol-1-carboxylic acid (E)-t-butyl ester

6-((2-((t-butoxycarbonyl)(methyl)carbamoyl)phenyl)thio)-3-(2-(pyridin-2-yl)ethylenyl)-1H-indazol-1-carboxylic acid (E)-t-butyl ester

Conditions
ConditionsYield
With dmap In dichloromethane at 25℃; for 16h;81.9%
axitinib
319460-85-0

axitinib

methanesulfonic acid
75-75-2

methanesulfonic acid

axitinib methanesulfonic acid salt

axitinib methanesulfonic acid salt

Conditions
ConditionsYield
In isopropyl alcohol at 20 - 50℃;81%
axitinib
319460-85-0

axitinib

pivaloyl chloride
3282-30-2

pivaloyl chloride

N-methyl-2-((1-pivaloyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((1-pivaloyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;81%
With triethylamine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice;81%
axitinib
319460-85-0

axitinib

4-nitrophenyl (2,2,3,3-tetramethyl-4,7,10-trioxa-3-siladodecan-12-yl) carbonate

4-nitrophenyl (2,2,3,3-tetramethyl-4,7,10-trioxa-3-siladodecan-12-yl) carbonate

C35H44N4O6SSi

C35H44N4O6SSi

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide81%
axitinib
319460-85-0

axitinib

N-methyl-2-((1-(2-(2-(tert-butyldimethylsilyloxy)ethoxy)ethoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((1-(2-(2-(tert-butyldimethylsilyloxy)ethoxy)ethoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;81%
axitinib
319460-85-0

axitinib

(2-(2-methoxyethoxy)ethyl) (4-nitrophenyl) carbonate
105108-59-6

(2-(2-methoxyethoxy)ethyl) (4-nitrophenyl) carbonate

N-methyl-2-((1-(1-oxo-2,5,8-trioxanayl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((1-(1-oxo-2,5,8-trioxanayl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;80.6%
axitinib
319460-85-0

axitinib

4-nitrophenyl (2,2,3,3-tetramethyl-4,7,10-trioxa-3-siladodecan-12-yl) carbonate

4-nitrophenyl (2,2,3,3-tetramethyl-4,7,10-trioxa-3-siladodecan-12-yl) carbonate

N-methyl-2-((1-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide hydrochloride

N-methyl-2-((1-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxycarbonyl)-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide hydrochloride

Conditions
ConditionsYield
Stage #1: axitinib; 4-nitrophenyl (2,2,3,3-tetramethyl-4,7,10-trioxa-3-siladodecan-12-yl) carbonate With triethylamine In N,N-dimethyl-formamide at 20℃;
Stage #2: With hydrogenchloride; ethanol at 20℃; for 2h;
79.8%
axitinib
319460-85-0

axitinib

methyl (2-ethoxy)(4-nitrophenyl)carbonate
426264-10-0

methyl (2-ethoxy)(4-nitrophenyl)carbonate

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-((2-methoxy-1-ethyl)oxycarbonyl)-1H-indazol-6-yl)thio)benzamide

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-((2-methoxy-1-ethyl)oxycarbonyl)-1H-indazol-6-yl)thio)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;79.8%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;79.8%
axitinib
319460-85-0

axitinib

4-nitrophenyl n-pentyl carbonate
67036-14-0

4-nitrophenyl n-pentyl carbonate

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-pentyloxycarbonyl-1H-indazol-6-yl)sulfanyl)benzamide

N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-pentyloxycarbonyl-1H-indazol-6-yl)sulfanyl)benzamide

Conditions
ConditionsYield
With triethylamine at 20℃; for 3h;77%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;77%

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