Axitinib Impurity B synthesis
- Product Name:Axitinib Impurity B
- CAS Number:944835-85-2
- Molecular formula:C15H13N3OS
- Molecular Weight:283.35
261953-36-0
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20054-45-9
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944835-85-2
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$617.00/1g
Yield: 96%
Reaction Conditions:
with tris-(dibenzylideneacetone)dipalladium(0);cesiumhydroxide monohydrate;4,5-bis(diphenylphosphino)-9,9-dimethylxanthene in N,N-dimethyl-formamide at 100; for 4.5 h;Inert atmosphere;
Steps:
62 Production of 2-{(1H-indazol-6-yl)thio}-N-methylbenzamide
N,N-Dimethylformamide (25 mL) was added to 6-iodo-1H-indazole (5.51 g, 22 mmol), 2-mercapto-N-methylbenzamide(5.16 g, 31 mmol), Pd2(dba)3 (1.02 g, 1.1 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (1.46 g,2.5 mmol) and cesium hydroxide monohydrate (5.67 g, 33 mmol) and stirred under an argon atmosphere at 100°C for4.5 hours. The solvent was distilled away from the reaction solution under a reduced pressure, the residue was dissolvedin ethyl acetate and washed with water and saturated saline. The organic layer was dried with anhydrous sodium sulfate,and the solvent was distilled away under a reduced pressure. The residue was purified by silica gel column chromatography(hexane/ethyl acetate (v/v) = 1/3) to obtain the title compound (6.14 g, 96%) as a pale orange solid.1H NMR (400 MHz, DMSO-d6) δ 13.13 (1H, br s), 8.36 (1H, br q, J = 4.4 Hz), 8.10 (1H, s), 7.78 (1H, br d, J = 8.4 Hz),7.59 (1H, br s), 7.48-7.46 (1H, m), 7.29 (1H, td, J = 7.6, 1.6 Hz), 7.25 (1H, td, J = 7.6, 1.6 Hz), 7.08 (1H, dd, J = 8.4, 1.6Hz), 6.99-6.97 (1H, m), 2.76 (3H, d, J = 4.4 Hz)
References:
Senju Pharmaceutical Co., Ltd.;TAKEDA, Norihiko;MIYABE, Tomoyo;MACHIDA, Shinnosuke;MACHIDA, Mamiko;NAKAJIMA, Takeshi EP3127900, 2017, A1 Location in patent:Paragraph 0252; 0253
1266386-30-4
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20054-45-9
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944835-85-2
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$617.00/1g
![2,2'-dithiobis[N-methylbenzamide]](http://hg.y866.cn/chemistry/CAS/GIF/2527-58-4.gif)
2527-58-4
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944835-85-2
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6967-12-0
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944835-85-2
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19602-82-5
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$144.00/1mg
944835-85-2
70 suppliers
$617.00/1g