ChemicalBook CAS DataBase List Axitinib Impurity B

Axitinib Impurity B synthesis

7synthesis methods

Product Name:Axitinib Impurity B
CAS Number:944835-85-2
Molecular formula:C15H13N3OS
Molecular Weight:283.35

261953-36-0 Synthesis

261953-36-0
259 suppliers
$9.00/250mg

20054-45-9 Synthesis

20054-45-9
159 suppliers
$139.00/250mg

944835-85-2
70 suppliers
$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