تفاعل #166198

معادلة التفاعل

4-(2-fluoro-4-trimethylsilanylphenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl ester

iodine monochloride

→

title compound

المردود 83.0%

4-(2-Fluoro-4-iodophenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl ester

المردود 83.0%

المذيبات

DCM

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched by the addition of water (10 mL)
2. 2
   workup.ADDITIONthen diluted with saturated aqueous sodium thiosulfate solution (10 mL)
3. 3
   استخلاصThe resultant mixture was extracted with ethyl acetate (3×20 mL)
4. 4
   غسيلthe combined organic fractions washed with brine (20 mL)
5. 5
   تجفيفdried (MgSO4)
6. 6
   تركيزthen concentrated in vacuo

الإجراء التجريبي

To a solution of 4-(2-fluoro-4-trimethylsilanylphenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl ester (0.56 g, 1.1 mmol) in DCM (3 mL) at 0° C. was added a solution of iodine monochloride in DCM (2.2 mL, 1M, 2.2 mmol). The reaction mixture was stirred at 0° C. for 30 minutes. The reaction was quenched by the addition of water (10 mL) then diluted with saturated aqueous sodium thiosulfate solution (10 mL). The resultant mixture was extracted with ethyl acetate (3×20 mL) and the combined organic fractions washed with brine (20 mL), dried (MgSO4) then concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0-100% DCM in cyclohexane) to yield the title compound as a light brown solid (0.51 g, 83%). LCMS (Method B): RT=4.87 min, [M+H]+=566.

المصدر