反应 #166198

反应方程式

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

iodine monochloride

→

title compound

收率 83.0%

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

收率 83.0%

溶剂

DCM

DCM

反应条件

后处理

1. 1
   其他The 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
   萃取The resultant mixture was extracted with ethyl acetate (3×20 mL)
4. 4
   洗涤the combined organic fractions washed with brine (20 mL)
5. 5
   干燥dried (MgSO4)
6. 6
   浓缩then concentrated in vacuo

实验过程

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.

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