반응 #166198

반응 방정식

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

iodine monochloride

→

title compound

수율 83.0%

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

수율 83.0%

용매

DCM

DCM

반응 조건

후처리

1. 1
   기타The 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
   추출The resultant mixture was extracted with ethyl acetate (3×20 mL)
4. 4
   세척the combined organic fractions washed with brine (20 mL)
5. 5
   건조dried (MgSO4)
6. 6
   농축then concentrated in vacuo

실험 절차

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.

출처