Réaction #166198

Équation de réaction

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

iodine monochloride

→

title compound

Rendement 83.0%

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

Rendement 83.0%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   AutreThe 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
   ExtractionThe resultant mixture was extracted with ethyl acetate (3×20 mL)
4. 4
   Lavagethe combined organic fractions washed with brine (20 mL)
5. 5
   Séchagedried (MgSO4)
6. 6
   Concentrationthen concentrated in vacuo

Mode opératoire

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.

Source