Reaktion #166198

Reaktionsgleichung

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

iodine monochloride

→

title compound

Ausbeute 83.0%

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

Ausbeute 83.0%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe 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
   ExtraktionThe resultant mixture was extracted with ethyl acetate (3×20 mL)
4. 4
   Waschenthe combined organic fractions washed with brine (20 mL)
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenthen concentrated in vacuo

Vorschrift

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.

Quelle