Water → N-[4-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-yl)-phenyl]methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]methanesulfonamide (85 mg, 0.23 mmol) in CH2Cl2 (2 mL) was cooled to −5° C. A solution of boron tribromide (1.15 mL, 1.15 mmol, 1M solution in CH2Cl2) was added and the reaction mixture was allowed to warm to 110° C. over 4 h. The reaction mixture was poured into H2O and extracted with EtOAc (3×). The combined organic phases were washed with H2O and saturated NaCl and dried and concentrated. Chromatography over silica gel (EtOAc/CH2Cl2, 5-10%) gave 18 mg (22%) of N-[4-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-yl)-phenyl]methane sulfonamide as a tan solid.

Provenance & Evidence