Water → HCID 21191894, compound

Participants

Reaction Steps

A solution of 483 mg (1.4 mmol) of 1-[(3-chlorophenyl) methyl]-5-methoxy-2-methyl-1H-indole-3-acetamide and 5.6 mL of 1M BBr3/methylene chloride in 20 mL of methylene chloride was stirred for 5 hours, 2 mL of 1M BBr3/methylene chloride added and stirred 16 hours. The mixture was poured into water, extracted with ethyl acetate, the ethyl acetate solution washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted using a gradient, 50% EtOAc/hexane→4EtOAc, to give 155 mg of starting material, 1-[(3-chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetamide, and 220 mg (48% yield) of 1-[(3-chlorophenyl)methyl]-5-hydroxy-2-methyl-1H-indole-3-acetamide, mp, 173-177° C.

Provenance & Evidence