Water → methyl 6-bromo-1-isopropyl-1H-indole-3-carboxylate

Participants

Reaction Steps

To a solution of 6-bromo-1-isopropyl-1H-indole-3-carboxylic acid (1.94 g) in N,N-dimethylformamide (97 ml) were added potassium carbonate (1.43 g) and iodomethane (0.514 ml) at room temperature under nitrogen, and the mixture was stirred at the same temperature for 3.5 hours. The resulting mixture was poured into water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with water three times and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10/1 to 5/1) to give methyl 6-bromo-1-isopropyl-1H-indole-3-carboxylate (1.9 g).

Provenance & Evidence