Triethylamine → ethyl 7-bromo-3-(3-oxopropyl)-1H-indole-2-carboxylate

Participants

Reaction Steps

To a solution of ethyl 7-bromo-3-(4-hydroxypropyl)-1H-indole-2-carboxylate (EXAMPLE 1C) (3.4 g) and triethylamine (8.5 ml) in dichloromethane (100 ml) and dimethylsulfoxide (10 mL), cooled to 0° C., was added pyridine-2-sulfonate (9.54 g). The mixture was stirred for 3 hours and diluted with ethyl acetate (300 ml) and washed with 5% HCl, water, and brine. After drying the combined organic layers over Na2SO4, the filtrate was concentrated and the crude product was purified by flash chromatography on a silica gel, eluting with 10% ethyl acetate in hexane.

Provenance & Evidence