Dimethylamine → 2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

Participants

Reaction Steps

To a solution of 5-bromoindole (15.85 g, 81 mmol) in tetrahydrofuran (80 ml) at 0-5° C. under an atmosphere of nitrogen was added oxalyl chloride (7.76 ml 89 mmol) dropwise, maintaining the temperature below 5° C. The cloudy solution was then warmed to ambient temperature and stirred for 30 min, before being re-cooled to 0-5° C. The solution was then saturated with anhydrous dimethylamine for 30 min, which resulted in formation of a yellow precipitate. The slurry was then warmed to ambient temperature and diluted with demineralised water (100 ml) before being extracted with dichloromethane (3×50 ml). The organic extracts were combined and evaporated in vacuo to give a white solid. This was slurried in a mixture of ethyl acetate:hexane (1:1) (40 ml) for 8 hr and then filtered in vacuo to give the subtitle compound (20.28 g, 85%) as a white solid. m.p. 189-190° C.

Provenance & Evidence