Triethylamine → 3-{[(6-Bromopyridin-2-yl)methyl]amino}cyclopent-2-en-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(6-bromopyridin-2-yl)methanamine hydrochloride (500 mg, 2.24 mmol) in toluene (10 ml) was charged with triethylamine (0.31 ml, 2.24 mmol). The reaction was stirred for 5 minutes after which cyclopentane-1,3-dione (330 mg, 3.36 mmol) and p-toluenesulfonic acid monohydrate (43 mg, 0.022 mmol) were added. The reaction mixture was heated to reflux at 95° C. for 45 minutes. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (15 ml), 2N sodium hydroxide (10 ml) and brine (10 ml). The layers were separated and the organic layer was then dried over sodium sulfate, filtered and concentrated to yield the title compound.

Provenance & Evidence