Ethyl 3-(3,5-dibromopyridin-4-yl)propanoate → 4-bromo-5H,6H,7H-cyclopenta[c]pyridin-7-one

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-(3,5-dibromopyridin-4-yl)propanoate (30 g, 89 mmol) in THF (50 mL) was added slowly n-BuLi (71.2 mL, 178 mmol, 2.5 M in hexane) at −78° C. The resulting mixture was stirred for another 30 min at −78° C. before it was quenched with water, and extracted with EtOAc (500 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product which was purified by column chromatography (n-pentane:EtOAc=5:1) to give title compound (7 g, 37%) as a white solid. MS: 211.8 (M+H+, 1 Br).

Provenance & Evidence