Sodium Carbonate → 7-Bromo-4-chloro-2-phenylthieno[3,2-c]pyridine

Participants

Reaction Steps

A mixture of 7-bromo-2-phenyl-5H-thieno[3,2-c]pyridin-4-one 3 (2.28 g, 7.5 mmol) in phosphorus oxychloride (27 mL) was heated at reflux for 21 h. The reaction mixture was basified to pH 5–6 by the addition of saturated aqueous sodium carbonate and extracted with dichloromethane (1×). The organic layer was dried over Na2SO4, filtered, and the filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 97:3) to give 95. 1H NMR (400 MHz, CDCl3) δ: 7.41–7.52 (m, 3H), 7.72–7.78 (m, 3H), 8.28 (s, 1H). MS (EI) m/z (M+H+) 324.

Provenance & Evidence