Sodium Carbonate → 5-Methoxy-7-phenylimidazo[1,2-a]pyridine

Participants

Reaction Conditions

Reaction Steps

7-iodo-5-methoxyimidazo[1,2-a]pyridine (539 mg, 1.97 mmol), phenylboronic acid (719 mg, 5.90 mmol), tetrakis(triphenylphosphine)palladium (0) (227 mg, 0.197 mmol), and sodium carbonate (625 mg, 5.90 mmol) were added to a dry flask. Dioxane (18 ml) and water (2 ml) were added and the reaction mixture was sparged with argon for 5 minutes. The reaction mixture was heated to 85° C. After 16 h, the reaction mixture was cooled, diluted with ethyl acetate, washed with water, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (methanol/dichloromethane gradient) to give 5-methoxy-7-phenylimidazo[1,2-a]pyridine. LRMS (ESI) calculated for C14H13N2O [M+H]+, 225.1 found 225.0.

Provenance & Evidence