1,4-Dioxane → Methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

3-iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine (166 mg, 0.474 mmol), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (254 mg, 0.948 mmol), tetrakis(triphenylphosphine)palladium (0) (55.0 mg, 0.047 mmol), and sodium bicarbonate (150 mg, 1.42 mmol) were added to a dry flask. Dioxane (5 ml) and water (0.5 ml) were added and the reaction mixture was sparged with argon for 3 minutes. The reaction mixture was heated to 90° C. After 6 h the reaction mixture was cooled to ambient temperature, 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 (ethyl acetate/dichloromethane gradient) to give methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate. LRMS (ESI) calculated for C20H17N2O3S [M+H]+, 365.1 found 365.0.

Provenance & Evidence