Hydrochloric Acid → HCID 58404774, compound

Participants

Reaction Steps

To a solution of bromoacetaldehyde dimethyl acetal (0.16 mL, 1.38 mmol) in water (2 mL) was added hydrochloric acid (0.046 mL, 0.276 mmol). After stirring at room temperature for 2 hours, the reaction was heated to 80° C. for 40 mins to give a clear solution. The reaction was cooled down to room temperature, and sodium bicarbonate (147 mg, 1.75 mmol) was added, followed by a solution of 6-(benzyloxy)-4-phenylpyridin-2-amine (254 mg, 0.919 mmol) in 1,4-dioxane (2 mL). The reaction was stirred overnight at ambient temperature, then diluted with ethyl acetate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to give 5-(benzyloxy)-7-phenylimidazo[1,2-a]pyridine. LRMS (ESI) calculated for C20H17N2O [M+H]+, 301.1; found 301.0.

Provenance & Evidence