4-Bromotoluene → 5-(Benzyloxy)-3-p-tolyl-3H-imidazo[4,5-b]pyridine

Participants

Reaction Steps

5-(Benzyloxy)-3H-imidazo[4,5-b]pyridine (0.204 g, 0.906 mmol), 4-bromotoluene (0.123 mL, 0.996 mmol), potassium carbonate (263 mg, 1.90 mmol), copper(1) iodide (8.6 mg, 0.045 mmol) and NMP (3 mL) were heated at 210° C. for 1 h under microwave irradiation in a heavy walled sealed tube. The mixture was cooled to room temperature and diluted with EtOAc. The solution was washed with water and the organics were dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give a mixture of the title compound and its regioisomer 5-(benzyloxy)-1-p-tolyl-1H-imidazo[4,5-b]pyridine (154 mg). LCMS m/z=316.3 [M+H]+.

Provenance & Evidence