A mixture of 5-ethoxycarbonyl-7-iodo-1-phenylbenzimidazole (0.70 g, 1.8 mmol), 3-acetamidophenylboronic acid (0.48 g, 2.7 mmol), 1,3-propanediol (0.65 ml, 8.9 mmol), potassium carbonate (1.23 g, 8.9 mmol) and bis(triphenylphosphin)palladium dichloride (50 mg, 0.07 mmol) in a mixture of dimethoxyethane (10 ml) and water (5 ml) was stirred at reflux for 1 hour. The cooled reaction mixture was concentrated under reduced pressure, and the concentrate was partitioned between water and ethyl acetate. The organic phase was dried and concentrated under reduced pressure, and the concentrate was triturated in ethyl acetate leaving the product as an off-white solid (0.48 g, 67%) m/z, 400.2 (M+H)+.
