1.5 mL of toluene suspension containing 0.15 g of methyl 2-(benzamido)-4-ethynylbenzoate, 0.090 mL of iodinated benzene, 5 mg of copper(I) iodide, 20 mg of bis(triphenylphosphine)palladium(II) chloride and 0.15 mL of triethylamine was stirred under nitrogen atmosphere at room temperature for 2 hours. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=8:1] to obtain 0.13 g of methyl 2-(benzamido)-4-(phenylethynyl)benzoate as white solid.
