To a degassed solution of methyl 3-ethynyl-5-(5-methylpyridin-2-yl)benzoate (124 mg, 0.493 mmol) in benzene (12 mL) were added trimethylsilylmethylazide (96 mg, 0.740 mmol) and pentamethylcyclopentadienylbis(triphenylphosphine)ruthenium(II) chloride (59 mg, 0.074 mmol) and the mixture heated to 80° C. in a sealed tube. After 16 h, the title compound was showed as the major isomer (10:1 isomeric ratio) in the reaction. The reaction was concentrated and purified by reverse-phase HPLC gave the title compound (120 mg). MS 381.1 (M+1).
