Triethylamine → 3-(3,4-Difluorophenylethynyl)-5-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

Add bis(triphenylphosphine)palladium (II) dichloride (110 mg, 0.15 mmol), copper (I) iodide (57 mg, 0.30 mmol), and 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (400 mg, 3.0 mmol) to a solution of 1,2-difluoro-4-iodobenzene (0.43 mL, 3.6 mmol) in triethylamine (6.3 mL, 45.0 mmol) and heat at 60° C. for 20 h. Cool to room temperature and concentrate. Purify the residue by silica gel chromatography, eluting with 100:0 to 65:35 hexanes:ethyl acetate, followed by a second silica gel chromatography, eluting with 100:0 to 80:20 dichloromethane:ethyl acetate, to give the title compound as a white solid (690 mg, 94%).

Provenance & Evidence