Triethylamine → 5-(5-Chloropyridin-3-ylethynyl)-2-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

Add bis(triphenylphosphine)palladium (II) dichloride (77 mg, 0.11 mmol), copper (I) iodide (42 mg, 0.22 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (300 mg, 2.2 mmol) to a solution of 2-fluoro-5-iodobenzonitrile (650 mg, 2.6 mmol) in triethylamine (4.6 mL, 33 mmol) and heat at 60° C. for 6 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 50:50 dichloromethane:hexanes to 90:10 dichloromethane:ethyl acetate, followed by a second silica gel chromatography eluting with 95:5 to 75:25 hexanes:ethyl acetate, to give the title compound as an off-white solid (510 mg, 91%).

Provenance & Evidence