Triethylamine → 3-Chloro-5-(4-fluoro-3-nitrophenylethynyl)-pyridine

Participants

Reaction Conditions

Reaction Steps

Add bis(triphenylphosphine)palladium (II) dichloride (150 mg, 0.22 mmol), copper (I) iodide (83 mg, 0.44 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (600 mg, 4.4 mmol) to a solution of 1-fluoro-4-iodo-2-nitrobenzene, (prepared as described in PREPARATION 46), (1.22 g, 4.6 mmol) in triethylamine (6.6 mL, 65.3 mmol). Stir at 60° C. for 18 h then concentrate. Purify by silica gel chromatography, eluting with a gradient of 100:0 to 90:10 dichloromethane:ethyl acetate, followed by a second silica gel chromatography, eluting with 95:5 to 60:40 hexanes:ethyl acetate, to give the title compound as a light yellow solid (650 mg, 54%).

Provenance & Evidence