Phenylacetylene → 3-Methyl-5-phenylethynylpyridine

Participants

Reaction Conditions

Reaction Steps

Add phenylacetylene (0.460 mL, 4.2 mmol), copper (I) iodide (0.072 g, 0.38 mmol) and bis(triphenylphosphine)palladium (II) dichloride (0.133 g, 0.19 mmol) to a solution of 3-bromo-5-methylpyridine, (prepared essentially as described in PREPARATION 1), (0.654 g, 3.8 mmol) in degassed triethylamine (20 mL) and stir under nitrogen at 80° C. for 16 h. Cool the reaction mixture to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with 80:20 hexanes:ethyl acetate, to give the title compound as a brown oil (0.398 g, 54%).

Provenance & Evidence