Triethylamine → 3-Bromo-5-phenylethynylpyridine

Participants

Reaction Steps

Add phenylacetylene (1.11 mL, 10.10 mmol) dropwise to a mixture of 3,5-dibromopyridine (2.05 g, 8.65 mmol), bis(triphenylphosphine)palladium (II) dichloride (300 mg, 0.427 mmol), and copper (I) iodide (160 mg, 0.840 mmol) in triethylamine (8.50 mL, 60.98 mmol) and stir for 3 h at room temperature. Dilute the reaction mixture with ethyl acetate and wash with a saturated aqueous solution of sodium chloride. Dry (sodium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient of 100:0 to 90:10 hexanes:ethyl acetate, to give the title compound (710 mg, 32%).

Provenance & Evidence