Triethylamine → 3-Methoxy-5-[(trimethylsilyl)ethynyl]pyridine

Participants

Reaction Steps

Add (trimethylsilyl)acetylene (1.3 mL, 9.45 mmol) and bis(triphenylphosphine)palladium (II) dichloride (0.102 g, 0.15 mmol) to a mixture of 3-bromo-5-methoxypyridine from PREPARATION 9 (1.366 g, 7.26 mmol), copper (I) iodide (0.055 g, 0.29 mmol) and triethylamine (4.1 mL, 29.04 mmol) in ethyl acetate (7.5 mL) in a sealed tube. Stir the resultant reaction mixture at 75° C. for 20 h and cool to room temperature. Dilute the reaction mixture with ethyl acetate and filter through a pad of diatomaceous earth. Wash with ethyl acetate and concentrate the filtrate to give the title compound as a solid which is used without further purification (1.48 g, 100%).

Provenance & Evidence