Triethylamine → 3-Chloro-5-[2-(trimethylsilyl)ethynyl]pyridine

Participants

Reaction Conditions

Reaction Steps

Sequentially add triethylamine (16 mL, 114 mmol), trimethylsilyl acetylene (4.5 mL, 34.1 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.538 g, 0.77 mmol), and copper (I) iodide (270 mg, 1.42 mmol) to a solution of trifluoromethanesulfonic acid 5-chloropyridin-3-yl ester (7.4 g, 28.4 mmol), (prepared as described in PREPARATION 25), in ethyl acetate (25 mL) under nitrogen. Heat at 60° C. for 1 h, cool to room temperature, stir for 12 h, filter through diatomaceous earth and wash with diethyl ether. Concentrate and purify the residue by silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes, to give the title compound as an orange oil (5.51 g, 92%).

Provenance & Evidence