Triethylamine → 3-(1-Boc-2-(s)-azetidinylmethoxy)-6-chloro-5-(trimethylsilylethynyl)pyridine

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To a solution of 3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-chloropyridine (1.0 g, 2.6 mmol) in toluene (20 mL) was added NEt3 (1 mL), copper (I) iodine (50 mg, 10%), tetrakis(triphenylphosphine)palladium (0) (305 mg, 10%) and (trimethylsilyl)acetylene (0.45 mL, 3.18 mmol). The reaction mixture was stirred and heated at 100° C. for 16 h. Solvent was evaporated and the residue was chromatographed (silica gel; hexane/EtoAc, 5:1 to 2:1) to afford an oil (770 mg, 74%): 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.20-2.40 (m, 2H), 3.80-3.92 (m, 2H), 4.10 (m, 1H), 4.30 (m, 1H), 4.50 (m, 1H), 7.37 (d, 1H, J=3.0 Hz), 8.05 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 395 (M+H)+.

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