Sodium Carbonate → 3-(1-Boc-2-(r)-azetidinylmethoxy)-6-chloro-5-phenylpyridine

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To a mixture of 3-(1-BOC-2-(R)-azetidinylmethoxy)-5-bromo-6-chloropyridine (0.25 g, 0.68 mmol), tetrakis(triphenylphosphine)palladium(0) (25 mg, 1%), aqueous sodium carbonate (2.0 M, 1 mL) in toluene (10 mL), was added phenylboronic acid (0.108 g, 0.89 mmol). The reaction mixture was stirred and heated at 90° C. for 16 h. Solvent was evaporated. The residue was chromatographed (silica gel; hexane/EtOAC, 10:1 to 2:1) to afford an oil (0.20 g, 78%): 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 4H), 1.58 (s, 5H), 2.24-2.40 (m, 2H), 3.89 (t, 2H, J=7.5 Hz), 4.15 (dd, 1H, J=3.0, 10.0 Hz), 4.36 (m, 1H), 4.52 (m, 1H), 7.27 (d, 1H, J=3.0 Hz), 7.45 (s, 5H), 8.12 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 347 (M+H)+.

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