Sodium Carbonate → 3-(2-(S)-Azetidinylmethoxy)-6-chloro-5-(4-chlorophenyl)pyridine

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Reaction Steps

To a solution of 3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-chloropyridine (650 mg, 1.73 mmol) and 4-chlorophenylboronic acid (284 mg, 1.82 mmol, Lancaster Chemical Co.) in toluene (10 mL) was added Pd(0) (37 mg) and Na2CO3 (5 mL of a 2 M solution), and the mixture was heated at reflux for 14 h. The solvent was removed under vacuum, and the residue was chromatographed (silica gel; EtOAc/hexane, 1:5 to 1:2) to afford the title compound (665 mg, 94 % yield): 1H NMR (CDCl3, 300 MHz) δ1.41 (s, 9H), 2.23-2.44 (m, 2H), 3.89 (t, J=7.5, Hz, 2H), 4.08-4.18 (m, 2H), 4.37 (m, 1H), 4.53 (m, 1H), 7.25 (d, J=3.0 Hz, 1H), 7.37-7.46 (m, 4H), 8.13 (d, J=3.0 Hz, 1H); MS (CI/NH3) m/z 409 (M+H)+.

Provenance & Evidence