Sodium Carbonate → 3-(1-Boc-2-(r)-pyrrolidinylmethoxy)-5-(4-chlorophenyl)pyridine

Participants

Reaction Steps

To a solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine (280 mg, 0.79 mmol) and 4-chlorophenylboronic acid (246 mg, 1.57 mmol, Lancaster Chemical Co.) in toluene (10 mL) was added Pd(0) (30 mg) and Na2CO3 (2.5 mL of a 2 M solution), and the mixture was heated at reflux for 6 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 (370 mg, >100% yield): 1H NMR (CDCl3, 300 MHz) δ1.47 (s, 9H), 1.80-2.10 (m, 3H), 3..30-3.49 (m, 2H), 3.90-4.30 (m, 3H), 7.40-7.60 (m, 5H), 8.31 (s, 1H), 8.42 (s, 1H); MS (CI/NH3) m/z 389 (M+H)+.

Provenance & Evidence