4-Vinylpyridine → 3-(1-Boc-2-(s)-pyrrolidinyl-methoxy)-5-(4-pyridinyl-ethenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine (300 mg, 0.84 mmol) in acetonitrile (10 mL) and NEt3 (1 mL) was added 4-vinylpyridine(0.15 mL, 1.34 mmol), palladium acetate (28 mg, 0.13 mmol) and tri-o-tolylphosphine (141 mg). The reaction mixture was heated in a sealed tube at 100° C. for 16 h. After cooling to room temperature, saturated NaHCO3 solution was added. The mixture was extracted with EtOAc (2×). The combined organic solvent was dried (MgSO4), concentrated and chromatographed (silica gel; hexane/EtOAc, 2:1 to 1:2) to afford an oil (255 mg, 80%): 1H NMR (CDCl3, 300 Hz) δ 1.50 (s, 9H), 1.90 (m, 1H), 2.00-2.10 (m, 2H), 3.30-3.50 (m, 2H), 4.00 (m, 1H), 4.14-4.24 (m, 2H), 4.28 (m, 1 H), 7.10 (m, 1H), 7.24 (m, 1H), 7.36-7.40 (m, 3H), 8.26 (s, 1H), 8.30 (s, 1H), 8.60 (d, 2H, J=6.5 Hz); MS (CI/NH3) m/z 382 (M+H)+.

Provenance & Evidence