4-Vinylpyridine → HCID 53820685, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (272.0 mg, 1.0 mmol) in acetonitrile (3.0 mL) and triethylamine (2.5 mL) was added 4-vinylpyridine (0.227.0 mL, 2.0 mmol), palladium acetate (23.0 mg, 0.1 mmol) and tri-o-tolylphosphine (122.0 mg). After being heated in a sealed tube at 100° C. overnight, the reaction mixture was cooled to room temperature. A minimum amount of saturated sodium bicarbonate was added to free the amine, and the mixture was extracted with EtOAc, dried (MgSO4), and concentrated. The residue was chromatographed on a silica gel column, eluting with CHCl3 /MeOH 10:1 to afford a light yellowish oil (259 mg, 88%). MS (CI/NH3) m/z 295 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.70-2.13 (m, 3H), 2.27-2.41 (m, 1H), 2.53 (s, 3H), 2.66-2.70 (m, 1H), 3.12-3.20 (m, 1H), 3.97-4.14 (m, 2H), 7.07 (d, J 16.6 Hz, 1H), 7.27 (d, J=16.6 Hz, 1H), 7.38 (d, J=5.5 Hz, 2H), 7.39 (dd, J=2.1 Hz, J=3.0 Hz, 1H), 8.28 (d, J=3.0 Hz, 1H), 8.36 (d, J=2.1 Hz, 1H), 8.62 (d, J=5.5 Hz, 2H).

Provenance & Evidence