Nitrogen → 3-Chloro-2-(p-tolyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 2,3-dichloropyridine (0.9663 g, 6.5 mmol), p-tolylboronic acid (0.8569 g, 6.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.3618 g, 0.31 mmol) in 0.5 M Na2CO3 (25 mL) and acetonitrile (25 mL) was flushed with N2, sealed and heated at 85° C. for 16 hours. The reaction mixture was cooled to room temperature and the volume reduced by half under vacuum. The concentrate was extracted with dichloromethane (3×20 mL), dried (MgSO4) and condensed to yellow-green oil. The residue was purified by column chromatography, eluted with hexanes:ethyl acetate:dichloromethane (7:2:1)) to provide the title compound as a yellow-orange oil. MS (ESI+) m/z 203 (M+H)+; 1H NMR (DMSO-d6) δ 2.38 (s, 3H), 7.30 (d, J 8.2, 2H), 7.42 (d, J 8.2, 1H), 7.59 (d, J 8.2, 2H), 8.03 (d, J 8.1, 1H), 8.62 (d, J 6.1, 1H); Anal. Calc'd for C12H10ClN.0.1H2O: C, 70.15; H, 5.00; N, 6.82. Found: C, 70.06; H, 4.67; N, 6.67.

Provenance & Evidence