4-Chloro-2-methoxypyridine → (E)-2-Methoxy-4-(2-(pyridin-2-yl)vinyl)pyridine

Participants

Reaction Conditions

Reaction Steps

4-Chloro-2-methoxypyridine (182 mg, 1.27 mmol) and (E)-2-(2-(tributylstannyl)vinyl)pyridine (R. A. Hacck, et al. Tet. Lett 1988, 29, 2783-2786) (500 mg, 1.27 mmol) were stirred in dry toluene (4 mL) and degassed with a nitrogen stream as the temperature was increased to 100° C. Palladium tetrakistriphenylphosphine (146 mg, 0.127 mmol) was added and the reaction mixture was maintained at 100° C. under a nitrogen atmosphere for 16 h. Upon cooling, the mixture was purified by column chromatography (12 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 25 mL/min) to provide the title compound (225 mg, 83%) as a green oil: 1H NMR (500 MHz, CD3OD) δ 8.63 (d, J=4.7 Hz, 1H), 8.15 (d, J=5.4 Hz, 1H), 7.71-7.67 (dt, J=7.5, 1.6 Hz, 1H), 7.53 (d, J=16.4 Hz, 1H), 7.40 (d, J=7.9 Hz, 1H), 7.28 (d, J=16.4 Hz, 1H), 7.22-7.18 (dd, J=7.2, 4.7 Hz, 1H), 7.06 (d, J=5.4 Hz, 1H), 6.85 (s, 1H), 3.96 (s, 3H).

Provenance & Evidence