反应详情

温度

90 °C

4-Bromo-2-methoxypyridine (1.85 g, 9.84 mmol), (E)-phenylvinylboronic acid (4.3 g, 30 mmol), K2CO3 (4.0 g, 30 mmol) and [1,1′-Bis-(diphosphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2dppf) (400 mg, 0.5 mmol) were stirred in DMSO (15 mL) under vacuum for 30 min. The flask was flushed with nitrogen and the mixture was heated at 90° C. for 30 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried, concentrated, and the residue was purified by column chromatography (silica gel, hexanes/ethyl acetate, 97:3 to 75:25) to provide the title compound (1.93 g, 93%) as an orange oil: 1H NMR (300 MHz, CDCl3) δ 8.12 (d, J=5.2 Hz, 1H), 7.51 (m, 2H), 7.40-7.22 (m, 4H), 7.02-6.94 (m, 2H), 6.78 (s, 1H), 3.95 (s, 3H).

1. customThe flask was flushed with nitrogen
2. temperatureUpon cooling
3. additionthe mixture was diluted with methylene chloride
4. washwashed with 5% lithium chloride solution (5×)
5. customdried
6. concentrationconcentrated
7. customthe residue was purified by column chromatography (silica gel, hexanes/ethyl acetate, 97:3 to 75:25)