反应详情

温度

80 °C

A mixture of 6-bromo-2-isopropenylquinoline (200 mg, 1.45 mmol), palladium acetate (18.1 mg, 0.081 mmol), 1,3-bis(diphenylphosphino)propane (33 mg, 0.081 mmol), triethylamine (245 mg, 2.42 mmol. 0.337 ml) and methanol (1.03 g, 1.31 ml 32.2 mmol) in dry DMF (2.5 ml) was heated at 80° C. under carbon monoxide gas (balloon) overnight (15 hours). The mixture was diluted with ethyl acetate-toluene (8:1) (159 ml) and the precipitate was filtered through a pad of celite. The organic layer was washed with water (×2), brine, dried over sodium sulfate and concentrated in vacuo to give the crude product. The crude product was purified by column chromatography on silica gel (150 g) with hexane-ethyl acetate (15:1) to furnish the title compound (150 mg, 82%) as dark yellow solid. 1H NMR (270 MHz, CDCl3) δ 2.36 (3H, s), 3.99 (3H, s), 5.53-5.57 (1H, m), 5.98 (1H, s), 7.73-7.78 (1H, m), 8.08-8.31 (3H, m), 8.54-8.56 (1H, m). MS (ESI): m/z 228.21 [M+H]+.

1. filtrationthe precipitate was filtered through a pad of celite
2. washThe organic layer was washed with water (×2), brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customto give the crude product
6. customThe crude product was purified by column chromatography on silica gel (150 g) with hexane-ethyl acetate (15:1)