反应详情

温度

90 °C

2-Ethoxy-3,5-diisopropyl-phenyl-boronic acid (586 mg, 2.34 mmol) was dissolved in toluene (10 ml). 1-(3-Bromo-thieno[2,3-c]pyridin-5-yl)-ethanone (310 mg, 1.21 mmol), and tetrakis(triphenylphosphine)palladium(0) (140 mg, 0.12 mmol) followed by 2M sodium carbonate solution (2.34 ml) was added to this solution. This mixture was then heated to 90° C. overnight, then poured into brine (20 ml) and extracted with ethyl acetate (2×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The residue was then purified by chromatography (chromatotron, 4μ plate, 10% ethyl acetate in hexanes) to give a 1-[3-(2-ethoxy-3,5-diisopropyl-phenyl)-thieno[2,3-c]pyridin-5-yl]-ethanone as a white solid (422.2 mg, 91%). 1H NMR (250 MHz, CDCl3): δ 9.14 (s, 1H), 8.38 (s, 1H), 7.80 (s, 1H), 7.13 (d, 1H, J=1.9), 6.98 (d, 1H, J=1.9), 3.33 (m, 1H), 3.28 (q, 2H, J=7.5), 2.87 (m, 1H), 2.74 (s, 3H), 1.25 (s, 3H), 1.23 (s, 3H), 1.22 (s, 3H), 1.20 (s, 3H), 0.85 (t, 3H, J=7.5). MS [EI+] 382 (M+H)+.

1. additionwas added to this solution
2. extractionextracted with ethyl acetate (2×20 mL)
3. dry with materialThe organic layers were dried over MgSO4
4. concentrationconcentrated in vacuo
5. customThe residue was then purified by chromatography (chromatotron, 4μ plate, 10% ethyl acetate in hexanes)