反应详情

温度

80 °C

Potassium acetate (54.3 g, 44 mmol), pinacol diboron (5.5 g, 22 mmol) and PdCl2(dppf) (0.60 mg, 0.73 mmol) were added sequentially to a solution 1-(4-methoxybenzyl)-6-bromoquinolin-2(1H)-one (5.0 g, 15 mmol) in DMF (70 mL). After flushing with N2, the reaction vessel was sealed and heated at 80° C. for 14 h and then partitioned between H2O and EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) concentrated and purified via column chromatography to yield 1-(4-methoxybenzyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-one (38 g, 67% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.04 (brs, 1H), 7.86 (dd, J=1.2, and 8.4 Hz, 1H), 7.76 (d, J=9.6 Hz, 1H), 7.32 (d, J=9.2 Hz, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 6.80 (d, J=9.6 Hz, 1H), 5.52 (brs, 2H), 3.77 (s, 3H), 1.36 (s, 12H); LC-MS (EI) m/z: 392.3 (M+H+).

1. customAfter flushing with N2
2. customthe reaction vessel was sealed
3. custompartitioned between H2O and EtOAc
4. washThe combined organic extracts were washed with brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. custompurified via column chromatography