反应详情

温度

100 °C

A sealable tube containing 6-bromo-3,4-dihydroquinolin-2(1H)-one (0.10 g, 0.44 mmol), 3-pyridylboronic acid (0.56 g, 4.6 mmol), bis(di-tert-butyl(4-dimethylamino phenyl)phosphine)dichloropalladium(II) (6.3 mg, 8.9 μmol), and potassium carbonate (0.18 g, 1.3 mmol) was flushed with nitrogen before tert-butanol (4.9 mL) and water (0.6 mL) were added. The tube was flushed again with nitrogen, sealed tightly and heated to 100° C. overnight. The reaction was then cooled to room temperature, poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic extracts were combined, washed with water, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-15% methanol in ethyl acetate) provided the title compound: LCMS m/z 225.27 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.77 (s, 1H), 8.47 (d, J=4.8 Hz, 1H), 8.06 (ddd, J=1.7, 2.0, 8.1 Hz, 1H), 7.52 (s, 1H), 7.50-7.47 (m, 2H), 6.99 (d, J=8.1 Hz, 1H), 3.05 (t, J=7.5, 7.7 Hz, 2H), 2.61 (t, J=7.5, 7.7 Hz, 2H).

1. customwas flushed with nitrogen before tert-butanol (4.9 mL) and water (0.6 mL)
2. additionwere added
3. customThe tube was flushed again with nitrogen
4. customsealed tightly
5. temperatureThe reaction was then cooled to room temperature
6. additionpoured into saturated aqueous sodium chloride solution
7. extractionextracted with ethyl acetate
8. washwashed with water
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customPurification by flash chromatography on silica gel (0-15% methanol in ethyl acetate)