反应详情

温度

80 °C

To a mixture of 6-chloro-2-isopropoxy-nicotinonitrile (0.73 g, 4.0 mmol) and 3H-Benzo[c][1,2]oxaborole-1,5-diol (0.40 g, 2.66 mmol) in DMF (10 mL) was added potassium carbonate (1.10 g, 7.98 mmol). The resulting suspension was heated at 80° C. overnight. DMF was removed under reduced pressure, the residue was diluted with EtOAc (50 mL), washed with water (10 mL) and brine (2×10 mL), dried over Na2SO4, filtered, and concentrated to give brown oil. Purification was accomplished by reverse phase preparative HPLC using MeOH/H2O (0.1% AcOH) as the eluent to yield the title compound (0.21 g, 21%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.27 (s, 1 H), 8.23 (d, J=8.6 Hz, 1 H), 7.79 (d, J=7.8 Hz, 1H), 7.29 (s, 1 H), 7.22-7.14 (m, 1 H), 6.70 (d, J=8.2 Hz, 1 H), 4.99 (s, 2 H), 4.85 (sept., J=6.3 Hz, 1 H), 1.19 (d, J=6.3 Hz, 6 H); MS (ES) m/z: 311 (M+1)+; HPLC purity 98.44% (Maxplot), 97.99% (220 nm).

1. customDMF was removed under reduced pressure
2. additionthe residue was diluted with EtOAc (50 mL)
3. washwashed with water (10 mL) and brine (2×10 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give brown oil
8. customPurification