反应详情

温度

70 °C

To a flask containing 1,1-dimethylethyl 4-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate (3.80 g, 11.5 mmol, prepared according to Heterocycles, 1996, 43, 2131-2138) were added the title compound from Example 3 Step A (3.80 g, 13.8 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (804 mg, 1.15 mmol). Acetonitrile (57 mL) and sodium carbonate (28.7 mL, 1.0 M aqueous, 28.7 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 3 h, then was allowed to cool to ambient temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 10% EtOAc in hexanes, then 10 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 276.0 [M-C4H9]+; 1H NMR (500 MHz, CDCl3) δ 7.89 (d, J=9.0 Hz, 1H), 7.24-7.22 (m, 2H), 6.12 (br s, 1H), 4.09 (br m, 2H), 3.88 (s, 3H), 3.65-3.62 (m, 2H), 2.61 (s, 3H), 2.52 (br m, 2H), 1.49 (s, 9H).

1. customthe resulting mixture was degassed via nitrogen
2. customsparge
3. temperatureto cool to ambient temperature
4. additionwas poured into water
5. extractionThe mixture was extracted with EtOAc
6. concentrationthe organic phase was concentrated in vacuo
7. customPurification by chromatography on silica gel (0 to 10% EtOAc in hexanes