反应详情

温度

150 °C

6-Methoxy-3-pyridinecarboxaldehyde (1.20 mmol), NaHSO3 (0.200 g, 1.90 mmol) and p-TsOH (0.024 g, 0.12 mmol) were added to a solution of 2-amino-N-(4-sec-butylphenyl)benzamide (0.340 g, 1.20 mmol) in DMA (10 mL). The mixture was heated and stirred at 150° C. overnight and concentrated in vacuo. The residue was dissolved in EtOAc, and washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 15% to 100% EtOAc in heptane, afforded the title compound as a white solid (26%). 1H-NMR (300 MHz, DMSO-d6): δ 8.11-8.27 (m, 2H), 7.89-7.91 (m, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.51-7.67 (m, 2H), 7.11-7.33 (m, 4H), 6.62 (d, J=8.0 Hz, 1H), 3.77 (s, 3H), 2.54-2.68 (m, 1H), 1.30-1.71 (m, 2H), 1.16 (d, J=7.0 Hz, 3H), 0.64 (t, J=7.4 Hz, 3H). MS (APCI) m/z: 386 (M+H)+.

1. temperatureThe mixture was heated
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in EtOAc
4. washwashed with H2O
5. dry with materialbrine, dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customPurification by flash chromatography on silica gel
9. washeluting with 15% to 100% EtOAc in heptane