反应详情

2-fluoro-5-formylpyridine (0.55 mmol) and anyhydrous CuCl2 (0.150 g, 1.10 mmol) were added to a solution of 2-amino-N-(4-sec-butylphenyl)benzamide (0.205 g, 0.55 mmol) in anyhydrous EtOH (10 mL). After heating at reflux temperature for 2.5 hours, the mixture was 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 2% to 50% EtOAc in heptane, afforded the title compound as a white solid (15%). 1H-NMR (300 MHz, DMSO-d6): δ 8.17-8.33 (m, 2H), 7.87-8.02 (m, 2H), 7.80 (d, J=8.1 Hz, 1H), 7.62-7.66 (m, 1H), 7.23-7.33 (m, 2H), 7.12-7.22 (m, 2H), 6.98-7.11 (m, 1H), 2.54-2.65 (m, 1H), 1.32-1.66 (m, 2H), 1.15 (d, J=6.9 Hz, 3H), 0.60 (t, J=7.4 Hz, 3H). MS (APCI) m/z: 374 (M+H)+.

1. temperatureAfter heating
2. temperatureat reflux temperature for 2.5 hours
3. concentrationthe mixture was concentrated in vacuo
4. dissolutionThe residue was dissolved in EtOAc
5. washwashed with H2O
6. dry with materialbrine, dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by flash chromatography on silica gel
10. washeluting with 2% to 50% EtOAc in heptane