反应详情

1-(4-Fluorophenyl)-4-(6-(trifluoromethyl)-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indol-8(7H)-yl)-1-butanone (70 mg, 0.15 mmol) and ethylene glycol (10.4 mg, 0.17 mmol) were mixed together in anhydrous toluene (5 mL) in a round bottom flask equipped with a Dean-Stark apparatus and 3 Å molecular sieves. A few crystals of p-TsOH were added and reaction was heated to reflux for 5 hours. The reaction mixture was concentrated under reduced pressure and then extracted with dichloromethane (2×25 mL), washed with saturated sodium carbonate (1×15 mL) and brine (1×15 mL), dried (sodium sulfate) and concentrated. Product was purified by preparative thin layer chromatography on silica gel, and eluted with 10% MeOH in dichloromethane to give the title compound. 1H NMR (CDCl3, 300 MHz): δ8.00-7.95 (m, 2H), 7.10-6.92 (m, 4H), 4.30-4.26 (m, 2H), 4.03-4.00 (m, 1H), 3.79-3.71 (m, 3H), 3.28-3.23 (m, 2H), 2.92-2.82 (m, 5H), 2.73 (t, 2H, J=7.1 Hz), 2.60 (t, 1H, J=7.5 Hz), 2.10-2.05 (m, 2H) ppm.

1. customequipped with a Dean-Stark apparatus and 3 Å molecular sieves
2. customreaction
3. temperaturewas heated
4. temperatureto reflux for 5 hours
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. extractionextracted with dichloromethane (2×25 mL)
7. washwashed with saturated sodium carbonate (1×15 mL) and brine (1×15 mL)
8. dry with materialdried (sodium sulfate)
9. concentrationconcentrated
10. customProduct was purified by preparative thin layer chromatography on silica gel
11. washeluted with 10% MeOH in dichloromethane