反应详情

温度

180 °C

To a mixture of sodium chloride (1.23 g, 21.0 mmol) and aluminum chloride (5.0 g, 38.2 mmol) at 130° C. was added 1-(4-bromophenyl)-4-chlorobutan-1-one (1.0 g, 3.82 mmol) and the resulting mixture was heated to 180° C. for 20 minutes. The mixture was allowed to cool to room temperature and poured to a cold 1N aqueous HCl solution (300 mL). The mixture was extracted several times with dichloromethane. The combined organic layers were separated, dried over magnesium sulfate, filtered and concentrated to give 5-bromo-3-methyl-indan-1-one (0.77 g, 89%). The title compound, 1-methyl-5-(3-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile as an orange solid (0.65 g, 76%), was prepared from 5-bromo-3-methyl-indan-1-one and 1-methyl-2-cyanopyrrole according to the same coupling procedure as described in example 1. MS (ES) m/z 251.2; Anal. Calcd for C16H14N2O: C, 76.78; H, 5.64; N, 11.19. Found: C, 76.49; H, 5.49; N, 11.10. HRMS: calcd for C16H14N2O+H+, 251.1179; found (ESI, [M+H]+), 251.1179.

1. temperatureto cool to room temperature
2. extractionThe mixture was extracted several times with dichloromethane
3. customThe combined organic layers were separated
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated