反应详情

9-Benzyl-6-fluoro-9H-carbazol-4-ol (0.0587 g, 0.20 mmol), 2-diethylaminoethylchloride hydrochloride (0.0524 g, 0.30 mmol), potassium carbonate (0.0872 g, 0.63 mmol), sodium iodide (0.0062 g, 0.041 mmol) and DMF (2 mL) are heated at 85° C. for 3 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (50 mL) using methanol/dichloromethane (1/99 to 3/97) to give 0.0485 g (62%) of the title compound; mp 68-69° C.; MS (ESI+) for C25H27FN2O m/z 391.3 (M+H)+; IR (drift) 2966, 1584, 1483, 1463, 1345, 1268, 1185, 1162, 1145, 1052, 799, 778, 741, 726, 713 cm−1; 1H NMR (CDCl3) δ1.14, 2.73, 3.10, 4.33, 5.48, 6.68, 6.97, 7.11, 7.21, 7.35, 8.03. Anal. Calcd for C25H27FN2O: C, 76.89; H, 6.97; N, 7.17. Found: C, 77.16; H, 7.28; N, 7.16.

1. temperatureAfter the mixture had cooled
2. customit is partitioned between water and ethyl acetate
3. dry with materialThe combined organic layers are dried over magnesium sulfate
4. concentrationconcentrated to an oil
5. customThe oil is chromatographed on silica gel (50 mL)