Sodium Iodide → N,N-Diethyl-N-(2-{[6-fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-yl]oxy}ethyl)amine

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Reaction Steps

6-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol (0.0584 g, 0.19 mmol), 2-diethylaminoethylchloride hydrochloride (0.0593 g, 0.35 mmol), potassium carbonate (0.0926 g, 0.63 mmol), sodium iodide (0.0061 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 give 0.0471 g (61%) of the title compound; mp 75-76° C.; MS (ESI+) for C25H26F2N2O m/z 409.3 (M+H)+; IR (drift) 1585, 1507, 1481, 1461, 1343, 1269, 1221, 1159, 1145, 871, 820, 799, 776, 739, 712 cm−1; 1H NMR (CDCl3) δ1.14, 2.73, 3.10, 4.33, 5.44, 6.69, 6.93, 7.04-7.18, 7.36, 8.03. Anal. Calcd for C25H26F2N2O: C, 73.51; H, 6.41; N, 6.86. Found:C, 73.30; H, 6.59; N, 6.77.

Provenance & Evidence