Sodium Iodide → HCID 9953072, compound

Participants

Reaction Steps

9-(4-Fluorobenzyl)-8-methyl-9H-carbazol-4-ol (0.0176 g, 0.058mmol), 2-diethylaminoethylchloride hydrochloride (0.0144 g, 0.084 mmol), potassium carbonate (0.0332 g, 0.24 mmol), sodium iodide (0.0008 g, 0.0053 mmol) and DMF (1 mL) are heated at 85° C. for 4 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The aqueous layer is also washed with dichloromethane. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (10 mL) using methanol/dichloromethane (1/99 and 2/98) to give 0.0148 g (55%) of the title compound; MS (ESI+) for C26H29FN2O m/z 405.2 (M+H)+; 1H NMR (CDCl3) δ1.23, 2.65, 2.88, 3.26, 4.47, 5.75, 6.73, 6.95, 7.15, 7.33, 8.29. Anal. Calcd for C26H29FN2O: C, 77.20; H, 7.22; N, 6.93. Found: C, 73.47; H, 7.06; N, 6.53.

Provenance & Evidence