1,2-Dichloroethane → 6-bromo-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

Participants

Reaction Steps

To a solution of 6-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid (0.8 g, 2.135 mmol), EDC (0.491 g, 2.56 mmol), and 1-hydroxybenzotriazole hydrate (0.392 g, 2.56 mmol) in THF/CH2Cl2 (5/1) (30 mL) was added morpholine (0.4 mL, 4.27 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated and the solid was washed with ethyl acetate, and water. The organic layer was dried over Na2SO4 and concentrated to afford the crude product as a pale solid. The solid was washed with hexane-ethyl acetate to give 800 mg of pure 6-bromo-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide. MS (ESI) m/z 406 (M+H). 1H NMR (DMSO-d6) δ ppm 10.9 (s, 1H), 8.2 (bs, 1H), 7.81 (d, 1H), 7.75 (s, 1H), 3.92 (m, 4H), 3.77 (q, 2H, J=7.8 Hz), 2.52-2.81 (m, 7H).

Provenance & Evidence