1,2-Dichloroethane → HCID 59375131, compound

Participants

Reaction Steps

A mixture of 5-bromo-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid (Intermediate 46-3, 70% purity, mixed with Intermediate 47-3 from an incomplete reaction done according to the procedure used to prepare Intermediate 47-1; 3 g, 7.14 mmol) in THF (80 mL) and DCM (20 mL) was treated with HOAT (1.166 g, 8.57 mmol) and EDC (1.642 g, 8.57 mmol). The mixture was stirred at rt for 2.5 h, then was treated with anhydrous ammonia gas for ca. 2 min, forming a very thick slurry. The mixture was stirred for 30 min, then was treated again with ammonia gas for ca. 1 min. After stirring for another hour, the mixture was diluted with water and EtOAc (dissolving the solid). The layers were separated and the aqueous phase was extracted again with EtOAc. The combined organic layers were washed twice with 0.1 M aqueous sodium hydroxide, then with 1 M hydrochloric acid and brine, dried and concentrated to provide 5-bromo-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a pale orange-tan solid (2.47 g, 84%, including the product from the incomplete reaction yielding the starting material). 1H NMR (400 MHz, DMSO-d6) δ 10.95 (1H, s), 8.02 (1H, br. s.), 7.44 (1H, d, J=7.9 Hz), 7.38 (1H, br. s.), 7.14 (1H, d, J=8.1 Hz), 2.99 (2H, br. s.), 2.75 (2H, br. s.), 1.78 (4H, br. s.). Mass spectrum m/z 293, 295 (M+H)+.

Provenance & Evidence