Hydrochloric Acid → HCID 59375149, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of ethyl 8-carbamoyl-5-(3-(4-fluorobenzamido)-2-methylphenyl)-9H-carbazole-2-carboxylate (Intermediate 3-100, 1.63 g, 3.20 mmol) in ethanol (12 mL) was treated with 1 M aqueous sodium hydroxide (1.5 mL, 1.500 mmol), forming a yellow suspension which was heated at 90-95° C. for 30 min. The mixture was cooled to rt and acidified with 1 M hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to provide 8-carbamoyl-5-(3-(4-fluorobenzamido)-2-methylphenyl)-9H-carbazole-2-carboxylic acid as an off-white solid (1.496 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 12.76 (br. s., 1H) 11.84 (s, 1H) 10.15 (s, 1H) 8.38 (s, 1H) 8.24 (br. s., 1H) 8.03-8.13 (m, 3H) 7.56 (br. s., 1H) 7.46-7.54 (m, 2H) 7.42 (t, J=7.7 Hz, 1H) 7.35 (t, J=9.0 Hz, 2H) 7.23 (dd, J=7.5, 1.3 Hz, 1H) 7.04 (d, J=7.5 Hz, 1H) 7.01 (d, J=8.3 Hz, 1H) 1.88 (s, 3H). Mass spectrum m/z 482.1 (M+H)+.

Provenance & Evidence