Sodium Carbonate → HCID 87071493, compound

Participants

Reaction Conditions

Reaction Steps

Step 1 A mixture of 4-bromo-7-formyl-9H-carbazole-1-carboxamide (prepared according to Step 1 of Example 41-1, 200 mg, 0.631 mmol) and hydroxylamine hydrochloric acid salt (65.7 mg, 0.946 mmol) in ethanol (3 mL) was treated with 2 M aqueous sodium carbonate (0.236 mL, 0.473 mmol) and heated at 80-90° C. After 17.5 h, the mixture was cooled to rt and partitioned between EtOAc and water. The organic phase was dried and concentrated, and the residue was triturated with methanol, and the precipitate was collected by filtration, rinsed with methanol and dried to provide (E)-4-bromo-7-((hydroxyimino)methyl)-9H-carbazole-1-carboxamide as a gray-tan solid (110 mg, 53%). 1H NMR (400 MHz, DMSO-d6) δ 11.87 (1 H, s), 11.33 (1 H, s), 8.65 (1 H, d, J=8.4 Hz), 8.32 (1 H, s), 8.28 (1 H, br. s.), 8.09 (1 H, s), 7.92 (1 H, d, J=8.1 Hz), 7.64 (1 H, br. s.), 7.58 (1 H, d, J=8.6 Hz), 7.51 (1 H, d, J=8.1 Hz). Mass spectrum m/z 332, 334 (M+H)+.

Provenance & Evidence