Water → 7-(aminomethyl)-4-bromo-9H-carbazole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

Step 2 A mixture of 7-(azidomethyl)-4-bromo-9H-carbazole-1-carboxamide (350 mg, 0.814 mmol), triphenylphosphine (427 mg, 1.627 mmol), and water (18 μL, 0.976 mmol) in THF (10 mL) was heated at 70° C. for 3.5 h. The mixture was cooled to rt and partitioned between EtOAc and 1 M hydrochloric acid. The pH of the aqueous phase was raised to 8-9 with sodium hydroxide pellets, and then was extracted with EtOAc. The organic phase was dried and concentrated to provide crude 7-(aminomethyl)-4-bromo-9H-carbazole-1-carboxamide as a yellow glassy foam (320 mg, 99%). 1H NMR (400 MHz, DMSO-d6) δ 11.61 (1 H, br.), 8.47-8.55 (1 H, m), 8.19 (1 H, br. s.), 7.81-7.84 (1 H, m), 7.76 (1 H, s), 7.63-7.66 (1 H, m), 7.53-7.59 (2 H, m), 7.41 (1 H, d, J=8.1 Hz), 7.27 (1 H, dd, J=8.4, 1.3 Hz), 3.90 (2 H, s).

Provenance & Evidence