Methanol → HCID 59375101, compound

Participants

Reaction Steps

A solution of ethyl 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazole-2-carboxylate (Example 3-12, 0.81 g, 2.152 mmol) in THF (26.9 mL) at 0° C. was treated with lithium aluminum hydride (1.0 M in THF, 3.01 mL, 3.01 mmol), and the mixture was stirred at rt for 5 h. Additional lithium aluminum hydride (1.3 mL, 1.3 mmol) was added and the mixture was stirred at rt overnight. The mixture was treated with methanol and TFA and diluted with EtOAc, washed with brine, dried and concentrated to provide impure 4-(2-fluorophenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide (0.78 g) contaminated with starting material. A small amount was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide, isolated as the TFA salt. 1H NMR (500 MHz, methanol-d4) δ 7.82 (1 H, d, J=7.8 Hz), 7.51 (1 H, s), 7.44-7.50 (1 H, m), 7.42 (1 H, td, J=7.5, 1.9 Hz), 7.25-7.30 (1 H, m), 7.22 (1 H, t, J=9.2 Hz), 7.05 (1 H, d, J=8.3 Hz), 6.99 (1 H, d, J=7.8 Hz), 6.85 (1 H, dd, J=8.0, 1.4 Hz), 4.62 (2 H, s). Mass spectrum m/z 334.9 (M+H)+.

Provenance & Evidence