Methanesulfonyl chloride → HCID 86642949, compound

Participants

Reaction Steps

A solution of 4-(2-fluorophenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide (Example 30-1, 223 mg, 0.667 mmol) and TEA (0.279 mL, 2.001 mmol) in THF (8 mL) was treated with methanesulfonyl chloride (0.104 mL, 1.334 mmol). The resulting suspension was stirred at rt for 15 min. The mixture was diluted with EtOAc, washed with water and brine, and dried and concentrated to provide crude (8-carbamoyl-5-(2-fluorophenyl)-9H-carbazol-2-yl)methyl methanesulfonate as a yellow glassy foam (300 mg, ca. 50% purity). A portion of this material (80 mg, 0.097 mmol) was dissolved in DMF (1 mL), treated with morpholine (84 mg, 0.970 mmol) and heated at 45° C. for 3 days. The mixture was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-(morpholinomethyl)-9H-carbazole-1-carboxamide (9.6 mg, 23%). 1H NMR (400 MHz, methanol-d4) δ 7.94 (1H, d, J=7.8 Hz), 7.59 (1H, s), 7.52-7.58 (1H, m), 7.48-7.52 (1H, m), 7.33-7.39 (1H, m), 7.30 (1H, t, J=9.0 Hz), 7.21 (1H, d, J=8.3 Hz), 7.14 (1H, d, J=7.8 Hz), 6.99 (1H, dd, J=8.3, 1.5 Hz), 3.81 (2H, s), 3.71-3.77 (4H, m), 2.66 (4H, br. s.). Mass spectrum m/z 404.2 (M+H)+.

Provenance & Evidence