Methanesulfonyl chloride → HCID 86642950, compound

Participants

Reaction Steps

Step 1 A suspension of 4-bromo-7-(hydroxymethyl)-9H-carbazole-1-carboxamide (Example 30-2, 300 mg, 0.940 mmol) and TEA (0.262 mL, 1.880 mmol) in THF (9.4 mL) was treated dropwise with methanesulfonyl chloride (0.077 mL, 0.987 mmol) and the mixture was stirred at rt for 1 hr. It was treated with NaHCO3 (aq) and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated to provide crude (5-bromo-8-carbamoyl-9H-carbazol-2-yl)methyl methanesulfonate as a light yellow solid (390 mg, 89%). This material was suspended in DMF (8.3 mL) and treated with sodium azide (271 mg, 4.17 mmol). After being stirred overnight at rt, the mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated to provide crude 7-(azidomethyl)-4-bromo-9H-carbazole-1-carboxamide as a light yellow solid (350 mg, 97%). 1H NMR (400 MHz, DMSO-d6) δ 11.80 (1 H, s), 8.62 (1 H, d, J=8.4 Hz), 8.22 (1 H, br. s.), 7.88 (1 H, d, J=8.1 Hz), 7.83 (1 H, s), 7.58 (1 H, br. s.), 7.46 (1 H, d, J=8.4 Hz), 7.28 (1 H, dd, J=8.1, 1.5 Hz), 4.63 (2 H, s).

Provenance & Evidence