Ethylene Glycol → HCID 59375126, compound

Participants

Reaction Steps

A mixture of 4-bromo-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide (Intermediate 73-2, 300 mg, 0.864 mmol), p-toluenesulfonic acid monohydrate (8.2 mg, 0.043 mmol) and ethylene glycol (1.45 mL) was stirred at rt overnight. The resulting suspension was treated with NaHCO3 (aq) and diluted with water. The precipitate was collected by filtration, washed with water and dried to provide 4-bromo-7-(2-(2-hydroxyethoxy)propan-2-yl)-9H-carbazole-1-carboxamide as a white solid (324 mg, 96%). 1H NMR (400 MHz, methanol-d4) δ 8.65 (1 H, d, J=8.58 Hz), 7.77 (1 H, d, J=1.10 Hz), 7.75 (1 H, d, J=8.14 Hz), 7.44 (1 H, dd, J=8.36, 1.54 Hz), 7.40 (1 H, d), 3.69 (2 H, t, J=5.17 Hz), 3.32-3.34 (2 H, m), 1.68 (6 H, s). Mass spectrum m/z 413, 415 (M+Na)+.

Provenance & Evidence