2-Chloroethyl isocyanate → 4-bromo-7-(2-oxoimidazolidin-1-yl)-9H-carbazole-1-carboxamide

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Reaction Steps

A solution of 7-amino-4-bromo-9H-carbazole-1-carboxamide hydrobromide (Example 54-2, 700 mg, 1.818 mmol) and DIEA (0.381 mL, 2.182 mmol) in DMF (5 mL) was treated with 1-chloro-2-isocyanatoethane (230 mg, 2.182 mmol). After 2 h, the mixture was treated with NaH (60% in mineral oil, 582 mg, 14.54 mmol). After 10 min, the mixture was diluted with water. The precipitate was collected by filtration, dried, triturated with methanol, collected again by filtration and dried to provide 4-bromo-7-(2-oxoimidazolidin-1-yl)-9H-carbazole-1-carboxamide as a light yellow solid (410 mg, 60%). 1H NMR (400 MHz, DMSO-d6) δ 11.55 (1 H, s), 8.46 (1 H, d, J=8.80 Hz), 8.16 (1 H, br. s.), 7.92 (1 H, s), 7.77 (1 H, d, J=8.14 Hz), 7.63-7.68 (1 H, m), 7.52 (1 H, br. s.), 7.36-7.41 (1 H, m), 6.99 (1 H, s), 3.92-3.98 (2 H, m), 3.43-3.50 (2 H, m). Mass spectrum m/z 373, 375 (M+H)+.

Provenance & Evidence