N-bromobutanimide → 3-bromo-2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

Participants

Reaction Steps

To a solution of 2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.7 g, 1 eq.) in THF (20 mL) was added N-bromosuccinimide (0.4 g, 1 eq.). The reaction was stirred at room temperature for 1 hour, poured onto water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic extracts were combined, washed with saturated sodium bicarbonate (1×100 mL), water (1×50 mL), brine (1×50 mL) and dried over sodium sulfate. After filtration and concentration under reduced pressure 3-bromo-2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.85 g, 97%) was obtained which was used with no further purification. 1H NMR (DMSO-d6) 400 MHz δ 8.64 (s, 1H), 8.28 (dd, JA=4.8 Hz, JB=1.6 Hz, 1H), 8.05 (dd, JA=8 Hz, JB=1.6 Hz, 1H), 8.02-7.98 (m, 1H), 7.85 (dd, JA=8 Hz, JB=1.6 Hz, 1H), 7.53-7.48 (m, J=8 Hz, 2H), 7.42-7.34 (m, 2H), 7.30-7.22 (m, 2H), 7.14-7.09 (m, 1H); LCMS: 388 [M+H].

Provenance & Evidence