N-bromobutanimide → HCID 136390253, compound

Participants

Reaction Steps

To a solution of methyl 2-(9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)acetate (0.14 g, 1 eq.) in THF (10 mL) was added N-bromosuccinimide (0.077 g, 1 eq.). The reaction was stirred at room temperature for 30 minutes, poured onto water (30 mL) and extracted with ethyl acetate (2×30 mL). The organic extracts were combined, washed with water (1×50 mL), brine (1×50 mL) and dried over sodium sulfate. After filtration and concentration under reduced pressure, the crude product was purified by column chromatography (2-5% methanol in dichloromethane). The methyl 2-(3-bromo-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)acetate (0.162 g, 98%) was obtained. 1H NMR (DMSO-d6) 400 MHz δ 8.23 (dd, JA=4.4 Hz, JB=1.6 Hz, 1H), 7.96 (dd, JA=7.6 Hz, JB=1.6 Hz, 1H), 7.77 (dd, JA=8.0 Hz, JB=1.6 Hz, 1H), 7.38-7.33 (m, 1H), 7.19 (dd, JA=8.0 Hz, JB=4.8 Hz, 1H), 7.14-7.05 (m, 2H), 3.75 (s, 2H), 3.74 (s, 3H); LCMS: 385, 387 [M+H].

Provenance & Evidence