N-bromobutanimide → 9-Bromo-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7h)-one

Participants

Reaction Steps

To a solution of Example 1D (1.54 g, 6.07 mmol) in acetic acid/water (1:1, 20 mL) was added N-bromosuccinimide (1.08 g, 6.07 mmol). The reaction mixture was stirred at room temperature for 2 hours. Product precipitated. The precipitate was collected to afford the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 7.36 (d, J=8.54 Hz, 1 H), 7.16 (s, 1 H), 7.11 (d, J=8.85 Hz, 1 H), 3.54-3.63 (m, 1 H), 3.22-3.40 (m, 4 H), 2.93-3.07 (m, 2 H), 2.65-2.72 (m, 1 H), 2.08 (d, J=13.73 Hz, 1 H); MS (ESI) m/z 297.8 (M+H)+.

Provenance & Evidence