N-bromobutanimide → HCID 71730635, compound

Participants

Reaction Steps

A solution of 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (193) (0.30 g, 0.86 mmol) and 1-bromopyrrolidine-2,5-dione (0.23 g, 1.28 mmol) in CHCl3 (8.6 mL) was stirred at RT for 3 h. The reaction mixture was diluted with DCM (150 mL), added to a separatory funnel, and washed with saturated aq. NaHCO3 (3×150 mL); the organic layer was separated, dried over Na2SO4, and concentrated. The crude product was directly injected onto the column and was purified via automated flash chromatography (silica gel) with 1-4% of 2 M NH3 in MeOH/DCM to give 3-bromo-2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (349) (228 mg, 0.53 mmol, 62% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.60 (s, 9H) 2.55 (s, 3H) 2.97 (t, J=6.85 Hz, 2H) 3.61 (td, J=6.85, 2.74 Hz, 2H) 4.85 (s, 1H) 5.51 (br. s., 1H) 7.44 (t, J=7.92 Hz, 1H) 7.74 (dd, J=8.02, 1.37 Hz, 1H) 8.71 (dd, J=7.63, 1.37 Hz, 1H) 12.28 (br. s., 1H). MS (ESI, pos. ion) m/z: 428.0/430.1 (M+1).

Provenance & Evidence