Water → HCID 89784748, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-2,3-dichloroquinoxaline (LeadGen Labs, LLC, Orange, Conn.) (305 mg, 1.10 mmol) and 2-methylpropan-2-amine (Aldrich) (0.12 mL, 1.10 mmol) in DMSO (5.0 mL) was stirred under argon at 65° C. for 17 h (water-cooled reflux condenser attached to flask). Additional 2-methylpropan-2-amine (0.06 mL, 0.57 mmol) was added, and the resulting solution was stirred at 100° C. for 5 h. The reaction mixture was subsequently cooled to 25° C. and diluted with half-saturated aq. NaHCO3 (80 mL). The resulting mixture was extracted with DCM (2×80 mL), and the combined extracts were sequentially washed with water (2×50 mL), dried over Na2SO4, filtered, and concentrated onto silica gel. Chromatographic purification (silica gel, 0-10% EtOAc/hexanes) furnished a ˜2.5:1 mixture of 8-bromo-N-(tert-butyl)-3-chloroquinoxalin-2-amine and 5-bromo-N-(tert-butyl)-3-chloroquinoxalin-2-amine (224 mg, 0.71 mmol, 65% yield) as an off-white solid: 8-bromo-N-(tert-butyl)-3-chloroquinoxalin-2-amine: 1H NMR (400 MHz, CDCl3) δ ppm 7.86 (1H, dd, J=7.6, 1.0 Hz), 7.72 (1H, dd, J=8.2, 1.0 Hz), 7.21 (1H, t, J=7.9 Hz), 5.63 (1H, br. s.), 1.63 (9H, s). m/z (ESI, +ve) 314.0 (M+H)+. 5-bromo-N-(tert-butyl)-3-chloroquinoxalin-2-amine: 1H NMR (400 MHz, CDCl3) δ ppm 7.65 (1H, d, J=3.7 Hz), 7.63 (1H, d, J=3.3 Hz), 7.39 (1H, t, J=8.0 Hz), 5.60 (1H, br. s.), 1.57 (9H, s). m/z (ESI, +ve) 314.0 (M+H)+.

Provenance & Evidence