Methanol → (5-Bromo-3-(tert-butylamino)quinoxalin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-3-(tert-butylamino)quinoxaline-2-carbaldehyde (306a) (113 mg, 0.37 mmol) and sodium triacetoxyhydroborate (78 mg, 0.37 mmol) in THF (7.5 mL) was stirred at 25° C. for 10 min. MeOH (1.0 mL) was added, and the resulting mixture was stirred at 25° C. for 10 min. Additional sodium triacetoxyhydroborate (78 mg, 0.37 mmol) was added, and the resulting mixture was stirred at 25° C. for 10 min. Further sodium triacetoxyhydroborate (78 mg, 0.37 mmol) was added, and the resulting mixture was stirred at 25° C. for 10 min. Saturated aq. NaHCO3 (10 mL) was then added, and the resulting mixture was partitioned between EtOAc (70 mL) and half-saturated aq. NaHCO3 solution (50 mL). The organic layer was separated, and the aq. layer was extracted with EtOAc (30 mL). The combined organic extracts were washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated in vacuo to provide (5-bromo-3-(tert-butylamino)quinoxalin-2-yl)methanol (114 mg, 0.37 mmol, 100% yield) as a yellow-brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (1H, d, J=7.6 Hz), 7.76 (1H, d, J=8.0 Hz), 7.20 (1H, t, J=7.9 Hz), 5.10 (1H, br. s.), 4.72 (2H, s), 3.92 (1H, br. s.), 1.62 (9H, s). m/z (ESI, +ve) 310.0/312.0 (M+H)+.

Provenance & Evidence