Tert-Butylamine → 8-bromo-N-(tert-butyl)-3-methylquinoxalin-2-amine

Participants

Reaction Steps

A solution of 5-bromo-3-fluoro-2-methylquinoxaline (Example 126f; 1.5 g, 6.22 mmol) and tert-butylamine (Aldrich; 3.27 mL, 31.1 mmol) in DMSO (15 mL) was stirred at 100° C. for 2.5 h. The mixture was subsequently diluted with DCM (150 mL), and washed with saturated aq. NaHCO3 (3×15 mL). The organic layer was separated, dried over MgSO4, filtered, and concentrated. The crude material was purified on a silica gel column (18-25% EtOAc in hexanes) to give 8-bromo-N-(tert-butyl)-3-methylquinoxalin-2-amine (1.58 g, 86% yield) as an amorphous pink solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.79-7.86 (m, 1H), 7.71 (dd, J=8.1, 1.1 Hz, 1H), 7.22 (t, J=7.9 Hz, 1H), 6.17 (s, 1H), 2.55 (s, 3H), 1.58 (s, 9H). m/z (ESI, +ve ion) 294.0/296.0 (M+H)+.

Provenance & Evidence