Dimethylformamide → 2-(Azidomethyl)-5-chloro-3-(2-(trifluoromethyl)phenyl)quinoxaline

Participants

Reaction Steps

To a stirring solution of 2-(bromomethyl)-5-chloro-3-(2-(trifluoromethyl)phenyl)-quinoxaline (0.7173 g, 1.786 mmol) in DMF (8.930 mL, 1.786 mmol) was added sodium azide (0.2322 g, 3.572 mmol) at room temperature and the mixture was stirred at room temperature. After 30 min, the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The organic layer was washed with brine (50 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure to give bluish-brown syrup. The bluish-brown syrup was purified by silica gel column chromatography on a 40 g of Redi-Sep™ column using 0 to 50% gradient of EtOAc in hexane over 14 min, then 50% isocratic of EtOAc for 5 min as eluent to give 2-(azidomethyl)-5-chloro-3-(2-(trifluoromethyl)phenyl)quinoxaline: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.20 (1 H, dd, J=8.6, 1.2 Hz), 8.10-8.14 (1 H, m), 7.99 (1 H, d, J=7.8 Hz), 7.95 (1 H, dd, J=8.4, 7.6 Hz), 7.79-7.91 (3 H, m), 4.41-4.67 (2 H, m); LC-MS (ESI) major peak of m/z 364.0 [M+H]+. The crude product was carried on crude without purification for the next step.

Provenance & Evidence