Water → 5-Azido-5,6,7,8-tetrahydroquinoxaline

Participants

Reaction Conditions

Reaction Steps

5-bromo-5,6,7,8-tetrahydroquinoxaline, (Intermediate 20) (3.8 g, 17.92 mmol) and sodium azide (2.3 g, 35.8 mmol) were dissolved in DMF (50 mL) under nitrogen atmosphere and the reaction mixture was warmed to 60° C. for 20 hours. The mixture was cooled to room temperature and poured over water (200 mL), and was extracted with CH2Cl2 (3×100 mL). The organic extracts were washed with brine (2 ×100 mL), dried and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel using 1:1 EtOAc/hexanes to afford 5-azido-5,6,7,8-tetrahydroquinoxaline, (Intermediate 21) (3.2 g, 84%).

Provenance & Evidence