Sodium Azide → 2-(Azidomethyl)-6-bromopyridine

Participants

Reaction Steps

Sodium azide (3.11 g, 47.8 mmol) and 2-bromo-6-(bromomethyl)pyridine (4.00 g, 15.94 mmol) were combined in DMSO (30 mL) and stirred at room temperature for 4 h. The mixture was subsequently diluted with water and extracted with diethyl ether (2×). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated. The residue was purified by flash chromatography (0-10% EtOAc/hexanes) to yield the title compound as a colorless oil. LRMS (APCI) calc'd for C6H6BrN4 [M+H]+: 213, Found: 213.

Provenance & Evidence