2-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridine → (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine

A mixture of 2-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridine (500 mg, 1.79 mmol) and iron powder (767 mg, 13.7 mmol) in EtOH (8 mL) and HOAc (6 mL) was heated at reflux for 2 h. It was filtered through celite. The filtrate was concentrated in vacuo. The residue was partitioned between 5% NaHCO3 and EtOAc. The biphasic solution was filtered. The EtOAc phase was separated, dried over Na2SO4, and concentrated in vacuo to give (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine (253 mg).