Acetic Acid → HCID 77230551, compound

Participants

Reaction Conditions

Reaction Steps

Sodium azide (241.6 mg, 3.72 mmol) and triethyl orthoformate (1.0 mL, 6.01 mmol) were added to a stirred solution of 5-amino-2-bromopyridine (511.8 mg, 2.96 mmol) in acetic acid (3 mL, 52.4 mmol), and the reaction mixture was heated to 80° C. After 7 hours, the reaction mixture was cooled to room temperature before being evaporated under reduced pressure. The resulting red/brown solid was partitioned between EtOAc (50 mL) and water (50 mL). The aqueous layer was extracted with EtOAc (2×50 mL). The organic layers were combined, washed with 1 N HCl (2×50 mL), saturated aqueous NaHCO3 (1×50 mL), and brine (1×50 mL), dried over Na2SO4, filtered, and evaporated under reduced pressure to give an amber solid. Flash chromatography of the solid utilizing an 40 g silica RediSep Rf® column and employing a 0-2% MeOH/DCM gradient with a 2% MeOH/DCM hold afforded the title compound as a light yellow solid. LC-MS: calculated for C6H4BrN5 224.97, 226.96 observed m/e: 226.22, 228.21 (M+H)+ (Rt 0.42/2 min).

Provenance & Evidence