Hydrazine, ethyl-, ethanedioate (1:1) → HCID 117992935, compound

Participants

Reaction Steps

To a solution of 4-bromo-2,6-difluorobenzaldehyde (1000 mg, 4.5 mmol) in NMP (10 mL) was added ethyl hydrazine oxalate (747 mg, 5.0 mmol). The reaction mixture was stirred at r.t. for 72 h. The reaction mixture was heated under reflux for 15 h. After being cooled at r.t., the reaction mixture was partitioned between heptane and water. The aqueous layer was extracted with heptane. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0-20% EtOAc in heptanes) to afford 6-bromo-1-ethyl-4-fluoro-1H-indazole as a light yellow oil (902 mg, 84%).

Provenance & Evidence