Hydrazine → HCID 178477865, compound

Participants

Reaction Conditions

Reaction Steps

(2-Chloro-phenyl)-(2,6-dichloro-pyridin-3-yl)-methanone (3.0 g, 10.47 mmol) was dissolved in 25 mL of ethanol/THF (4:1) and cooled in an ice bath. Hunig's base (N,N-diisopropylethylamine, 1.8 mL, 10.47 mmol) was added to the reaction mixture, followed by dropwise addition of 0.36 mL (11.52 mmol) of hydrazine. The reaction mixture was stirred at 0° C. for five minutes, then heated to 70° C. for 1.5 hours. Volatiles were removed under reduced pressure, and the residue was taken up in 150 mL of EtOAc, 10 mL of THF and 10 mL of MeOH. To this mixture was added 20 mL of saturated ammonium chloride and 110 mL of water. The organic phase was collected, and the aqueous phase was wahsed with an additional 100 mL of EtOAc. The combined organic layers were washed with brine, dried (MgSO4), and solvent was removed to to yield 1.18 g of 6-chloro-3-(2-chloro-phenyl)-1H-pyrazolo[3,4-b]pyridine as a yellow solid. Mass Spec. M−H=262.

Provenance & Evidence