Hydrazine → HCID 178477865, compound

Temperature

0 °C

(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.

1. temperaturecooled in an ice bath
2. temperatureheated to 70° C. for 1.5 hours
3. customVolatiles were removed under reduced pressure
4. additionTo this mixture was added 20 mL of saturated ammonium chloride and 110 mL of water
5. customThe organic phase was collected
6. washThe combined organic layers were washed with brine
7. dry with materialdried (MgSO4), and solvent
8. customwas removed

ORD record

ord-6886ce78d7fa4affb025d90f19b2a8f7

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566708B2