Hydrazine → 2-(6-(1H-pyrazolo[3,4-b]pyridin-4-yl)pyridin-2-yl)-2-methylpropanenitrile
Reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([CH3:20])([CH3:19])[C:17]#[N:18])[N:11]=2)[CH:5]=[CH:4][N:3]=1.[NH2:21][NH2:22]>O1CCCC1.C(O)C.O.NN>[NH:21]1[C:2]2=[N:3][CH:4]=[CH:5][C:6]([C:10]3[N:11]=[C:12]([C:16]([CH3:20])([CH3:19])[C:17]#[N:18])[CH:13]=[CH:14][CH:15]=3)=[C:7]2[CH:8]=[N:22]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 2-(2′-chloro-3′-formyl-2,4′-bipyridin-6-yl)-2-methylpropanenitrile (71 mg, 0.25 mmol) and 1M solution of hydrazine in tetrahydrofuran (3 ml) was heated under microwave irradiation at 140° C. for 20 minutes. The mixture was cooled down to room temperature, diluted with ethanol (1 ml) and hydrazine hydrate (1 ml) was added. The reaction mixture was heated under microwave irradiation at 160° C. for 30 minutes. The mixture was cooled down to room temperature, partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified on silica gel by flash column chromatography to afford the title compound as a white solid (14.6 mg, 22% yield).
Workup
- temperatureThe mixture was cooled down to room temperature
- additionwas added
- temperatureThe reaction mixture was heated under microwave irradiation at 160° C. for 30 minutes
- temperatureThe mixture was cooled down to room temperature
- custompartitioned between ethyl acetate and water
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
- customThe residue was purified on silica gel by flash column chromatography
Sources & evidence
- ORD record
- ord-1e0d1dac5a334016833ecf0f906ed54d
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367697B2
Reaction notes
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