Hydrazine → 2-(6-(1H-pyrazolo[3,4-b]pyridin-4-yl)pyridin-2-yl)-2-methylpropanenitrile

HRID 1920838Notes

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]1

Participants

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-d0e93199cbc242a397579d639851aac8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173635B2

Reaction notes

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