Pyridine → phenyl 1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate

Reaktionsgleichung

C[N:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([N+:11]([O-])=O)[C:3]1=O.[N:15]1[CH:20]=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23].C(#[N:33])C>>[NH:33]1[C:7]2=[N:2][CH:3]=[C:4]([NH:11][C:22](=[O:23])[O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:5]=[C:6]2[CH:20]=[N:15]1

Komponenten

Edukt 4

HCID 1049Pyridine

HCID 6342Acetonitrile

HCID 15891Phenyl chloroformate

HCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Produkt 1

HCID 86676322phenyl 1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate

Versuchsvorschrift

1H-Pyrazolo[3,4-b]pyridin-5-amine (B) (212 mg, 1.58 mmol) was dissolved in acetonitrile. To the reaction mixture was added pyridine (0.15 mL, 1.896 mmol) and phenyl chloroformate (0.2 mL, 1.659 mmol) and stirred at room temperature for 30 min under N2. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude was purified by column chromatography to give phenyl 1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate (C). (285 mg, 71%)