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

반응식

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

참가 물질

반응물 4

HCID 1049Pyridine

HCID 6342Acetonitrile

HCID 15891Phenyl chloroformate

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

생성물 1

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

실험 절차

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%)