반응 #70907

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3-amino-6-(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

3-Amino-6-(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

isonicotinoyl chloride hydrochloride

→

title compound

수율 68.0%

N-[6-(4-Fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]isonicotinamide

수율 68.0%

용매

pyridine

반응 조건

후처리

1. 1
   workup.ADDITIONwere introduced under argon atmosphere
2. 2
   농축It was concentrated
3. 3
   workup.DISSOLUTIONthe residue dissolved in a mixture of CHCl3 and 1 N HCl
4. 4
   기타The phases were separated
5. 5
   추출the aqueous phase was extracted with CHCl3 (×2)
6. 6
   workup.ADDITIONThe aqueous phase was basified by slow addition of 1 N NaOH
7. 7
   workup.ADDITIONBrine was added
8. 8
   추출extracted with CHCl3 and EtOAc
9. 9
   건조The organic phase was dried over Na2SO4
10. 10
    농축concentrated to dryness
11. 11
    기타The crude product obtained
12. 12
    기타was purified by chromatography on silica gel
13. 13
    온도of increasing polarity as eluent

실험 절차

In a volumetric flask, 3-amino-6-(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.20 g, 0.7 mmol, obtained in example 70), isonicotinoyl chloride hydrochloride (0.12 g, 0.7 mmol, obtained in section a) and pyridine (1 mL) were introduced under argon atmosphere. This was stirred at room temperature for 2 days. It was concentrated and the residue dissolved in a mixture of CHCl3 and 1 N HCl. The phases were separated and the aqueous phase was extracted with CHCl3 (×2). The aqueous phase was basified by slow addition of 1 N NaOH. Brine was added and extracted with CHCl3 and EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using CHCl3-MeOH mixtures of increasing polarity as eluent, to afford 98 mg of the title compound (yield: 68%).

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