Water → 4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide

HRID 2376743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2376743
[OH-].[K+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[N:13]=[C:12]3[NH:29][N:30]=[C:31]([C:32]#[N:33])[C:11]=23)=[CH:6][CH:5]=1.O.CC[O:37]C(C)=O>CC(O)(C)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[N:13]=[C:12]3[NH:29][N:30]=[C:31]([C:32]([NH2:33])=[O:37])[C:11]=23)=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 178510687HCID 178510687, Verbindung

Produkt 1

HCID 1785138434,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A solution of KOH (0.07 g, 1.3 mmol) in tBuOH (2.5 mL) was added under argon atmosphere to 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (0.05 g, 0.1 mmol, obtained in example 65) and heated to reflux overnight. Water and EtOAc were added and the phases were separated. The aqueous phase was extracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 15 mg of the title compound in solid form (yield: 28%)

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe crude product obtained
  8. customwas purified by chromatography on silica gel
  9. temperatureof increasing polarity as eluent

Quellen und Nachweise

ORD-Eintrag
ord-5130d01e09ca482f8a8c8a86e87a4842
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468376B2

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