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Isopropanol → 4-(1-Ethyl-6-fluoro-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

HRID 573341
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 573341
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:22](F)=[CH:21][C:20]([F:24])=[CH:19][N:18]=2)=O)=[CH:11][CH:10]=1)C1C=CC=CC=1.[CH2:25]([NH:27][NH2:28])[CH3:26].CC(O)C>O>[CH2:25]([N:27]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([F:24])[CH:21]=2)[C:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[N:28]1)[CH3:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 29062EthylhydrazineHCID 66727888[4-(Benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone

Produkt 1

HCID 1363976944-(1-Ethyl-6-fluoro-1H-pyrazolo[4,3-b]pyridin-3-yl)phenolAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of [4-(benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone (400 mg), ethylhydrazine (369 mg) and 2-propanol (5 mL) was stirred at room temperature for 30 min, and at 90° C. for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in EtOH (40 mL) and 10% Pd—C (50% wet, 400 mg) was added. The mixture was stirred at room temperature for 1 h under H2 atmosphere, filtered and evaporated. The residue was suspended in AcOEt/IPE and collected by filtration to give the title compound (220 mg).

Aufarbeitung

  1. waitat 90° C. for 12 h
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in EtOH (40 mL)
  6. addition10% Pd—C (50% wet, 400 mg) was added
  7. stirringThe mixture was stirred at room temperature for 1 h under H2 atmosphere
  8. filtrationfiltered
  9. customevaporated
  10. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-213f231760d942f5ae48c884aa9b67fe
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029536B2

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