4-Hydroxybenzaldehyde → 4-[6-(4-Fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]phenol

HRID 42586

Reaktionsgleichung

Reaktionsgleichung von HRID 42586
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[NH:19][N:20]=[CH:21][CH:22]=1.[OH:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.Cl.C([O-])(O)=O.[Na+]>COCCO.C(Cl)(Cl)Cl.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:18]3[NH:19][N:20]=[CH:21][C:22]3=[C:28]([C:27]3[CH:30]=[CH:31][C:24]([OH:23])=[CH:25][CH:26]=3)[C:9]=2[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Komponenten

9

Edukt 5

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 74561Pyrazol-3-ylamineHCID 516892Sodium BicarbonateHCID 103308811-(4-Fluorophenyl)-2-(pyridin-4-yl)ethan-1-one

Produkt 1

HCID 1363678394-[6-(4-Fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]phenolAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 80192-MethoxyethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(4-fluorophenyl)-2-(4-pyridyl)ethanone (0.30 g, 1.4 mmol, obtained in reference example 1) in 2-methoxyethanol (2 mL), 3-amino-2H-pyrazole (0.13 g, 1.5 mmol), 4-hydroxybenzaldehyde (0.17 g, 1.4 mmol), 2-methoxyethanol (2 mL) and 37% HCl (0.04 g, 0.4 mmol) were added under argon atmosphere. The mixture was heated to reflux overnight. It was allowed to cool and concentrated. The solid obtained was dissolved in CHCl3 and some drops of MeOH. Saturated NaHCO3 was added and the aqueous phase was extracted 3 times with CHCl3. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.22 g of the desired compound (yield: 41%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureto cool
  4. concentrationconcentrated
  5. customThe solid obtained
  6. extractionthe aqueous phase was extracted 3 times with CHCl3
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customThe crude product was purified by chromatography on silica gel
  10. temperatureof increasing polarity as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ca35d469f42b472ba26356e3dd442510
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536194B2

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