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

HRID 2376726

Reaktionsgleichung

Reaktionsgleichung von HRID 2376726
[NH2:1][C:2]1[NH:3][N:4]=[CH:5][CH:6]=1.FC1C=CC(C(O[C:15]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=O)=CC=1>CCO.Cl.C(Cl)(Cl)Cl.CO>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:15]2[C:16]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[C:15]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:1]=[C:2]3[NH:3][N:4]=[CH:5][C:6]=23)=[CH:28][CH:27]=1

Komponenten

7

Edukt 2

HCID 74561Pyrazol-3-ylamineHCID 684458621-(4-Fluorophenyl)-2-(4-pyridyl)vinyl 4-fluorobenzoate

Produkt 1

HCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridineAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-2H-pyrazole (60 mg, 71.8 mmol) in EtOH (2 mL) and 1 drop of 37% HCl, 1-(4-fluorophenyl)-2-(4-pyridyl)vinyl 4-fluorobenzoate (0.22 g, 65.0 mmol, obtained in reference example 4) was added under argon atmosphere. This was heated to reflux for 3 days. The mixture was diluted with CHCl3 and MeOH. It was washed with saturated NaHCO3. The aqueous phase was extracted with CHCl3 (×2). The organic phase was 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 58 mg of the desired product in a solid white form (yield: 23%).

Aufarbeitung

  1. temperatureThis was heated
  2. temperatureto reflux for 3 days
  3. washIt was washed with saturated NaHCO3
  4. extractionThe aqueous phase was extracted with CHCl3 (×2)
  5. dry with materialThe organic phase was 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-a57c4f152ad846918e0ddb3c6980ccd6
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468376B2

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