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

HRID 42566

Reaktionsgleichung

Reaktionsgleichung von HRID 42566
[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.Cl>COCCO.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:17]=[C:18]3[NH:19][N:20]=[CH:21][C:22]=23)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

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

Produkt 1

HCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridineAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 80192-MethoxyethanolLösungsmittel2×

Versuchsvorschrift

In a volumetric flask, 1-(4-fluorophenyl)-2-(4-pyridyl)ethanone (23.56 g, 109.4 mmol, obtained in reference example 1) and 2-methoxyethanol (150 mL) were introduced. A solution of 3-amino-2H-pyrazole (10.00 g, 120.3 mmol) in 2-methoxyethanol (170 mL) and 37% HCl (3.23 g, 32.8 mmol) were added under argon atmosphere. This was heated to reflux for 3 days. It was allowed to cool and concentrated. The solid obtained was dissolved in CHCl3 (400 mL) and MeOH (50 mL) and washed with 0.1 N HCl (300 mL) and 1 N NaOH (300 mL). The organic phase was dried over Na2SO4 and concentrated to dryness, to afford 9.93 g of the desired product in solid cream form (yield: 47%)

Aufarbeitung

  1. temperatureThis was heated
  2. temperatureto reflux for 3 days
  3. temperatureto cool
  4. concentrationconcentrated
  5. customThe solid obtained
  6. washMeOH (50 mL) and washed with 0.1 N HCl (300 mL) and 1 N NaOH (300 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ad1fdfc90d014991bffdfe53fb8e0465
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536194B2

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