Dimethylformamide → 2-Ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-2H-pyrazolo[4,3-b]pyridine

HRID 572161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572161
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]([CH2:26][CH3:27])[N:19]=[C:20]3[CH:25]=[CH:24][CH:23]=[N:22][C:21]=23)=[CH:13][CH:12]=1.IC.[C:30](=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[CH2:26]([N:18]1[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][C:2]3[N:1]([CH3:30])[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[CH:12][CH:13]=2)=[C:21]2[N:22]=[CH:23][CH:24]=[CH:25][C:20]2=[N:19]1)[CH3:27]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86704970HCID 86704970, Verbindung

Produkt 1

HCID 867049712-Ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-2H-pyrazolo[4,3-b]pyridineAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-[4-(1H-benzimidazol-2-yloxy)phenyl]-2-ethyl-2H-pyrazolo[4,3-b]pyridine (25 mg) obtained in Example 3, iodomethane (5.72 μl), cesium carbonate (34.4 mg) and DMF (1 ml) was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from ethyl acetate/hexane to give the title compound (24.0 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. customrecrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2d4c50df78a84e8199ac31a04b26ac46
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029388B2

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