Water → methyl 6-(1H-pyrazol-1-yl)nicotinate

HRID 1009919

Reaktionsgleichung

Reaktionsgleichung von HRID 1009919
[NH:1]1[CH:5]=[CH:4][CH:3]=C1.[H-].[Na+].Cl[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1.O.C[N:21](C=O)C>>[N:1]1([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=2)[CH:5]=[CH:4][CH:3]=[N:21]1

Komponenten

6

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 8027PyrroleHCID 24758Sodium hydrideHCID 254249Methyl 6-chloropyridine-3-carboxylate

Produkt 1

HCID 3741563methyl 6-(1H-pyrazol-1-yl)nicotinateAusbeute 64 %

Versuchsvorschrift

To a suspension of pyrrole (0.356 g, 5.23 mmol) in DMF (20 ml) was added sodium hydride (60% in oil, 0.233 g, 5.81 mmol). After stirring for 5 hrs., methyl 6-chloronicotinate (1.00 g, 5.81 mmol) was added, and the mixture was further stirred for 27 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried (over anhydrous MgSO4). After concentration under reduced pressure, the precipitated solid was collected by filtration and washed with hexane to give the title compound (0.683 g, 64%) as a colorless powder.

Aufarbeitung

  1. stirringthe mixture was further stirred for 27 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried (over anhydrous MgSO4)
  5. concentrationAfter concentration under reduced pressure
  6. filtrationthe precipitated solid was collected by filtration
  7. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-aa8c175cd710439180fe9316dc9635d3
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973163B2

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