Water → 3-methyl-5-nitro-2-(1H-pyrazol-1-yl)pyridine

HRID 340487

Reaktionsgleichung

Reaktionsgleichung von HRID 340487
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH:11]=[CH:10][CH:9]=[N:8]1.CN(C)C(=[O:16])C.Cl[C:19]1[N:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=1[CH3:26].[OH2:27]>>[CH3:26][C:20]1[C:19]([N:7]2[CH:11]=[CH:10][CH:9]=[N:8]2)=[N:24][CH:23]=[C:22]([N+:25]([O-:16])=[O:27])[CH:21]=1

Komponenten

6

Edukt 5

HCID 962WaterHCID 1048PyrazoleHCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 122956076-Chloro-5-methylpyridin-3-amine

Produkt 1

HCID 638116363-methyl-5-nitro-2-(1H-pyrazol-1-yl)pyridine

Versuchsvorschrift

Cesium carbonate (75 mg) and pyrazole (12 mg) were added to an N,N-dimethylacetamide (5 ml) solution containing 6-chloro-5-methylpyridin-3-amine (12 mg), followed by reflux for 3.5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 10:1), and a light yellow solid of 3-methyl-5-nitro-2-(1H-pyrazol-1-yl)pyridine (12 mg) was obtained.

Aufarbeitung

  1. temperatureby reflux for 3.5 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationSubsequently, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-735b1e9d3daa46ca9a9131f41cfffbec
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

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