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

HRID 340487

Reaction equation

HRID 340487 reaction equation
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

Participants

6

Reactant 5

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-735b1e9d3daa46ca9a9131f41cfffbec
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Linked notes

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