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

HRID 1620094Notes

Reaction equation

HRID 1620094 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-4dc39f3a01484349b102410e852a7f98
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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