Cesium carbonate → methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate

HRID 547509Notes

Reaction equation

HRID 547509 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][NH:7][N:6]=1)=[O:4].[C:13](=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.IC>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:13])[N:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])=[O:4]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 178499180HCID 178499180, compound

Product 1

HCID 1255549methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylateYield 30%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolvent

Procedure

340 mg (1.99 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 110 mg (30%) of the title compound and 195 mg (53%) of the compound of Preparative Example 7.

Workup

  1. additionwere added dropwise
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionthe resultant was extracted with ethyl acetate and brine
  4. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure
  7. customThe resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0415d0bd123e498ca60109542f16b5d5
Source dataset
uspto-grants-2011_05
Patent number
US07939550B2

Reaction notes

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