Potassium Carbonate → ethyl 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxylate

HRID 639974Notes

Reaction equation

HRID 639974 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl[CH2:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:25][C:21]1[CH:20]=[C:19]([NH:18][C:16](=[O:17])[CH2:15][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6]2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23889312-chloro-N-(3-fluorophenyl)acetamideHCID 178470496HCID 178470496, compound

Product 1

HCID 68638240ethyl 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 4-nitro-1H-pyrazole-3-carboxylate (0.685 g, 3.7 mmol) and 2-chloro-N-(3-fluorophenyl) acetamide (0.694 g, 3.7 mmol) and potassium carbonate (0.613 g, 4.44 mmol) in dimethyl formamide (10 ml) was stirred at room temperature for 20 hours. The mixture was evaporated and the residue was purified by silica gel chromatography eluting with a 8 to 10% mixture of ethyl acetate in dichloromethane to give ethyl 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxylate (0.920 g, 74% yield):

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a 8 to 10% mixture of ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-0c7ce77ca11f4c6f82d9997a73c036cd
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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