Water → [3,5-Dimethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid methyl ester

HRID 1631901Notes

Reaction equation

HRID 1631901 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[C:6]([CH3:11])=[N:7][NH:8][C:9]=1[CH3:10].[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14].C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[C:9]([CH3:10])=[N:8][N:7]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)[C:6]=1[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 7131483methyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetate

Product 1

HCID 66707610[3,5-Dimethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3,5-dimethyl-1H-pyrazol-4-yl)-acetic acid methyl ester (3.90 g, 23 mmol, Enamine EN300-15247) and 4-nitrobenzyl bromide (4.60 g, 20.7 mmol) in acetonitrile was added K2CO3 (2.76 g, 19.9 mmol) and the mixture was stirred for one hour at room temperature. The reaction mixture was poured into water and extracted twice with ethyl acetate. The organic phase was dried over MgSO4 and evaporated under reduced pressure.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-78d2e69778c04553ac302ccd7c0c6084
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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