Potassium Carbonate → [1-(4-Bromobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester

HRID 1631935Notes

Reaction equation

HRID 1631935 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].C([O-])([O-])=O.[K+].[K+].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>CC#N>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[C:9]([CH3:10])=[N:8][N:7]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([Br:19])=[CH:21][CH:22]=2)[C:6]=1[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 7131483methyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetate

Product 1

HCID 63276242[1-(4-Bromobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl esterYield 71.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3,5-dimethyl-1H-pyrazol-4-yl)-acetic acid methyl ester (30.7 g) (preparation according to WO2007/141267) in CH3CN (500 ml) was added K2CO3 (43.5 g) and 4-bromobenzylbromide (38.6 g) and the reaction heated to reflux. After 15 h, the reaction was cooled and filtered, the filtrate was then concentrated. The residue was recrystallized from cyclohexane to afford 37.3 g of the title compound.

Workup

  1. temperaturethe reaction heated to reflux
  2. temperaturethe reaction was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was then concentrated
  5. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-055f0592250c4754ab9e829285dd72b4
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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