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

HRID 1631922Notes

Reaction equation

HRID 1631922 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].Br[CH2:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[C:9]([CH3:10])=[N:8][N:7]([CH2:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[C:6]=1[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7131483methyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetateHCID 112064214-(Bromomethyl)benzaldehyde

Product 1

HCID 86661579[1-(4-Formyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3,5-Dimethyl-1H-pyrazol-4-yl)-acetic acid methyl ester (1 g, 6.0 mmol), 4-(bromomethyl)-benzaldehyde (1.18 g, 6.0 mmol) and K2CO3 (1.73 g, 12.5 mmol) were refluxed in 5 ml acetonitrile for 12 h. After cooling, the mixture was filtered, and the solvent was removed under reduced pressure. The residue was purified by MPLC (silica gel, CH2Cl2/methanol 99:1).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by MPLC (silica gel, CH2Cl2/methanol 99:1)

Sources & evidence

ORD record
ord-49a64262cafc40d4adafe6e518fb7707
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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