Potassium Carbonate → (4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-(3-methoxy-phenyl)-acetic acid ethyl ester

HRID 1372136Notes

Reaction equation

HRID 1372136 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[N:4][NH:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[C:12](=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20](=[O:31])[CH:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1>CC#N>[CH2:18]([O:19][C:20](=[O:31])[CH:21]([N:4]1[C:3]([CH3:11])=[C:2]([Cl:1])[C:6]([C:7]([F:9])([F:10])[F:8])=[N:5]1)[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 289522Methyl 2-bromo-2-(3-methoxyphenyl)acetateHCID 178434610HCID 178434610, compound

Product 1

HCID 68423509(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-(3-methoxy-phenyl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Chloro-3-methyl-5-trifluoromethyl-1H-pyrazole (610 mg, 3.3 mmol) was taken into dry CH3CN (15 ml), dry potassium carbonate (1.15 g) was added to this and the resulting mixture stirred at room temperature for 1 h under nitrogen. Bromo-(3-methoxy-phenyl)-acetic acid methyl ester (900 mg, 2.8 mmol) in CH3CN (5 ml) was then added to the mixture through a syringe. The reaction was then heated at reflux for 10 h, cooled and then filtered through a celite filter bed. The filtrate was concentrated to obtain (4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-(3-methoxy-phenyl)-acetic acid ethyl ester that was purified by column chromatography on silica (pet ether/ethyl acetate)

Workup

  1. additionwas added to this and the resulting mixture
  2. temperatureThe reaction was then heated
  3. temperatureat reflux for 10 h
  4. temperaturecooled
  5. filtrationfiltered through a celite filter bed
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-53424b5217254a8bb6248c4df421d532
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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