Potassium Carbonate → 2-(1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 1946330Notes

Reaction equation

HRID 1946330 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[C:32]([F:35])([F:34])[F:33]>CN(C=O)C.C(Cl)Cl.O.[Cl-].[Na+].O>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:1]2[CH:5]=[CH:4][C:3]([N:6]3[C:14](=[O:15])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7]3=[O:16])=[N:2]2)=[C:26]([C:32]([F:33])([F:34])[F:35])[CH:27]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 34925974-Chloro-2-(trifluoromethyl)benzyl bromideHCID 178514958HCID 178514958, compound

Product 1

HCID 667707212-(1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-(1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione (for a preparation see Intermediate 28)(3 g, 14.1 mmol) and potassium carbonate (2.92 g, 21.1 mmol) in DMF (30 ml) was stirred under nitrogen at ambient temperature for 5 min. To the pale yellow suspension was added 1-(bromomethyl)-4-chloro-2-(trifluoromethyl)benzene (3.85 g, 14.07 mmol, Alfa Aesar). The mixture turned to a colourless suspension. The reaction mixture was stirred at ambient temperature under nitrogen overnight. The reaction mixture was diluted with DCM (50 ml) and water (50 ml). To the emulsion was added brine (30 ml). The resulting phases were separated and the aqueous layer further extracted with DCM (50 ml). The combined organic extracts were filtered through a hydrophobic frit and the solvent removed in vacuo to give 2-(1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione (6.14 g) as an off-white gum.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature under nitrogen overnight
  2. customThe resulting phases were separated
  3. extractionthe aqueous layer further extracted with DCM (50 ml)
  4. filtrationThe combined organic extracts were filtered through a hydrophobic frit
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2aa50f8131144cafb6420e1f8910a2a3
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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