Potassium Carbonate → 5-chloro-1-phenyl-3-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carbaldehyde

HRID 402757Notes

Reaction equation

HRID 402757 reaction equation
O=P(Cl)(Cl)[Cl:3].[C:6]1([N:12]2[C:16](=O)[CH2:15][C:14]([C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=3[F:26])=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:27](=[O:30])([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:3][C:16]1[N:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:13]=[C:14]([C:18]2[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=2[F:26])[C:15]=1[CH:27]=[O:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 667650912-phenyl-5-(2,4,5-trifluorophenyl)-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 866852625-chloro-1-phenyl-3-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

DMF (0.257 mL, 3.32 mmol) was added to a stirred mixture of POCl3 (0.722 mL, 7.74 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 5 minutes. Then 2-phenyl-5-(2,4,5-trifluorophenyl)-2,4-dihydro-3H-pyrazol-3-one (321 mg, 1.106 mmol) in DMF (1 mL) was added slowly to the reaction mixture at 0° C. and the reaction mixture was heated at 70° C. for 16 hours. It was then poured into a cooled saturated solution of potassium carbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (Biotage 12M) eluting with EtOAc/hexanes to give the product as a colorless solid.

Workup

  1. temperaturethe reaction mixture was heated at 70° C. for 16 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (Biotage 12M)
  8. washeluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-7334d026204549098c632de7f9812c5d
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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