Potassium Carbonate → HCID 67111083, compound

HRID 540751Notes

Reaction equation

HRID 540751 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH2:12]([N:14]1[C:18]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])=[CH:17][C:16](=[O:27])[NH:15]1)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:12]([N:14]1[C:18]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])=[CH:17][C:16]([O:27][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)=[N:15]1)[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 67111066HCID 67111066, compound

Product 1

HCID 67111083HCID 67111083, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

1-fluoro-4-(trifluoromethyl)benzene (2.5 mL, 20 mmol, 6.0 equiv) was added to a mixture of 3-(2-ethyl-5-oxo-2,5-dihydro-1H-pyrazol-3-yl)benzonitrile (688 mg, 3.23 mmol, 1 equiv) and potassium carbonate (1.11 g, 8.07 mmol, 2.50 equiv) in dimethyl sulfoxide (8 mL) in a high pressure reaction vessel. The vessel was sealed, and the reaction mixture was heated to 160° C. After stirring for 4 hours, the high pressure vessel was cooled to 22° C. and the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography (hexanes, grading to 40% ethyl acetate-hexanes) to afford 3-{1-ethyl-3-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-5-yl}benzonitrile (700 mg, 61%) as a white solid. Calcd (M+1)+: 358.1. Found: 358.0.

Workup

  1. customThe vessel was sealed
  2. temperaturethe high pressure vessel was cooled to 22° C.
  3. customthe reaction mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialthe washed solution was dried over sodium sulfate
  6. filtrationThe dried solution was filtered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by flash-column chromatography (hexanes, grading to 40% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-088c2cb33e674c52b2ff384a779be932
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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