Potassium Carbonate → HCID 86723024, compound

HRID 522311Notes

Reaction equation

HRID 522311 reaction equation
Br[CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]1=[O:9].[Cl:10][C:11]1[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][NH:14][C:15]=1[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:10][C:11]1[C:12]([C:17]([F:19])([F:18])[F:20])=[N:13][N:14]([CH:2]2[CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]2=[O:9])[C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12069654-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazoleHCID 10954409HCID 10954409, compound

Product 1

HCID 86723024HCID 86723024, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-bromooxepan-2-one (1 g, 5.18 mmol) in DMF (10 mL) was added 4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazole (0.956 g, 5.18 mmol), followed by potassium carbonate (1.07 g, 7.74 mmol). The reaction mixture was then heated at 65° C. for 8 h. After cooling to room temperature, the reaction mixture was partitioned between water (20 mL) and ethyl acetate (30 mL). The organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography (SiO2, 25% EtOAc/hexanes) gave the title product as a white solid (0.3 g, 1.01 mmol, 20%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between water (20 mL) and ethyl acetate (30 mL)
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (SiO2, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-97e28a6608b441cca0be87cef814a802
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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