Potassium Iodide → HCID 16063479, compound

HRID 1993923Notes

Reaction equation

HRID 1993923 reaction equation
Br[CH2:2][C:3]1[N:7]([CH3:8])[N:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:5](=[O:16])[C:4]=1[CH:17]1[CH2:19][CH2:18]1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O.CCOC(C)=O>[CH:17]1([C:4]2[C:5](=[O:16])[N:6]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[N:7]([CH3:8])[C:3]=2[CH2:2][O:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[CH2:19][CH2:18]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 68677647HCID 68677647, compound

Product 1

HCID 16063479HCID 16063479, compoundYield 16.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromomethyl-4-cyclopropyl-2-(4-fluoro-phenyl)-1-methyl-1,2-dihydro-pyrazol-3-one (0.130 g) in acetonitrile (5 mL), was added 4-fluorophenol (0.045 g), caesium carbonate (0.13 g) and potassium iodide (3 crystals). The reaction was stirred overnight at ambient temperature and was then diluted with water and EtOAc. The phases were separated and the aqueous was extracted with further EtOAc. The combined organic phases were washed with further HCl solution, brine and dried with sodium sulfate. Filtration and evaporation of the volatiles in vacuo and purification of the residue via ISCO Combiflash chromatography (using EtOAc/heptane) afforded the desired 4-cyclopropyl-5-(4-fluoro-phenoxymethyl)-2-(4-fluoro-phenyl)-1-methyl-1,2-dihydro-pyrazol-3-one (0.023 g) as a light beige solid. MS (ESI+): 357.0 ([M+H]+).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous was extracted with further EtOAc
  3. washThe combined organic phases were washed with further HCl solution, brine
  4. dry with materialdried with sodium sulfate
  5. filtrationFiltration and evaporation of the volatiles
  6. customin vacuo and purification of the residue via ISCO Combiflash chromatography (using EtOAc/heptane)

Sources & evidence

ORD record
ord-ca191a327ce54eaba3be33c5c2bcf102
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

Loading…