Potassium Iodide → HCID 16063478, compound

HRID 1993919Notes

Reaction equation

HRID 1993919 reaction equation
Br[CH2:2][C:3]1[N:7]([CH3:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[C:4]=1[CH:16]1[CH2:18][CH2:17]1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O.CCOC(C)=O>[CH:16]1([C:4]2[C:5](=[O:15])[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:7]([CH3:8])[C:3]=2[CH2:2][O:26][C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)[CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 68677142HCID 68677142, compound

Product 1

HCID 16063478HCID 16063478, compoundYield 22.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromomethyl-4-cyclopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.094 g) in acetonitrile (5 mL), was added 4-fluorophenol (0.034 g), caesium carbonate (0.1 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 afforded the desired 4-cyclopropyl-5-(4-fluoro-phenoxymethyl)-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.023 g) as a light beige solid. MS (ESI+): 339.1 ([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 in vacuo

Sources & evidence

ORD record
ord-d90d389c689941e287a7b8f4d08ef4e1
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

Loading…