Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | 4-Fluorophenol | HCID 9732 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 68677647 | HCID 68677647 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 16063479 | HCID 16063479 | 16.1% |
Reaction Steps
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]+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07652057B2 |
|---|
| Source dataset | uspto-grants-2010_01 |
|---|
| ORD ID | ord-ca191a327ce54eaba3be33c5c2bcf102 |
|---|
| Source note | uspto-grants-2010_01 |
|---|