Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(Bromomethyl)benzonitrile | HCID 89599 | — |
| Reactant | HCID 71257690 | HCID 71257690 | — |
| Reactant | HCID 178498589 | HCID 178498589 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67361802 | HCID 67361802 | 86.4% |
Reaction Steps
1-(2-Fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid methyl ester (200 mg, 0.847 mmol) were dissolved in 5 ml of DMF and cesium carbonate (552 mg, 1.7 mmol) and 2-bromomethyl-benzonitrile (166 mg, 0.85 mmol) were added. The mixture was stirred for 5 h at 60° C., filtrated and the solvent was removed in vacuo. The obtained residue of crude 5-(2-cyano-benzyloxy)-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid methyl ester (235 mg, 79%) was dissolved in a mixture of THF, MOH and water (3 ml each), lithium hydroxide (64.1 mg, 2.7 mmol) was added, and the mixture was stirred overnight at room temperature. After evaporation of the solvent the residue was subjected to column chromatography (silica gel, DCM/MOH 9:1) to give 195 mg (86%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08664257B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-0cd5b384b5864f668dd840a368fa0883 |
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| Source note | uspto-grants-2014_03 |
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