Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | 3,5-Dimethylisoxazole-4-boronic acid pinacol ester | HCID 2758656 | — |
| Reactant | HCID 83382776 | HCID 83382776 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 123172170 | HCID 123172170 | 134.1% |
Reaction Steps
5-bromo-1-methyl-4-phenyl-1H-pyrazole (87 mg, 0.37 mmol) and 3,5-Dimethylisoxazole-4-boronic acid pinacol ester (373 mg, 1.47 mmol) was added to a 1,4-dioxane (2 ml). To the above mixture were added Pd(dppf)Cl2 (27 mg, 0.037 mmol) and potassium acetate (181 mg, 1.85 mmol). The reaction mixture was heated at 100° C. for 2 h. The reaction mixture was then diluted with EtOAc (100 ml), washed with bring (50 ml×2). The organic solvent was evaporated and the residue was dissolved in DCM and purified with combi-flash column chromatography (product came out at 45% EtOAc/Hexane) to afford 141 mg product 1-methyl-4-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09255089B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-77d7905b1d1346968e2765f21546c72a |
|---|
| Source note | uspto-grants-2016_02 |
|---|
