Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3,5-Dimethylisoxazole-4-boronic acid | HCID 2734346 | — |
| Reactant | HCID 67120035 | HCID 67120035 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67120034 | HCID 67120034 | 59% |
Reaction Steps
5-Bromo-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole (287 mg, 0.97 mmol), 3,5-dimethylisoxazol-4-ylboronic acid (274 mg, 1.94 mmol), K2CO3 (806 mg, 5.83 mmol), sodium iodide (291 mg, 1.94 mmol) and Pd(PPh3)4 (90 mg, 0.08 mmol) were mixed with degassed dioxane (1 mL) and degassed H2O (1 mL) under nitrogen in a microwave vial. The reaction was heated at 150° C. for 20 min. The crude mixture was diluted with CH2Cl2 and washed with water. The organic phase was separated from the water phase, dried using a phase separator and evaporated. The crude product was purified on silica column (CH2Cl2:Et2O, 90:10) to give 4-(1-(4-methoxyphenyl)-3-propyl-1H-pyrazol-5-yl)-3,5-dimethylisoxazole (178 mg, 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921402B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-e65705603d98428e88690645ef86f340 |
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| Source note | uspto-grants-2014_12 |
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