Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Tricyclohexylphosphine | HCID 75806 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | 1-(6-Bromopyridin-3-yl)-2,2,2-trifluoroethan-1-ol | HCID 71301986 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68210800 | HCID 68210800 | — |
Reaction Steps
In 1,4-dioxane (2.0 mL) was dissolved 1-(6-bromopyridin-3-yl)-2,2,2-trifluoroethanol (98.6 mg, 0.385 mmol). To the solution were added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (120 mg, 0.578 mmol), cesium carbonate (188 mg, 0.578 mmol), tris(dibenzylideneacetone)dipalladium (5.3 mg, 0.0058 mmol), tricyclohexylphosphine (3.9 mg, 0.0139 mmol) and water (0.2 mL), and the mixture was stirred at 80° C. for 2 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=19/1) to give Compound A26 (94.5 mg, 950 yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150569B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-2b66feef6cbe49fda5abb810dbcb5409 |
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| Source note | uspto-grants-2015_10 |
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