Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 58072367 | — |
| Reactant | HCID 89586574 | HCID 89586574 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 68014904 | HCID 68014904 | 8.8% |
Reaction Steps
5-oxo-2-[3-(trifluoromethyl)phenyl]-2,5-dihydropyridazin-4-yl trifluoromethanesulfonate (0.100 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.139 g), sodium carbonate (0.109 g) and tetrakis(triphenylphosphine)palladium(0) (0.0298 g) were suspended in a mixed solvent of toluene (2.06 mL), ethanol (0.52 mL) and water (0.52 mL), and the suspension was stirred at 100° C. for 6 hr under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated, purified by NH silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (0.0087 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150588B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-f5599760591c47e498135494c97a990e |
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| Source note | uspto-grants-2015_10 |
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