Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | HCID 89648955 | HCID 89648955 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 89662101 | HCID 89662101 | — |
Reaction Steps
2.57 g of methyl 1-benzyl-5-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrazole-3-carboxylate (7.06 mmol, 1.0 eq.) were dissolved in 51 mL of dry 1,2-dimethoxyethane under nitrogen atmosphere. 1.52 g of cyclopropylboronic acid (17.6 mmol, 2.5 eq.), 2.62 g of sodium carbonate (24.7 mmol, 3.5 eq.) and 408 mg of tetrakis(triphenylphosphin)palladium(0) (0.353 mmol, 0.05 eq.) were added and the mixture was stirred for 24 hours at 75° C. bath temperature. Then the mixture was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue purified by flash chromatography to give 1.61 g (5.39 mmol, 76%) of analytically pure target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09422268B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-b2beece17af74ae2826439d210120b51 |
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| Source note | uspto-grants-2016_08 |
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