Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-(difluoroMethoxy)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-aMine | HCID 49853531 | — |
| Reactant | HCID 118161758 | HCID 118161758 | — |
| Catalyst | Cuprous 2-thiophenecarboxylate | HCID 11194830 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | HCID 118161578 | HCID 118161578 | 23% |
Reaction Steps
To a solution of 3,3-bis(methylthio)-1-(spiro[bicyclo[3.1.0]hexane-3,3′-oxetan]-6-yl)prop-2-en-1-one (250 mg, 924 mmol) in 6:1 tetrahydrofuran/water (3.5 mL) was added 3-(difluoromethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (317 mg, 1.11 mmol), copper(I) thiophene-2-carboxylate (353 mg, 1.85 mmol), cesium carbonate (602 mg, 1.85 mmol), and bis(triphenylphosphine)palladium(II) dichloride (65 mg, 92 mmol). The reaction mixture was heated at 110° C. with microwave irradiation for 1.5 h. The reaction mixture was concentrated, and the resulting residue was purified by flash column chromatography (ethyl acetate) to afford product as a white solid (0.080 g, 23%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365583B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-8705a0e5109040819c943f678c03e431 |
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| Source note | uspto-grants-2016_06 |
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