Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Furan-3-boronic acid | HCID 2734358 | — |
| Reactant | HCID 60141907 | HCID 60141907 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 86668515 | HCID 86668515 | 17% |
Reaction Steps
The tube was charged with 4-bromo-3-(2-chloro-6-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole (30 mg, 0.06 mmol), tetrakis(triphenylphosphine)palladium(0) (0.010 g), 1.5 mL 1,2-Dimethoxyethane and was purged with argon. Then furan-3-ylboronic acid (0.012 g, 0.1 mmol) and an aqueous solution of cesium carbonate (0.05 g in 0.2 mL) were added. The reaction mixture was heated under microwave irradiation to 100° C. for 2 h. The solvent was evaporated and the product was isolated by column chromatography (hexane:ethyl acetate 25: I) to obtain 5 mg (17%) of a yellowish solid of example I-13. As a major side reaction, hydrodebromination was observed.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08592456B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-505f2f505f64492c9a5345d86828e4e9 |
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| Source note | uspto-grants-2013_11 |
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