Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetramethyltin | HCID 11661 | — |
| Reactant | HCID 136399879 | HCID 136399879 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 136399880 | HCID 136399880 | 49.8% |
Reaction Steps
A mixture of 7-bromo-4-hydroxy-3-phenyl-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (231 mg, 0.64 mmol), tetramethyltin (177 μl, 1.28 mmol), bis(triphenylphosphine)palladium(II) dichloride (45 mg, 0.06 mmol), and dimethylformamide (2.5 ml) was stirred at 130° C. for 1 h before it was cooled to room temperature, quenched with water, and filtered. The filtrate was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (95 mg): MS: (+) m/z 299.49 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08269008B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-e6d50c8e577b498e8c69c0f23398bbe5 |
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| Source note | uspto-grants-2012_09 |
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