Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetramethyltin | HCID 11661 | — |
| Reactant | HCID 86617356 | HCID 86617356 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68427942 | HCID 68427942 | 56.7% |
Reaction Steps
A mixture of 4-bromo-2-(4-fluoro-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (140 mg, 0.35 mmol), tetramethyltin (98 μL, 0.70 mmol) and bis(triphenylphosphine)palladium(II) dichloride (25 mg, 0.03 mmol) in dimethylformamide (2.5 mL) was stirred at 130° C. for 45 min before it was cooled to room temperature, quenched with water, 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 hexanes to give the title compound as a white solid (66 mg): MS: (+) m/z 333.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07696223B2 |
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| Source dataset | uspto-grants-2010_04 |
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| ORD ID | ord-d800d205ce70494393be7f3594e82066 |
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| Source note | uspto-grants-2010_04 |
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