Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Potassium benzyltrifluoroboranuide | HCID 23692459 | — |
| Reactant | HCID 86648127 | HCID 86648127 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | HCID 86648128 | HCID 86648128 | 59% |
Reaction Steps
A flask was charged with ethyl 7-(anthracen-9-ylmethoxy)-4-iodo-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (200 mg, 0.33 mmol), potassium benzyltrifluoroborate (80 mg, 0.4 mmol), PdCl2(dppf) (27 mg, 0.033 mmol) and cesium carbonate (326 mg, 1.0 mmol). The flask was evacuated and refilled with nitrogen. THF (4 mL) and water (0.4 mL) were added and the mixture was refluxed for 16 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 0.5M hydrochloric acid. The aqueous layer was extracted with additional EtOAc and the organic layer was dried over MgSO4. After evaporation of solvent, the crude residue was purified by flash chromatography (0-30% EtOAc/hexanes) to give 110 mg of the title compound. MS: (+) m/z 565.38 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08269008B2 |
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| Source dataset | uspto-grants-2012_09 |
|---|
| ORD ID | ord-842fa25d33484983a4f783bb86de8136 |
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| Source note | uspto-grants-2012_09 |
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