Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tributylvinyltin | HCID 81998 | — |
| Reactant | N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide | HCID 86012996 | — |
| Catalyst | 2,6-Di-tert-butyl-4-methylphenol | HCID 31404 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68808761 | HCID 68808761 | 61.5% |
Reaction Steps
To a solution of N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (2 g) in dimethylformamide (6 mL) was added tributyl(vinyl)tin (3.63 g), 2,6-di-tert-butyl-4-methylphenol (50 mg) and dichlorobis(triphenylphosphine)palladium (0.25 g). The reaction was heated at 80° C. under nitrogen for 6 hours and then cooled to room temperature. The mixture was filtered through diatomaceous earth and poured into water and dichloromethane. The organic layer was separated and the aqueous was further extracted with dichloromethane. The combined organic layers were dried, filtered and evaporated. Purification (SiO2, methanol:dichloromethane 5:95 as eluant) gave the sub-titled compound (1.2 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07408065B2 |
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| Source dataset | uspto-grants-2008_08 |
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| ORD ID | ord-4b11e245835b411d84a506285fe1d482 |
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| Source note | uspto-grants-2008_08 |
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