Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | N-(4-Iodophenyl)acetamide | HCID 12147 | — |
| Reactant | Bis(cyclohexylmethyl)amine | HCID 4594378 | — |
| Reactant | Tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate | HCID 68959213 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 68957316 | HCID 68957316 | — |
Reaction Steps
To N,N-dimethylacetamide 3.0 mL solution of tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate 0.15 g were added N-(4-iodophenyl)acetamide 0.37 g, N,N-dicyclohexylmethylamine 0.41 mL and palladium acetate 5.4 mg at room temperature, and it was stirred at 130° C. for 4 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, and the solvent was removed under reduced pressure after sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=1:1] to give tert-butyl 4-((E)-2-(4-(acetamido)phenyl)vinyl)-2-(4-fluoroanilino)benzoate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08327467B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-b3b6b3cc45094ee89fe99c254ac17a09 |
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| Source note | uspto-grants-2012_12 |
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