Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-(Trifluoromethyl)phenylboronic acid | HCID 2734388 | — |
| Reactant | HCID 86711541 | HCID 86711541 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86711540 | HCID 86711540 | — |
Reaction Steps
A mixture of 5-bromo-1-(4-cyano-benzyl)-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 12b, 0.56 g, 1.68 mmol), 3-(trifluoromethyl)phenylboronic acid (0.39 g, 2.05 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (75 mg, 0.10 mmol) and Cs2CO3 (0.82 g, 2.51 mmol) in dioxane (4 mL) is heated for 24 h at 60° C. The reaction mixture is acidified with acetic acid and purified by preparative reversed-phase HPLC (Sunfire, gradient of methanol in water, 0.1% TFA, 60° C.). Yield: 186 mg (28% of theory); ESI mass spectrum: [M+H]+=399; Retention time HPLC: 1.22 min (Z002—002).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09102624B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-da478e273eb14b268a5e802733d93de4 |
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| Source note | uspto-grants-2015_08 |
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