Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | HCID 83074072 | HCID 83074072 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 125505052 | HCID 125505052 | 68% |
Reaction Steps
The nitrile 25C (2.0 g, 11.1 mmol), 4-trifluoromethylphenylboronic acid (2.32 g, 1.1 mol eq), palladium acetate (50 mg, 0.02 mol eq), cesium carbonate (7.23 g, 2 mol eq), and XPhos (210 mg, 0.04 mol eq) were mixed, placed under a nitrogen atmosphere and dioxane (10 mL) was added. The mixture was heated at 100° C. for 3 h. After cooling, the mixture was filtered through a celite pad, washed with dioxane (2×20 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (9.5/0.5 petroleum ether/EtOAc) to afford 26E as a pale yellow solid (2.2 g, 68% Yield). 1HNMR (DMSO, 200 MHz) δ 3.13 (s, 6H), 7.12 (s, 1H), 7.58 (s, 1H), 7.82 (d, 2H, J=7.7), 8.30 (d, 2H, J=7.8).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409864B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-ac569078074d4dd8b199d534dd26fe36 |
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| Source note | uspto-grants-2016_08 |
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