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 58503716 | HCID 58503716 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90390339 | HCID 90390339 | 36% |
Reaction Steps
The nitrile 25H (1.25 g, 6.4 mmol), 4-trifluoromethylphenylboronic acid (1.34 g, 1 mol eq), palladium acetate (29 mg, 0.02 mol eq), cesium carbonate (4.16 g, 2 mol eq), and XPhos (137 mg, 0.04 mol eq) were mixed, placed under a nitrogen atmosphere and dioxane (8 mL) was added. The mixture was heated at 100° C. for 4 h. After cooling, the mixture was filtered through a celite pad, washed with dioxane (2×30 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (9.5/0.5 Petroleum ether/EtOAc) to afford 26M as yellow solid (0.65 g, 36% Yield). 1HNMR (DMSO, 200 MHz) δ 1.37 (d, 6H, J=3.9), 5.15 (m, 1H), 6.7 (s, 1H), 7.32 (s, 1H), 7.87 (d, 2H, J=7.8), 8.33 (d, 2H, J=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-523592b1585645c1b3b6cdce957fee6b |
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| Source note | uspto-grants-2016_08 |
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