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 | 2-Chloro-6-morpholin-4-yl-isonicotinonitrile | HCID 83074581 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90390501 | HCID 90390501 | 40% |
Reaction Steps
The nitrile 25B (3.2 g, 14.4 mmol), 4-trifluoromethylphenylboronic acid (3.01 g, 1 mol eq), palladium acetate (65 mg, 0.02 mol eq), cesium carbonate (9.38 g, 2 mol eq), and XPhos (265 mg, 0.04 mol eq) were mixed, placed under a nitrogen atmosphere and dioxane (12 mL) was added. The mixture was heated at 100° C. overnight. 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 (7/3 Petroleum ether/EtOAc) to afford 26B as yellow solid (1.33 g, 40% Yield). 1HNMR (DMSO, 400 MHz) δ 3.63 (m, 4H, J=1.9), 3.74 (m, 4H, J=2), 7.38 (s, 1H), 7.74 (s, 1H), 7.84 (d, 2H, J=8.1), 8.32 (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-c0695b072a034e42b471519c8320ef1a |
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| Source note | uspto-grants-2016_08 |
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