Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Edukt | 2-Chloro-6-(pyrrolidin-1-yl)pyridine-4-carbonitrile | HCID 83074580 | — |
| Katalysator | palladium(II) acetate | HCID 167845 | — |
| Katalysator | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | HCID 66832355 | HCID 66832355 | 92% |
Reaktionsschritte
2-Chloro-6-pyrrolidin-1-yl-isonicotinonitrile (0.18 g, 0.87 mmol), 4-trifluoromethylphenylboronic acid (0.18 g, 0.95 mmol), palladium acetate (3.9 mg, 0.02 mmol), cesium carbonate (0.56 g, 1.73 mmol), and XPhos (17 mg, 0.04 mmol) were combined, placed under a nitrogen atmosphere and dioxane (1.0 mL) was added. The reaction vessel was sealed and heated to 100° C. for 2 hours. The reaction mixture was cooled to rt, filtered through celite, concentrated under reduced pressure and purified by flash column chromatography (0%-80% EtOAc in hexane) to provide the desired product (253 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 8.11 (d, J=8.1 Hz, 2H), 7.70 (d, J=8.2 Hz, 2H), 7.15 (d, J=0.8 Hz, 1H), 6.54 (d, J=0.9 Hz, 1H), 3.55 (bs, 4H), 2.13-1.99 (m, 4H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08614201B2 |
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| Quelldatensatz | uspto-grants-2013_12 |
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| ORD ID | ord-6a7a22c1c5774919996decbdd2dafcfb |
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| Quellennotiz | uspto-grants-2013_12 |
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