Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 2-Aminooxazole | HCID 558521 | — |
| Edukt | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Edukt | N-(2-Bromopyridin-4-yl)-2,6-dichlorobenzamide | HCID 75464886 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | HCID 49839566 | HCID 49839566 | 9% |
Reaktionsschritte
To a microwave tube was added N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.30 g, 0.87 mmol), 2-aminooxazole (0.11 g, 1.0 mmol), Pd2(dba)3 (0.078 g, 0.087 mmol), XantPhos (0.096 g, 0.17 mmol), Cs2CO3 (0.57 g, 1.7 mmol) and dioxane (5 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 140° C. for 3 hours and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was dissolved in DMF and purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product as a yellow solid (26 mg, yield: 9%). 1H NMR (500 MHz, DMSO-d6): δ 11.2 (s, 1H), 8.28 (s, 1H), 8.17 (d, J=5.5 Hz, 1H), 7.71 (s, 1H), 7.59 (d, J=7.5 Hz, 2H), 7.52 (t, J=3.5 Hz, 1H), 7.41 (m, 1H), 7.03 (s, 1H). LC-MS (ESI) m/z: 349.0 [M+H+].
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08486950B2 |
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| Quelldatensatz | uspto-grants-2013_07 |
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| ORD ID | ord-4deb55779a0a435eab3663dfe7a419cd |
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| Quellennotiz | uspto-grants-2013_07 |
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