Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Ethyl 2-aminobenzoate | HCID 6877 | — |
| Edukt | Binap, (A+-)- | HCID 634876 | — |
| Edukt | Sodium t-butoxide | HCID 23676156 | — |
| Edukt | 5-Bromo-2-(3-methoxyphenyl)pyridine | HCID 49758519 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Produkt | Ethyl acetate hexane | HCID 21226206 | 98,4% |
| Produkt | 2-(6-(3-Methoxyphenyl)pyridin-3-ylamino)benzoic acid | HCID 25186999 | — |
Reaktionsschritte
In a schlenck tube, a mixture of 5-bromo-2-(3-methoxyphenyl)pyridine (Intermediate 27, 0.91 mmol, 0.23 g), ethyl 2-aminobenzoate (Intermediate 33, 0.91 mmol, 0.15 g), BINAP (0.05 mmol, 0.028 g), Pd2(dba)3 (0.05 mmol, 0.042 g) and NaOtBu (1.82 mmol, 0.175 g) in toluene (4 ml) was heated at 110° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the solid residue was triturated with aqueous solution of 2N HCl and extracted with CHCl3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.078 g (yield 26%) of the expected compound.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08536165B2 |
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| Quelldatensatz | uspto-grants-2013_09 |
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| ORD ID | ord-0c6010783c884be28f919b4217d37301 |
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| Quellennotiz | uspto-grants-2013_09 |
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