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An Advantageous Route to Oxcarbazepine (Trileptal) Based on Palladium-Catalyzed Arylations Free of Transmetallating Agents

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journal contribution
posted on 27.10.2005, 00:00 by Mónica Carril, Raul SanMartin, Fátima Churruca, Imanol Tellitu, Esther Domínguez
A new route to oxcarbazepine (Trileptal), the most widely prescribed antiepileptic drug, starting from commercially available 2‘-aminoacetophenone and 1,2-dibromobenzene, is reported. The sequentially accomplished key steps are palladium-catalyzed intermolecular α-arylation of ketone enolates and intramolecular N-arylation reactions. After several experiments to establish the best conditions for both arylation processes, the target oxcarbazepine is obtained in a satisfactory overall yield, minimizing the number of steps and employing scalable catalytic procedures developed in partially aqueous media.