An Advantageous Route to Oxcarbazepine (Trileptal) Based on Palladium-Catalyzed Arylations Free of Transmetallating Agents
2005; American Chemical Society; Volume: 7; Issue: 22 Linguagem: Inglês
10.1021/ol051291p
ISSN1523-7060
AutoresMónica Carril, Raúl SanMartı́n, Fátima Churruca, Imanol Tellitu, Esther Domı́nguez,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoA 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.
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