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

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 in...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2005-10, Vol.7 (22), p.4787-4789
Main Authors: Carril, Mónica, SanMartin, Raul, Churruca, Fátima, Tellitu, Imanol, Domínguez, Esther
Format: Article
Language:English
Subjects:
Acetophenones - chemistry
Anticonvulsants - chemical synthesis
Anticonvulsants - chemistry
Bromobenzenes - chemistry
Carbamazepine - analogs & derivatives
Carbamazepine - chemical synthesis
Carbamazepine - chemistry
Catalysis
Ketones - chemistry
Molecular Structure
Palladium - chemistry
Time Factors
Water - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051291p