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Use of a catalytic co-solvent, N,N-dimethyl octanamide, allows the flow synthesis of Gleevec with no solvent switch

Accepted version
Peer-reviewed

Type

Article

Change log

Authors

Yang, Jeffrey 
Niu, Dawen 
Buchwald, Stephen 

Abstract

A general, efficient method for C−N cross‐coupling has been developed using N,N‐dimethyloctanamide as a catalytic cosolvent for biphasic continuous‐flow applications. The described method was used to generate a variety of biarylamines and was integrated into a two‐step sequence which converted phenols into biarylamines via either triflates or tosylates. Additionally, the method was applied to a three‐step synthesis of imatinib, the API of Gleevec, in good yield without the need of solvent switches.

Description

Keywords

biaryls, cross-coupling, flow chemistry, palladium, synthetic methods, Amides, Catalysis, Imatinib Mesylate, Solvents

Journal Title

Angewandte Chemie - International Edition

Conference Name

Journal ISSN

1521-3773
1521-3773

Volume Title

55

Publisher

John Wiley & Sons Ltd.