Use of a “Catalytic” Cosolvent, N,N-Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch

Yang, Jeffrey C.; Niu, Dawen; Karsten, Bram P.; Lima, Fabio; Buchwald, Stephen L.

Use of a “Catalytic” Cosolvent, N,N-Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch

By Yang, Jeffrey C.; Niu, Dawen; Karsten, Bram P.; Lima, Fabio; Buchwald, Stephen L.

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Published on CMKC

10 May 2024

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.

Journal

Angewandte Chemie International Edition. Volume 55, 2016, 2531-2535

DOI

10.1002/anie.201509922

Type of publication

Peer-reviewed journal

Affiliations

Massachusetts Institute of Technology

Article Classification

Research Article

Classification Areas

API