Use of a "Catalytic" Cosolvent, N, N‐Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch. Issue 7 (12th January 2016)

• Record Type: Journal Article
• Authors: Yang, Jeffrey C.; Niu, Dawen; Karsten, Bram P.; Lima, Fabio; Buchwald, Stephen L.
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 7(2016)
• Page Start: 2531
• Page End: 2535
• Publication Date: 2016-01-12
• Subjects: biaryls -- cross-coupling -- flow chemistry -- palladium -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201509922
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Going with the flow : A general flow method developed for C−N cross‐coupling using N, N ‐dimethyloctanamide as a catalytic cosolvent was integrated into a two‐step sequence which converted phenols into biarylamines via either triflates or tosylates. It was applied to a three‐step synthesis of imatinib, the API of Gleevec, in good yield without the need of solvent switches.