Shared posts

15 Jan 01:56

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

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

Abstract

A general, efficient method for C[BOND]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.

Thumbnail image of graphical abstract

Going with the flow: A general flow method developed for C[BOND]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.

09 Jan 06:43

Copper-Catalyzed Coupling of Oxime Acetates with Isothiocyanates: A Strategy for 2-Aminothiazoles

by Xiaodong Tang, Zhongzhi Zhu, Chaorong Qi, Wanqing Wu and Huanfeng Jiang

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.5b03188