1072105-05-5Relevant articles and documents
Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity
Vantourout, Julien C.,Miras, Haralampos N.,Isidro-Llobet, Albert,Sproules, Stephen,Watson, Allan J. B.
, p. 4769 - 4779 (2017)
We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.
A flow-based synthesis of Imatinib: The API of Gleevec
Hopkin, Mark D.,Baxendale, Ian R.,Ley, Steven V.
, p. 2450 - 2452 (2010)
A concise, flow-based synthesis of Imatinib, a compound used for the treatment of chronic myeloid leukaemia, is described whereby all steps are conducted in tubular flow coils or cartridges packed with reagents or scavengers to effect clean product formation. An in-line solvent switching procedure was developed enabling the procedure to be performed with limited manual handling of intermediates. The Royal Society of Chemistry.
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.
, p. 2531 - 2535 (2016/02/18)
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. 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.