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Use of a “Catalytic” Cosolvent, N , N ‐Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch
Author(s) -
Yang Jeffrey C.,
Niu Dawen,
Karsten Bram P.,
Lima Fabio,
Buchwald Stephen L.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509922
Subject(s) - yield (engineering) , catalysis , solvent , combinatorial chemistry , continuous flow , imatinib , chemistry , coupling (piping) , phenols , organic chemistry , materials science , biochemical engineering , cancer research , engineering , biology , metallurgy , myeloid leukemia
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.