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Synthesis of Imidazo[4,5-b]pyridines and Imidazo[4,5-b]pyrazines by Palladium Catalyzed Amidation of 2-Chloro-3-amino-heterocycles

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Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, United States
[email protected]
Cite this: Org. Lett. 2012, 14, 7, 1764–1767
Publication Date (Web):March 13, 2012
https://doi.org/10.1021/ol300359s
Copyright © 2012 American Chemical Society
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    Abstract

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    A facile synthesis of imidazo[4,5-b]pyridines and -pyrazines is described using a Pd-catalyzed amide coupling reaction. This reaction provides quick access to products with substitution at N1 and C2. A model system relevant to the natural product pentosidine has been demonstrated, as well as the total synthesis of the mutagen 1-Me-5-PhIP.

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    30. Nathan T. Jui, Stephen L. Buchwald. Cascade Palladium Catalysis: A Predictable and Selectable Regiocontrolled Synthesis of N -Arylbenzimidazoles. Angewandte Chemie International Edition 2013, 52 (44) , 11624-11627. https://doi.org/10.1002/anie.201306007
    31. Jitender Bariwal, Erik Van der Eycken. C–N bond forming cross-coupling reactions: an overview. Chemical Society Reviews 2013, 42 (24) , 9283. https://doi.org/10.1039/c3cs60228a
    32. Jonathan Macdonald, Victoria Oldfield, Vassilios Bavetsias, Julian Blagg. Regioselective C2-arylation of imidazo[4,5-b]pyridines. Organic & Biomolecular Chemistry 2013, 11 (14) , 2335. https://doi.org/10.1039/c3ob27477b
    33. Adam J. Rosenberg, Theresa M. Williams, Abraham J. Jordan, Daniel A. Clark. Synthesis of 2-amino-imidazo[4,5-b]pyridines. Organic & Biomolecular Chemistry 2013, 11 (18) , 3064. https://doi.org/10.1039/c3ob40413g
    34. Yuan-Yuan Xing, Chuanxiang Liu, Fanhong Wu. Efficient synthesis of substituted imidazo[4,5-b]pyridines. Heterocyclic Communications 2013, 19 (5) https://doi.org/10.1515/hc-2013-0059
    35. Adam J. Rosenberg, Jinbo Zhao, Daniel A. Clark. ChemInform Abstract: Synthesis of Imidazo[4,5-b]pyridines and Imidazo[4,5-b]pyrazines by Palladium- Catalyzed Amidation of 2-Chloro-3-aminoheterocycles.. ChemInform 2012, 43 (31) , no-no. https://doi.org/10.1002/chin.201231126
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