Highly Substituted Indole Library Synthesis by Palladium-Catalyzed Coupling Reactions in Solution and on a Solid Support
- 15 July 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Combinatorial Chemistry
- Vol. 11 (5) , 875-879
Abstract
3-Iodoindoles have been synthesized by the iodocyclization of N,N-dialkyl-o-(1-alkynyl)anilines, obtained by the Pd/Cu catalyzed coupling of terminal acetylenes with N,N-dialkyl-o-iodoanilines. These 3-iodoindoles undergo palladium-catalyzed Sonogashira and Suzuki coupling reactions to yield 1,2,3-trisubstituted indoles. These reactions have been applied to parallel library synthesis utilizing commercially available terminal acetylenes and boronic acids. The aforementioned chemistry has also been carried out on a chlorinated Wang resin as a solid support, affording 1,2,3,5-tetrasubstituted indoles after cleavage from the support. A diverse 42-member library of highly substituted indoles has been synthesized.Keywords
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