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Highly substituted indole library synthesis by palladium-catalyzed coupling reactions in solution and on a solid support.

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.

SUBMITTER: Worlikar SA

PROVIDER: S-EPMC2760449 | biostudies-literature | 2009 Sep-Oct

REPOSITORIES: biostudies-literature

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Highly substituted indole library synthesis by palladium-catalyzed coupling reactions in solution and on a solid support.

Worlikar Shilpa A SA Neuenswander Benjamin B Lushington Gerald H GH Larock Richard C RC

Journal of combinatorial chemistry 20090901 5

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 bee ...[more]

PMID: 19746991

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