Application of Polystyrene Bound Ethoxymethyl (PEOM) Chloride in the Solid­-Phase Synthesis of Substituted 1-Methyl-1H-Indoles

Abstract

A novel linker for the solid-phase synthesis of substituted 1-methylindoles has been developed. The linker is stable under strong basic conditions and compatible with a broad range of chemical transformations as demonstrated by electrophilic and nucleophilic substitution reactions in the 2-position of the indole nucleus. Indoles are cleaved under reductive conditions by use of alane resulting in 1-methylindole derivatives. Sensitive functional groups in the indole moiety such as aldehydes, ketones, esters, imines, and amides are reduced simultaneously.

combinatorial chemistry - solid phase synthesis - derivatisation of indoles - nucleophilic aromatic substitution - reductive cleavage

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