An Improved Synthesis of 3-Methyl-5-hydroxy Protected Indoles

Abstract

The synthesis of 3-methyl-5-alkoxy indoles 14 and 15 was accomplished through the use of DIBALH to effect the reductive-cyclization of an amino-nitrile intermediate. The mild conditions used to induce cyclization allowed for the use of a benzyl protecting groups which is normally sensitive to palladium catalyzed reducing conditions.