Synthesis of 2-Aryl Indoles

NU 2014-030

Inventors

Michael Todd Hovey Jr.

Christopher Thomas Check

Karl A Scheidt*

Short Description

New method for synthesis of indoles without employing harsh conditions or transition metal catalysts

Abstract

Northwestern University researchers have developed a novel method for synthesis of indole compounds for medicinal purposes. Several drugs currently on the market have an indole core, so improving methods for production is a high priority. Presently, synthesis of indoles is costly and complex. Transition metal catalysts are used, which have to be removed from the final product before the compounds can be tested for activity. In addition, current indole-generating reactions proceed under harsh conditions, which are inconvenient and can be hazardous. The novel synthetic method invented by the Scheidt group removes the need for transition metal catalysts and ensures that mild reaction conditions can be used. Finally, reaction products are produced in high yields, which will make this inventive approach the method of choice for indole synthesis in the future and enable many more drug discovery efforts.

Applications

• Production of 2-aryl indoles
• Production of C2 and C3 substituted indole compounds
• Drug discovery

Advantages

• Mild reaction conditions
• High yield
• Wide functional group and substrate scope
• Difficult catalysts (transition metals) are not necessary

Publications

Hovey M, Check C, Sipher A, and Scheidt K (2014) N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles . Angewandte Chemie. 36(1): 9757-9761.

IP Status

A provisional US patent application has been filed.