Facile Synthesis of 2-(4-Hydroxybiphenyl-3-yl)-1H-indoles from Anilines and 5′-Bromo-2′-hydroxyacetophenone

Abstract

2-Arylindoles are attractive scaffolds because they are found in many pharmacologically active molecules. In this study, we describe the facile synthesis of diverse 2-(2-hydroxyphenyl)-1H-indoles from anilines and 5′-bromo-2′-hydroxyacetophenone in two steps using palladium-catalyzed indole cyclization as a key reaction. The indole cyclization was primarily controlled by the substituent properties of anilines. Suzuki-coupling reactions of 2-(5′-bromo-2′-hydroxyphenyl)-1H-indoles with arylboronic acids provided the corresponding 2-(4-hydroxybiphenyl-3-yl)-1H-indoles in moderate yield.

GRAPHICAL ABSTRACT

Keywords:

• 2-Arylindoles
• 2-(4-hydroxybiphenyl-3-yl)-1H-indoles
• indole cyclization

ACKNOWLEDGMENT

The authors are grateful to the Korea University College of Pharmacy for providing the necessary facilities.

SUPPORTING INFORMATION

Experimental data for compounds 1–24 can be accessed on the publisher’s website.