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.