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

Milan Subedi, Jianbo Chen, Eunsol Kang, Kyung Im Kim, Youngjoo Byun

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented). 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.

Original languageEnglish (US)
Pages (from-to)1704-1709
Number of pages6
JournalSynthetic Communications
Volume45
Issue number14
DOIs
StatePublished - May 27 2015
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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