Solution to the C3–Arylation of Indazoles: Development of a Scalable Method

3-(Hetero)­arylindazoles are important motifs in several biologically active compounds. Mild and flexible palladium-mediated Negishi reaction conditions are reported for the introduction of (hetero)­aryl moieties at the 3-position of N(2)-SEM-protected indazoles in high yields. The requisite Zn-spec...

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Published inOrganic letters Vol. 18; no. 13; pp. 3218 - 3221
Main Authors Basu, Kallol, Poirier, Marc, Ruck, Rebecca T
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.07.2016
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Summary:3-(Hetero)­arylindazoles are important motifs in several biologically active compounds. Mild and flexible palladium-mediated Negishi reaction conditions are reported for the introduction of (hetero)­aryl moieties at the 3-position of N(2)-SEM-protected indazoles in high yields. The requisite Zn-species are readily obtained via regioselective deprotonation and subsequent transmetalation. The methodology tolerates a variety of functional groups on both coupling partners and has been extended to bis-haloarene and heteroarene coupling partners where the most reactive halogen reacts first, leaving the second halogen for subsequent functionalization.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01456