Solution to the C-3-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 Lion and...

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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 WASHINGTON Amer Chemical Soc 01.07.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACIDS
ARYLATION
EFFICIENT SYNTHESIS
PROTOCOL
C-3
1H-INDAZOLES
ARYL
INHIBITORS
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Abstract 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 Lion and subsequent transmetalation. The methodology Zn-species are readily obtained via regioselective deprotonatolerates 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.
AbstractList 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 Lion and subsequent transmetalation. The methodology Zn-species are readily obtained via regioselective deprotonatolerates 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.
Author Ruck, Rebecca T.
Basu, Kallol
Poirier, Marc
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  givenname: Rebecca T.
  surname: Ruck
  fullname: Ruck, Rebecca T.
  organization: Merck Res Labs, Dept Proc & Analyt Chem, Rahway, NJ 07065 USA
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Keywords ACIDS
ARYLATION
EFFICIENT SYNTHESIS
PROTOCOL
C-3
1H-INDAZOLES
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Snippet 3-(Hetero)arylindazoles are important motifs in several biologically active compounds. Mild and flexible palladium-mediated Negishi reaction conditions are...
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Physical Sciences
Science & Technology
Title Solution to the C-3-Arylation of Indazoles: Development of a Scalable Method
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