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 in | Organic letters Vol. 18; no. 13; pp. 3218 - 3221 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
01.07.2016
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| Online Access | Get full text |
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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 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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| 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 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. 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. |
| Author | Basu, Kallol Ruck, Rebecca T Poirier, Marc |
| AuthorAffiliation | Department of Process & Analytical Chemistry Merck Research Laboratories |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27336404$$D View this record in MEDLINE/PubMed |
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| Copyright | Copyright © 2016 American Chemical Society |
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| DOI | 10.1021/acs.orglett.6b01456 |
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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... 3-(Hetero)arylindazoles are important motifs in several biologically active compounds. Mild and flexible palladium-mediated Negishi reaction conditions are... |
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| Title | Solution to the C3–Arylation of Indazoles: Development of a Scalable Method |
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