Development of a Late-Stage Diversification Strategy for the 4- and 5‑Positions of 4,5,6-Trisubstituted Indazoles

Indazoles represent a privileged motif in drug discovery. However, the formation of highly substituted indazoles can require the execution of lengthy synthetic routes with minimal opportunities to introduce diversity. In this report, we disclose the development of a late-stage diversification strate...

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Bibliographic Details
Published in:Organic letters 2020-11, Vol.22 (22), p.9047-9052
Main Authors: Barber, Joyann S, Burtea, Alexander, Collins, Michael R, Tran-Dubé, Michelle, Patman, Ryan L, Scales, Stephanie, Smith, Graham, Spangler, Jillian E, Wang, Fen, Wang, Wei, Yang, Shouliang, Zhu, JinJiang, Montgomery, T. Patrick
Format: Article
Language:English
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Summary:Indazoles represent a privileged motif in drug discovery. However, the formation of highly substituted indazoles can require the execution of lengthy synthetic routes with minimal opportunities to introduce diversity. In this report, we disclose the development of a late-stage diversification strategy for the 4- and 5-positions of 4,5,6-trisubstituted indazoles. A regioselective C–H functionalization and subsequent nucleophilic aromatic substitution provide two sequential points of diversification. The synthetic sequence delivers rapid access to an array of 4,5,6-trisubstituted indazoles in only four steps from readily available starting materials.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03440