Protected Indazole Boronic Acid Pinacolyl Esters: Facile Syntheses and Studies of Reactivities in Suzuki-Miyaura Cross-Coupling and Hydroxydeboronation Reactions

Autor:	Valérie Collot, François Crestey, Silvia Stiebing, Sylvain Rault, Elodie Lohou
Rok vydání:	2009
Předmět:	Solvent Tryptamine chemistry.chemical_compound Indazole chemistry Aryl Organic Chemistry Halogen Protecting group Medicinal chemistry Boronic acid Coupling reaction
Zdroj:	Synlett. 2009:615-619
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0028-1087922
Popis:	The paper describes a rapid and efficient synthesis for the isolation of protected indazolylboronic esters. These com- pounds were synthesized by reaction between prepared protected haloindazoles and bis(pinacolato)diboron. The effects of solvent, temperature, reaction time, and the nature of halogen atom as well as protecting group were investigated. Additionaly, these com- pounds reacted either with aryl halides in a Suzuki-Miyaura cross- coupling reaction or with hydrogen peroxide in a hydroxydeborona- tion reaction showing the potential access to new aryl and hydroxy- indazole libraries. Our group has long been interested in the design and syn- thesis of new polyfunctionalized indazole libraries, 1 par- ticularly those derived from the 2-aza bioisosteres of tryptamine, serotonin, melatonin, or tryptophan. 2
Databáze:	OpenAIRE
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