Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki–Miyaura coupling and iron-catalyzed reduction

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F17%3A73583744" target="_blank" >RIV/61989592:15110/17:73583744 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/17:73583744
Result on the web
<a href="http://pubs.rsc.org/en/content/articlepdf/2017/ob/c7ob02373a" target="_blank" >http://pubs.rsc.org/en/content/articlepdf/2017/ob/c7ob02373a</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c7ob02373a" target="_blank" >10.1039/c7ob02373a</a>

Result language
angličtina
Original language name
Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki–Miyaura coupling and iron-catalyzed reduction
Original language description
A general and efficient synthesis of 4-substituted-1H-pyrazole-3,5-diamines was developed to access derivatives with an aryl, heteroaryl, or styryl group, which are otherwise relatively difficult to prepare. The first step is based on the Suzuki–Miyaura cross-coupling reaction utilizing the XPhos Pd G2 precatalyst. The coupling reactions of 4-bromo-3,5-dinitro-1H-pyrazole with the electron-rich/deficient or sterically demanding boronic acids enabled the production of the corresponding dinitropyrazoles. The subsequent iron-catalyzed reduction of both nitro groups with hydrazine hydrate accomplished the synthesis. The additional demethylation of the 4-methoxystyryl derivative allowed the production of the carboanalog of CAN508 reported as a selective CDK9 inhibitor.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/LO1304" target="_blank" >LO1304: Support of suistainability of the Institute of Molecular and Translational Medicine</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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