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Issue 48, 2017
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Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki–Miyaura coupling and iron-catalyzed reduction

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Abstract

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.

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

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Publication details

The article was received on 22 Sep 2017, accepted on 16 Nov 2017 and first published on 16 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02373A
Citation: Org. Biomol. Chem., 2017,15, 10200-10211
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    Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki–Miyaura coupling and iron-catalyzed reduction

    M. Tomanová, L. Jedinák, J. Košař, L. Kvapil, P. Hradil and P. Cankař, Org. Biomol. Chem., 2017, 15, 10200
    DOI: 10.1039/C7OB02373A

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