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

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...

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Veröffentlicht in:Organic & biomolecular chemistry 2017, Vol.15 (48), p.10200-10211
Hauptverfasser: Tomanová, Monika, Jedinák, Lukáš, Košař, Jan, Kvapil, Lubomír, Hradil, Pavel, Cankař, Petr
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Sprache:eng
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02373a