1393345-94-2Relevant academic research and scientific papers
Synthesis of 4-substituted pyrazole-3,5-diamines: Via Suzuki-Miyaura coupling and iron-catalyzed reduction
Tomanová, Monika,Jedinák, Luká?,Ko?a?, Jan,Kvapil, Lubomír,Hradil, Pavel,Canka?, Petr
, p. 10200 - 10211 (2017)
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.
