Regioselective Diversification of Aminopyrazoles via Ir‐Catalyzed C─H Borylation

Aminopyrazoles are privileged molecular cores in drug design that present unique synthetic challenges, particularly when developing direct, site‐selective transition metal‐catalyzed C─H functionalization. Specifically, differentiating between C─H sites while contending with the reactivity of the amine and azinyl components is an unresolved challenge. Here, we describe strategies for the regioselective functionalization of 3‐ and 5‐aminopyrazoles through Ir‐catalyzed C─H borylation, exploiting the interplay between intrinsic reactivities and directing effects that influence C─H activation. The resulting borylated adducts can readily be elaborated to provide a range of arylated aminopyrazoles. Collectively, these studies constitute a general and readily adaptable blueprint for selectively generating isomeric aminopyrazole pharmacophores with tunable product distributions.