Abstract
Formal homologation of sp(2)-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.
Highlights
In situ hydrolysis/Suzuki−Miyaura cross-coupling methods of BMIDA species have been developed.9i,k We have recently shown that the direct generation of BPin esters can be achieved by control of the solution speciation during cross-coupling of monoprotected diboron (BPin/BMIDA) systems (Scheme 1b).[13]
Suzuki−Miyaura Cross-Coupling with Haloaryl BMIDA Esters: (a) Retention of BMIDA; (b) Generation of BPin; (c) Formal Homologation of Boronic Acids multibond forming tandem reactions
We show the development of a formal boronic acid homologation protocol using B(OH)2/BMIDA diboron systems (Scheme 1c), enabled by control of the basic phase, and the utility of this process as a platform for diversity-oriented synthesis in the context of epigenetic drug discovery
Summary
Suzuki−Miyaura Cross-Coupling with Haloaryl BMIDA Esters: (a) Retention of BMIDA; (b) Generation of BPin; (c) Formal Homologation of Boronic Acids multibond forming tandem reactions. We show the development of a formal boronic acid homologation protocol using B(OH)2/BMIDA diboron systems (Scheme 1c), enabled by control of the basic phase, and the utility of this process as a platform for diversity-oriented synthesis in the context of epigenetic drug discovery.
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