Ni-Catalyzed C–H
Functionalization in the Formation
of a Complex Heterocycle: Synthesis of the Potent JAK2 Inhibitor BMS-911543

Fitzgerald, Monica
A; Soltani, Omid; Wei, Carolyn; Skliar, Dimitri; Zheng, Bin; Li, Jun; Albrecht, Jacob; Schmidt, Michael; Mahoney, Michelle; Fox, Richard J.; Tran, Kristy; Zhu, Keming; Eastgate, Martin D.

doi:10.1021/acs.joc.5b00572.s001

jo5b00572_si_001.pdf (730.93 kB)

Ni-Catalyzed C–H Functionalization in the Formation of a Complex Heterocycle: Synthesis of the Potent JAK2 Inhibitor BMS-911543

journal contribution

posted on 2015-06-19, 00:00 authored by Monica A Fitzgerald, Omid Soltani, Carolyn Wei, Dimitri Skliar, Bin Zheng, Jun Li, Jacob Albrecht, Michael Schmidt, Michelle Mahoney, Richard J. Fox, Kristy Tran, Keming Zhu, Martin D. Eastgate

BMS-911543 is a complex pyrrolopyridine investigated as a potential treatment for myeloproliferative disorders. The development of a short and efficient synthesis of this molecule is described. During the course of our studies, a Ni-mediated C–N bond formation was invented, which enabled the rapid construction of the highly substituted 2-aminopyridine core. The synthesis of this complex, nitrogen-rich heterocycle was accomplished in only eight steps starting from readily available materials.