title: Ni-Catalyzed C-H Functionalization in the Formation of a Complex Heterocycle: Synthesis of the Potent JAK2 Inhibitor BMS-911543.
abstract: 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.
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Monica A
authors.initials: MA
authors.lastname: Fitzgerald
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Omid
authors.initials: O
authors.lastname: Soltani
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Carolyn
authors.initials: C
authors.lastname: Wei
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Dimitri
authors.initials: D
authors.lastname: Skliar
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Bin
authors.initials: B
authors.lastname: Zheng
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Jacob
authors.initials: J
authors.lastname: Albrecht
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Michael
authors.initials: M
authors.lastname: Schmidt
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Michelle
authors.initials: M
authors.lastname: Mahoney
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Fox
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Kristy
authors.initials: K
authors.lastname: Tran
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Keming
authors.initials: K
authors.lastname: Zhu
authors.affiliation: Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Martin D
authors.initials: MD
authors.lastname: Eastgate
mesh_terms: D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D053614:Janus Kinase 2 / Q000037:antagonists & inhibitors* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; C571029:N,N-dicyclopropyl-4-((1,5-dimethyl-1H-pyrazol-3-yl)amino)-6-ethyl-1-methyl-1,6-dihydroimidazo(4,5-d)pyrrolo(2,3b)pyridine-7-carboxamide; D009532:Nickel; D053614:Janus Kinase 2