title: Use of a "Catalytic" Cosolvent, N,N-Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch.
abstract: A general, efficient method for C-N cross-coupling has been developed using N,N-dimethyloctanamide as a catalytic cosolvent for biphasic continuous-flow applications. The described method was used to generate a variety of biarylamines and was integrated into a two-step sequence which converted phenols into biarylamines via either triflates or tosylates. Additionally, the method was applied to a three-step synthesis of imatinib, the API of Gleevec, in good yield without the need of solvent switches.
authors.affiliation: Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.
authors.forename: Jeffrey C
authors.initials: JC
authors.lastname: Yang
authors.affiliation: Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.
authors.forename: Dawen
authors.initials: D
authors.lastname: Niu
authors.affiliation: Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.
authors.forename: Bram P
authors.initials: BP
authors.lastname: Karsten
authors.affiliation: Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.
authors.forename: Fabio
authors.initials: F
authors.lastname: Lima
authors.affiliation: Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA. sbuchwal@mit.edu.
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D000068877:Imatinib Mesylate / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry*
chemical_list: D000577:Amides; D012997:Solvents; D000068877:Imatinib Mesylate
keywords: biaryls; cross-coupling; flow chemistry; palladium; synthetic methods