title: Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: efficient synthesis of poly-substituted 1,2,3-triazoles.
abstract: Reaction of 4-bromo-NH-1,2,3-triazoles 2 with alkyl halides in the presence of K(2)CO(3) in DMF produced the corresponding 2-substituted 4-bromo-1,2,3-triazoles 5 in a regioselective process. Subsequent Suzuki cross-coupling reaction of these bromides provided an efficient synthesis of 2,4,5-trisubstituted triazoles 3. In addition, reduction of the bromotriazoles by hydrogenation furnished an efficient synthesis of 2,4-disubstituted triazoles 8.
authors.affiliation: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, USA. xiao-jun.wang@boehringer-ingelheim.com
authors.forename: Xiao-Jun
authors.initials: XJ
authors.lastname: Wang
authors.forename: Kanwar
authors.initials: K
authors.lastname: Sidhu
authors.forename: Li
authors.initials: L
authors.lastname: Zhang
authors.forename: Scot
authors.initials: S
authors.lastname: Campbell
authors.forename: Nizar
authors.initials: N
authors.lastname: Haddad
authors.forename: Diana C
authors.initials: DC
authors.lastname: Reeves
authors.forename: Dhileepkumar
authors.initials: D
authors.lastname: Krishnamurthy
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006842:Hydrocarbons, Brominated; D014230:Triazoles