title: Rearrangement of 4-amino-3-halo-pyridines by nucleophilic aromatic substitution.
abstract: The reaction of 3-halo-4-aminopyridines with acyl chlorides and triethylamine is described. The pyridin-4-yl α-substituted acetamide products were obtained in moderate to high yields. The presented rearrangement reaction, in which the presumed N-acylated intermediate reacts intramolecularly via nucleophilic aromatic substitution, results in a formal two-carbon insertion.
authors.affiliation: Drug Discovery Program, Ontario Institute for Cancer Research, 101 College Street, MaRS Centre, South Tower, Toronto, ON M5G 0A3, Canada.
authors.forename: Matthäus
authors.initials: M
authors.lastname: Getlik
authors.forename: Brian J
authors.initials: BJ
authors.lastname: Wilson
authors.forename: M Monzur
authors.initials: MM
authors.lastname: Morshed
authors.forename: Iain D G
authors.initials: ID
authors.lastname: Watson
authors.forename: Doris
authors.initials: D
authors.lastname: Tang
authors.forename: Pandiaraju
authors.initials: P
authors.lastname: Subramanian
authors.forename: Rima
authors.initials: R
authors.lastname: Al-awar
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D005021:Ethylamines / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*
chemical_list: D000081:Acetamides; D005021:Ethylamines; D006843:Hydrocarbons, Chlorinated; D011725:Pyridines; C016162:triethylamine