1448146-99-3Relevant articles and documents
Regiocontrolled SNAr reaction on 2,3-dihalopyridines with NaSMe to obtain bromo(methylthio)pyridines as key precursors of 3-halo-2-(hetero) arylthieno[2,3- b ]pyridines and thieno[3,2- b ]pyridines
Begouin, Agathe,Peixoto, Daniela,Queiroz, Maria-Joao R. P.
, p. 1489 - 1496 (2013/07/19)
The synthesis of 3-halo-2-(hetero)arylthieno[2,3-b]pyridines and 3-halo-2-(hetero)arylthieno[3,2-b]pyridines has been performed through a three-step methodology from 3-bromo-2-chloropyridine or 2-bromo-3- fluoropyridine, respectively. The key step of this methodology is the formation of the required bromo(methylthio)pyridines by a regiocontrolled nucleophilic aromatic substitution (SNAr) with sodium methanethiolate (NaSMe). Then, the Sonogashira coupling with (hetero)arylalkynes followed by a halocyclization with bromine or iodine, afforded the expected 3-halo-2-(hetero)arylthienopyridines.