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

Abstract 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...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2013-06, Vol.45 (11), p.1489-1496
Main Authors: Begouin, Agathe, Peixoto, Daniela, Queiroz, Maria-João R. P.
Format: Article
Language:English
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Summary:Abstract 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 (S N Ar) 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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1338442