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The synthesis of 3-halo-2-(hetero)arylthieno[2,3-6]pyri-dines and 3-halo-2-(hetero)arylthieno[3,2-6]pyridines has been per-formed 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 bro-mo(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. [ABSTRACT FROM AUTHOR]