Cyclization of bromophenol (I) with 1-hexyne (II) in the presence of Pd (0) and CuI catalysts produced benzofuran (III). Then, oxidation of the aldehyde function of (III) with sodium chlorite provided carboxylic acid (IV). An alternative route to the intermediate (IV) consisted of a palladium/copper-catalyzed cyclization of bromophenol (V) with 1-hexyne (II), followed by basic hydrolysis of the resulting benzofuran methyl ester (VI). Treatment of carboxylic acid (IV) with oxalyl chloride yielded the corresponding acid chloride (VII), which was finally condensed with 4-amino-3,5-dichloropyridine (VIII) in the presence of NaEt2AlH2 to furnish the target amide.