合成路线1

Coupling between 4-bromophenol (I) and 1-adamantanol (II) in the presence of H2SO4 affords the adamantanyl phenol (III), which is further protected as the silyl ether (IV) by means of t-butyldimethylsilyl chloride and DMAP. Addition of triisopropyl borate to the organolithium derivative of (IV) gives rise, after aqueous quenching, to the boronic acid (V). Then, Suzuki coupling of boronic acid (V) with 6-bromopyridine-3-carbaldehyde (VI) furnishes the phenylpyridine adduct (VII). Desilylation of (VII) to provide phenol (VIII) is accomplished by treatment with tetrabutylammonium fluoride in THF. Finally, condensation of pyridine aldehyde (VIII) with 2,4-thiazolidinedione (IX) under Knoevenagel conditions provides the target compound