合成路线1

2-Bromo-4-methylaniline (I) is converted to quinoline (II) upon condensation with glycerol under Skraup synthesis conditions. Radical bromination of (II) with N-bromosuccinimide affords the benzylic bromide (III), which is subsequently displaced with sodium methanesulfinate to yield sulfone (IV). Alkylation of sulfone (IV) with iodomethane in the presence of potassium tert-butoxide affords the dimethylated sulfone (V). This is then subjected to Suzuki coupling with the boronic acid (VI) to produce the 8-aryl quinoline (VII). Condensation of aldehyde (VII) with 4-(methylthio)aniline (VIII) generates imine (IX), to which methyllithium is added to furnish the alpha methylated amine (X). Acylation of amine (X) by 4-fluorobenzoyl chloride (XI) gives amide (XII). The methylsulfanyl group of (XII) is finally oxidized with oxone to the target bis-sulfone derivative.