The reductive alkylation of 4-(2-methoxyphenoxy)aniline (I) with pyridine-3-carboxaldehyde (II) in the presence of NaBH4 leads to the N-pyridylmethyl aniline adduct (III) (1). Alternatively, 4-bromoaniline (IV) is reductively alkylated with pyridine-3-carboxaldehyde (II) to produce (V). Subsequent copper-catalyzed bromide displacement of (V) with guaiacol (VI) affords intermediate (III) (2). Finally, acylation of amine (III) with 2,2,2-trifluoroethylsulfonyl chloride (VII) gives rise to the target sulfonamide (1,2).

Coupling of 2-methoxyphenol (I) with 3-fluoronitrobenzene (II) produced the diaryl ether (III). The nitro group of (III) was then reduced by catalytic hydrogenation over Raney-Ni, yielding aniline (IV). Reductive alkylation of (IV) with pyridine-3-carboxaldehyde (V) using NaBH4 furnished the secondary amine (VI). This was finally acylated with 2,2,2-trifluoroethylsulfonyl chloride to produce the title sufonamide.