合成路线1

The reaction of 6-methoxybenzo[b]thiophene (I) with triisopropyl borate by means of BuLi in THF gives the boronic acid (II), which is condensed with 4-(methanesulfonyloxy)phenyl bromide (III) by means of sodium carbonate in toluene, yielding the intermediate (IV). The demethylation of (IV) with boron tribromide in dichloromethane affords phenol (V), which is protected with benzyl chloride (VI) and cesium carbonate to afford the benzyl ether (VII). The reduction of (VII) with LiAlH4 in THF provides the phenol (VIII), which is methylated with NaH and methyl iodide to the ether (IX). The bromination of (IX) with Br2 and NaHCO3 in CHCl3 affords the 3-bromo derivative (X), which is oxidized with H2O2 in TFA/dichloromethane to the sulfoxide (XI). The condensation of (XI) with 4-[2-(1-piperidinyl)ethoxy]phenol (XII) in basic medium gives the expected condensation product (XIII), which is reduced at the sulfinyl group to yield the protected compound (XIV). Finally, this compound is debenzylated by hydrogenation by means of ammonium formate over Pd/C in ethanol/ethyl acetate and converted to its hydrochloride salt by treatment with ethyl ether/HCl in ethyl acetate.