合成路线1

Lithiation of 2-bromo-4-fluoroanisole (I) produced the intermediate organolithium reagent (II), which was treated with trimethyl borate to yield, after acid hydrolysis, the arylboronic acid (III). Subsequent Suzuki coupling of (III) with methyl 2-bromo-5-nitrobenzoate (IV) in the presence of palladium catalyst afforded biphenyl (V). The methyl ester group of (V) was hydrolyzed with KOH to give acid (VI). This was converted to the acid chloride with SOCl2, and then cyclized to the benzocoumarin (VII) employing AlCl3. Reduction of the nitro group of (VII) by hydrogenation over Pd/C produced aniline (VIII). The required quinoline derivative (IX) was prepared by heating (VIII) with acetone and iodine in a pressure tube. Then, addition of butyllithium to the lactone function produced hemiacetal (X). This was finally reduced with triethylsilane in the presence of a protic or a Lewis acid to provide the title compound.