Oxidation of 4-nitro-2-methoxytoluene (I) by means of chromic anhydride and sulfuric acid in the presence of acetic anhydride gives rise to acylal (II), which is further hydrolyzed to aldehyde (III) under acidic conditions. Reaction of aldehyde (III) with tosylmethyl isocyanide produces the 5-aryl oxazole (IV). Reduction of the nitro group of (IV) by catalytic hydrogenation yields aniline (V). Then, electrophilic iodination of amine (V) with iodine and silver triflate furnishes the aryl iodide (VI).

6-Bromo-1-indanone (VII) is reduced to alcohol (VIII) employing NaBH4. After chlorination of (VIII) with SOCl2, the resultant alkyl chloride (IX) is displaced by heating with ethanolic dimethylamine in a sealed vessel to produce the (dimethylamino)indan (X). Palladium-catalyzed coupling of aryl bromide (X) with trimethylsilyl acetylene (XI) furnishes the silyl acetylene (XII), which is then desilylated to (XIII) with Bu4NF in THF. Finally, condensation between acetylene (XIII), aryl iodide (VI) and carbon monoxide in the presence of palladium catalyst leads to the title quinolone derivative. (1,2)

6-Bromo-1-indanone (VII) is reduced to alcohol (VIII) employing NaBH4. After chlorination of (VIII) with SOCl2, the resultant alkyl chloride (IX) is displaced by heating with ethanolic dimethylamine in a sealed vessel to produce the (dimethylamino)indan (X). Palladium-catalyzed coupling of aryl bromide (X) with trimethylsilyl acetylene (XI) furnishes the silyl acetylene (XII), which is then desilylated to (XIII) with Bu4NF in THF. Finally, condensation between acetylene (XIII), aryl iodide (VI) and carbon monoxide in the presence of palladium catalyst leads to the title quinolone derivative. (1,2)