合成路线1

Nitration of 2-amino-5-chloropyridine (I) in hot sulfuric acid afforded (II). Diazotization of amine (II) in the presence of Br2 and HBr produced the bromopyridine (III), and subsequent displacement of the bromide of (III) with cuprous cyanide at 150 C yielded the picolinonitrile (IV). Catalytic hydrogenation of the nitro group of (IV) in the presence of Raney-Ni gave rise to the amino amide (V), which was further hydrolyzed to acid (VI) using conc. HCl. Fischer esterification of acid (VI) with EtOH and H2SO4 furnished the ethyl ester (VII). Acid chloride (IX), prepared from m-phenoxyphenylacetic acid (VIII) and oxalyl chloride, was then condensed with amino ester (VII) to produce amide (X). Finally, cyclization of (X) in the presence of potassium hexamethyldisilazide yielded the title naphthyridinone.