合成路线1

The synthesis of D-23129 is shown in Scheme 22750501a. Reaction of 4-nitroaniline (I) with chloroformic acid ethyl ester gives N-(4-nitrophenyl)carbamic acid ethyl ester (II), which is reduced with H2 over Pd/C in isopropyl acohol, yielding the corresponding 4-amino-derivative (III). This compound is transformed with phthalic acid anhydride in acetic acid into the phthalimide (IV), which is nitrated with fuming nitric acid to the nitro derivative (V). The phthalimide (V) is cleaved up with hydrazine hydrate in dimethoxyethane to the derivative (VI). Condensation of (VI) with 4-fluorobenzaldehyde in refluxing toluene gives the benzylidene aniline derivative (VII), which is reduced with sodium borohydride in DME/ethanol and subsequently with H2/Raney-nickel in dimethoxyethane, yielding D-23129.