合成路线1

Reduction of methyl 4-formyl-3-nitrobenzoate (XIII) by means of Fe and HCl in EtOH, followed by Friedländer condensation of the resulting aminoaldehyde with acetophenone (XIV) in the presence of KOH at 95 °C, and treatment with HCl, yields 2-phenylquinoline-7-carboxylic acid hydrochloride (XV). Reduction of acid (XV) with LiAlH4 in THF gives alcohol (XVI), which is then oxidized by means of MnO2 in CHCl3 to give 2-phenylquinoline-7-carbaldehyde (XVII). Coupling of carbaldehyde (XVII) with the metalated derivative of 2-chloropyrazine (XVIII) in the presence LTMP (prepared from BuLi and TMP) in THF yields the diaryl carbinol (XIX), which is then subjected to Mitsunobu reaction with phthalimide (XX) in the presence of PS-PPh3 and DIAD in THF to provide the N-substituted phthalimide (XXI). Hydrazinolysis of phthalimide (XXI) with NH2NH2 in EtOH/CH2Cl2 then affords amine (I).
Alternatively, carbaldehyde (XVII) can be prepared by arylation of 7-methylquinoline (XXII) with phenyl lithium in THF, followed by air oxidation to produce 7-methyl-2-phenylquinoline (XXIII). Side chain oxidation of (XXIII) using SeO2 at 160 °C provides the target aldehyde (XVII) .