合成路线1

The reaction of ethyl o-fluorophenylpyruvate (I) with p-chloro-N1-cyclopropylmethylphenylhydrazine (II) in refluxing ethanol gives the corresponding phenylhydrazone (III), which is cyclized by treating with HCl in hot ethanol yielding ethyl 1-cyclopropylmethyl-3-(2-fluorophenyl)-5-chloroindole-2-carboxylate (IV). The hydrolysis of (IV) with KOH in refluxing ethanol affords the corresponding free acid (V), which by treatment with refluxing SOCl2 is converted into the acyl chloride (VI). The reaction of (VI) with ammonia in water gives rise to the corresponding amide (VII), which by reduction with LiAlH4 in ether yields 1-cyclopropylmethyl-2-aminomethyl-3-(2-fluorophenyl)-5-chloroindole (VIII). Finally, this compound is treated with CrO3 in acetic acid. The reaction of amide (VII) with refluxing POCl3 yields the nitrile (IX), which can be reduced with LiAlH4 in ether affording the 2-aminomethyl compound (VIII) already obtained.