4-Bromobenzyl bromide → N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochloride

Participants

Reaction Steps

4-Methoxyphenylhydrazine hydrochloride is reacted with 4-bromobenzyl bromide in the presence of a base to provide N-(4-bromo-benzyl)-N-(4-methoxy-phenyl)-hydrazine hydrochloride. N-(4-bromo-benzyl)-N-(4-methoxy-phenyl)-hydrazine hydrochloride is reacted with 5-tert-butylsulfanyl-2,2-dimethyl-4-oxo-pentanoic acid alkyl esters of structure 2-4 (where R1 is C1-C6 alkyl) to provide 3-[1-(4-bromo-benzyl)-3-tert-butylsulfanyl-5-methoxy-1H-indol-2-yl]-2,2-dimethyl-propionic acid alkyl esters of structure 3-1. In one aspect, R1 is selected from methyl, ethyl, propyl, isopropyl, and butyl. In another aspect, R1 is methyl or ethyl. In another aspect, R1 is ethyl.

Provenance & Evidence