4-Bromobenzyl bromide → N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochloride
Reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>>[ClH:1].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[NH2:11])=[CH:15][CH:14]=1Participants
3
Procedure
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.
Sources & evidence
- ORD record
- ord-2d0dc28ed6c44f63a9094637a35dfa4c
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772495B2
Reaction notes
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