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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1728091Generated: October 30, 2026

Z-6-bromo-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

https://huagongshe.com/reaction/1728091

Reaction equation

Participants

RoleNameHCIDCharge
ReactantZ-6-bromo-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-oneHCID 68615044—
Reactant1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 70178504—
SolventTolueneHCID 1140—
Productracemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneHCID 7437069554%

Reaction Steps

In a manner similar to the method described in example 157b, E/Z-6-bromo-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole (0.4 g, 1.10 mmol) prepared in example 157a was reacted with 1-(5-fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 36a in toluene to give racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.3 g, 54%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07495007B2
Source datasetuspto-grants-2009_02
ORD IDord-df94cf49f8d34a59983998b3502f2b0c
Source noteuspto-grants-2009_02