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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1174059Generated: November 1, 2026

1-(2-Allyloxy-5-iodo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → 2'-(2-Allyloxy-5-iodo-phenyl)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

https://huagongshe.com/reaction/1174059

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-(2-Allyloxy-5-iodo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 72325794—
ReactantZ-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-oneHCID 86615089—
SolventTolueneHCID 1140—
Product2'-(2-Allyloxy-5-iodo-phenyl)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilaneHCID 7770016944.4%

Reaction Steps

In a manner similar to the method described in example 1d, E/Z-6-chloro-3-(3-chlorobenzylidene)-1-(2-trimethylsilanyl-ethoxymethyl-1,3-dihydro-indole-2-one (6 g, 15 mmol) prepared in example 1b was reacted with 1-(2-allyloxy-5-iodo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (26 g, 65 mmol) prepared in example 18b in toluene (100 mL) to give racemic (2′R, 3R, 4′S)-2′-(2-allyloxy-5-iodo-phenyl)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxo spiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a white foam (5 g, 44%)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07834179B2
Source datasetuspto-grants-2010_11
ORD IDord-716689704a4144f2ae6b0c6316882f24
Source noteuspto-grants-2010_11