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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 532112Generated: November 2, 2026

Trimethylsilyl iodide → (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

https://huagongshe.com/reaction/532112

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethylsilyl iodideHCID 85247—
ReactantApremilastHCID 11561674—
SolventDichloromethaneHCID 6344—
SolventSodium chloride; waterHCID 57417360—
Product(S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamideHCID 68088610—

Reaction Steps

To a stirred solution of (S)—N-{2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (1 mmol) in anhydrous CH2Cl2, is added iodotrimethylsilane (6 mmol). The mixture is stirred at room temperature for 24 hours. The reaction mixture is diluted with brine and is extracted with CH2Cl2. The CH2Cl2 is removed to give crude (S)—N-{-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide. The product is purified by recrystallization.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08853175B2
Source datasetuspto-grants-2014_10
ORD IDord-595bd32be902425597cbf3e4eee634d6
Source noteuspto-grants-2014_10