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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 389189Generated: October 31, 2026

Ethyl Acetate → HCID 58005143, compound

https://huagongshe.com/reaction/389189

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantCesium carbonateHCID 10796—
Reactant1-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 56590484—
ReactantHCID 57617105HCID 57617105—
SolventWaterHCID 962—
Solvent1-MethylpyrrolidineHCID 8454—
ProductHCID 58005143HCID 5800514392.1%

Reaction Conditions

Temperature45 °C

Reaction Steps

To a solution of the product from Step 4 (19.4 g, 41.7 mmol) and 6-bromo-7-methoxy-2-phenylquinolin-4(1H)-one (Step 3, 13.5 g, 40.9 mmol) in N-methylpyrrolidine (200 mL) was added cesium carbonate (20.0 g, 61.3 mmol). The reaction mixture was then heated at 45° C. with stirring for 15 hours and cooled to RT. The reaction mixture was poured into EtOAc and water, and the white solids removed by filtration. The layers were separated, and the organic phase washed with saturated aqueous NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica (gradient elution 10% to 50% EtOAc in hexanes) to give the title compound (21.0 g) as a pale yellow solid. LRMS (M+H)+ Calcd.: 557.1; found 557.3.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08377874B2
Source datasetuspto-grants-2013_02
ORD IDord-0f175e9a63e44596add6b0d783865b9b
Source noteuspto-grants-2013_02