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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2209173Generated: October 31, 2026

Cesium carbonate → (R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one

https://huagongshe.com/reaction/2209173

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant5-Bromo-1-methylbenzimidazol-7-olHCID 117843100—
Reactant(S)-1-((R)-5-oxo-1-((R)-1-phenylethyl)pyrrolidin-3-yl)ethyl methanesulfonateHCID 117843588—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product(R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-oneHCID 117843027—

Reaction Conditions

Temperature90 °C

Reaction Steps

To a solution of 5-bromo-1-methyl-1H-benzo[d]imidazol-7-ol (30 mgs, 0.124 mmol) in DMF (3 mL) was added (S)-1-((R)-5-oxo-1-((R)-1-phenylethyl)pyrrolidin-3-yl)ethyl methanesulfonate 1.17 (60 mgs, 0.193 mmol) and Cs2CO3 (69 mgs, 0.212 mmol) and the reaction mixture was heated at 90° C. for 1 h. The reaction mixture was then diluted with ethylacetate and washed with water (3×), brine and dried over anhydrous magnesium sulfate. Filtration, followed by concentration gave (R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one, which was used for next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09376441B2
Source datasetuspto-grants-2016_06
ORD IDord-2f9047b114a648c88c3a3d570305c3bd
Source noteuspto-grants-2016_06