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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 928782Generated: November 1, 2026

Sodium Methoxide → (4-Chloro-2-methoxy-8-methyl-3-(4-(methylsulfonyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone

https://huagongshe.com/reaction/928782

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium MethoxideHCID 10942334—
Reactant(2,4-dichloro-8-methyl-3-(4-(methylsulfonyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanoneHCID 86715618—
SolventTolueneHCID 1140—
SolventDichloromethaneHCID 6344—
Product(4-Chloro-2-methoxy-8-methyl-3-(4-(methylsulfonyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanoneHCID 86715617—

Reaction Conditions

Temperature110 °C

Reaction Steps

A mixture of (2,4-dichloro-8-methyl-3-(4-(methylsulfonyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone (1.1 g, 2.15 mmol, Intermediate 40: step d) and dry sodium methoxide (0.58 g, 10.75 mmol) in toluene was heated in a sealed tube at 110° C. for 12 hours, cooled to room temperature, diluted with DCM, stirred for 30 minutes at room temperature and the resulting suspension filtered through Celite® rinsing several times with DCM. The solvents were removed under reduced pressure and the residue chromatographed (10% MeOH in DCM, gradient) to provide the title compound as a white solid after recrystallization from MeOH and drying under reduced pressure overnight.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290476B2
Source datasetuspto-grants-2016_03
ORD IDord-cc033dc2543d47879ff83624f840ffc5
Source noteuspto-grants-2016_03