1,2-Dichloroethane → HCID 67395396, compound

Participants

Reaction Conditions

Reaction Steps

To a solution (8 mL) of tert-butyl {[5-(2-fluoropyridin-3-yl)-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (214 mg) in 1,2-dichloroethane was added dropwise dimethyl sulfate (0.27 mL) under ice-cooling, and the mixture was stirred at 80° C. for 18 hr. The reaction mixture was cooled to room temperature, triethylamine (1.41 mL), acetic acid (0.94 mL) and ethanol (0.94 mL) were added and the mixture was heated under reflux for 2 hr. After cooling, the mixture was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: methanol-ethyl acetate=1:99→3:17) (basic TLC:Rf=0.2 (chloroform:methanol=10:1)) to give a free base of the title compound as a pale-yellow oil (yield 34.9 mg). The obtained free base (34.9 mg) was dissolved in ethyl acetate (1 mL) and ethanol (1 mL), and 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added. After stirring at room temperature for 2 hr, the reaction mixture was concentrated under reduced pressure. The residue was solidified with diisopropyl ether to give the title compound as a white solid (yield 20.8 mg, 11%).

Provenance & Evidence