Water → HCID 25007649, compound

Participants

Reaction Steps

To a solution of 1-(2,4-dimethoxyphenyl)-N-{[4-fluoro-5-(2-fluoropyridin-3-yl)-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}-N-methylmethanamine (2.75 g) in tetrahydrofuran (10 mL) was added a solution of 1-chloroethyl chlorocarbonate (781 mg) in tetrahydrofuran (2 mL) at 0° C., and the mixture was stirred for 15 min. Triethylamine (2.3 mL) was added and the obtained mixture was refluxed for 16 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Ethanol (12 mL) was added to the residue, and the mixture was refluxed for 1.5 hr, and concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate:methanol=9:1→1:1) to give the title compound as a yellow solid (yield 1.46 g, 75%).

Provenance & Evidence