Pyrrolidine → (1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

EDCxHCl (115 mg, 0.60 mmol), hydroxybenzothiazol (82 mg, 0.60 mmol), diisopropylethylamine (0.35 ml, 2.02 mmol) and pyrrolidine (0.05 mL, 0.60 mmol) were added to an ice-cooled suspension of 51e) (200 mg, 0.50 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 16 h and then diluted with dichloromethane (40 mL). The organic phase was successively washed with saturated ammonium chloride solution (2×50 mL), saturated sodium hydrogen carbonate solution (2×30 mL), water (30 mL), and brine (30 mL), dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography [100-200 mesh silica; 2% methanol in dichloromethane]. White solid. Yield: 65 mg (28% of theory). HPLC-MS (method 5): Rt=3.13 min; m/z [M+H]+=449.1

1. temperaturecooled
2. washThe organic phase was successively washed with saturated ammonium chloride solution (2×50 mL), saturated sodium hydrogen carbonate solution (2×30 mL), water (30 mL), and brine (30 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. customevaporated
5. customThe residue was purified by column chromatography [100-200 mesh silica; 2% methanol in dichloromethane]

ORD 기록

ord-87f2220d03154137b30b68dade8f739e

출처 데이터셋

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09315490B2