Sodium hydride → Methyl 2-fluoro-3-(2-furan-3-yl-5-methoxyindol-1-ylmethyl)benzoate

To a solution of 2-furan-3-yl-5-methoxyindole (200 mg) in N,N-dimethylformamide (4.7 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 62 mg) under cooling with ice, and the mixture was stirred at room temperature for one hour. Then a solution of methyl 3-bromomethyl-2-fluorobenzoate (278 mg) in N,N-dimethylformamide (0.2 mL) was added, and the mixture was stirred at 80° C. for 15 hours. The reaction mixture was allowed to cool to ambient temperature. A saturated aqueous ammonium chloride solution-water (2/1) were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (72 mg).

1. temperatureunder cooling with ice
2. stirringthe mixture was stirred at 80° C. for 15 hours
3. temperatureto cool to ambient temperature
4. extractionthis resulting mixture was extracted with ethyl acetate
5. washThe organic layer was washed successively with water and saturated saline
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

ORD-Eintrag

ord-5b1b55b0c7df4cb9bbdc8ca0600bb995

Quelldatensatz

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08680120B2