Sodium hydride → 1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole

To a solution of 5-methoxy-2-phenylindole (245 mg) in N,N-dimethylformamide (4.5 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 72 mg) under cooling with ice, and the mixture was stirred at room temperature for 75 minutes. Then a solution of 3-(benzyloxy)benzyl bromide (365 mg) in N,N-dimethylformamide (1 mL) was added dropwise, and the mixture was stirred at 80° C. for 15 hours. The reaction mixture was cooled to room temperature. A saturated aqueous ammonium chloride solution-water (2/1) were added and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography to obtain the title compound (202 mg).

1. temperatureunder cooling with ice
2. stirringthe mixture was stirred at 80° C. for 15 hours
3. temperatureThe reaction mixture was cooled to room temperature
4. extractionthis resulting mixture was extracted with ethyl acetate
5. washThe organic layer was washed with 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

ORD record

ord-a5c0a6f9c6fa4576879e49b61502fcdb

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680120B2