HCID 178492258, compound → 5-methoxy-2-phenyl-1H-indole

Temperature

40 °C

A 500 mL round-bottom flask equipped with a stirrer bar was charged with (E)-4-methoxy-N-(1-phenylethylidene)aniline (50 mmol, 11.3 g), Pd(OAc)2 (0.56 g, 2.5 mmol, 5 mol %) and Cu(OAc)2 (18.2 g, 100 mmol, 2 equiv). The flask was evacuated and refilled with N2 for three times, followed by addition of DMSO (250 mL). The flask was sealed with a glass stopper and then the reaction mixture was stirred at 40° C. for 48 h. Upon cooling to room temperature, the reaction mixture was diluted with 150 mL of ethyl acetate and filtered through a pad of silica gel using 100 mL of ethyl acetate as additional eluent. The filtrate was washed with water (3×250 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization (EtOAc/hexane) to afford the title compound as an off-white solid (9.7 g, 87%). The product showed the same degree of analytical purity compared with that obtained by a small-scale reaction.

1. customA 500 mL round-bottom flask equipped with a stirrer bar
2. customThe flask was evacuated
3. additionrefilled with N2 for three times
4. additionfollowed by addition of DMSO (250 mL)
5. customThe flask was sealed with a glass stopper
6. temperatureUpon cooling to room temperature
7. additionthe reaction mixture was diluted with 150 mL of ethyl acetate
8. filtrationfiltered through a pad of silica gel using 100 mL of ethyl acetate as additional eluent
9. washThe filtrate was washed with water (3×250 mL)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by recrystallization (EtOAc/hexane)

ORD record

ord-8a499cea458f48b8bc041edbd43fbd9d

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334275B2