反应详情

To a stirred solution of 115 mg (0.60 mmol) of 4-phenylindole in 2 mL of tert-butyl methyl ether at room temperature was added 0.25 mL (0.75 mmol) of a 3 M solution of ethyl magnesium bromide in ether. The mixture stirred for 30 minutes and then 22.8 mg (0.12 mmol) of copper (I) iodide was added. After 30 minutes, a solution of 87.9 mg (0.30 mmol) of 2-trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine in 1 mL of tert-butyl methyl ether was added. After 18 hours, the reaction was quenched with 1 mL of ice-cold water. After 10 minutes, the reaction mixture was diluted with dichloromethane, filtered through CELITE® filter aid, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (12 g) eluting with ethyl acetate-hexanes (0-30% gradient) to afford an off-white solid. A second chromatography by preparative TLC eluting with ethyl acetate-hexanes (3:7) afforded 65 mg (22%) of the title compound as an off-white solid.

1. waitAfter 30 minutes
2. waitAfter 18 hours
3. customthe reaction was quenched with 1 mL of ice-cold water
4. waitAfter 10 minutes
5. additionthe reaction mixture was diluted with dichloromethane
6. filtrationfiltered through CELITE®
7. filtrationfilter aid
8. concentrationconcentrated in vacuo
9. customThe crude residue was purified by silica gel chromatography (12 g)
10. washeluting with ethyl acetate-hexanes (0-30% gradient)
11. customto afford an off-white solid
12. washA second chromatography by preparative TLC eluting with ethyl acetate-hexanes (3:7)