反应详情

温度

80 °C

Dissolve N-{2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-4-fluoro-N-methyl-benzenesulfonamide (0.160 g, 0.387 mmol) in DME (5 mL, previously degassed with nitrogen). Add 4-indole boronic acid (0.094 g, 0.581 mmol), 2N aqueous potassium carbonate (0.464 mL, 0.129 g, 0.930 mmol), and tetrakis(triphenylphosphine)palladium (0.022 g, 0.022 mmol). Stir the reaction mixture at 80° C. for 18 hr. Add fresh catalyst (0.015 g) and boronic acid (0.050 g). Stir an additional 8 hr. at 95° C. Cool to room temperature and concentrate to remove DME. Dilute with ethyl acetate and brine. Extract the aqueous layer with ethyl acetate. Combine the organic layers, dry over sodium sulfate, filter, and concentrate. Purify the resulting material by silica gel chromatography eluting with dichloromethane:methanol 94:6 to 90:10 to afford the title compound (0.031 g).

1. custompreviously degassed with nitrogen)
2. stirringStir an additional 8 hr
3. customat 95° C
4. temperatureCool to room temperature
5. concentrationconcentrate
6. customto remove DME
7. additionDilute with ethyl acetate and brine
8. extractionExtract the aqueous layer with ethyl acetate
9. dry with materialdry over sodium sulfate
10. filtrationfilter
11. concentrationconcentrate
12. customPurify the resulting material by silica gel chromatography
13. washeluting with dichloromethane:methanol 94:6 to 90:10