反应详情

To a solution of 6-formyl indole (Example 29a) (0.63 g, 4.3 mmol) in dry DMF (20 ml) was added sodium hydride (60% dispersion in oil) (0.22 g, 5.5 mmol) portionwise over 5 minutes with stirring. The reaction mixture was stirred for a further 20 minutes, then solid 3-[2(E)-(7-chloroquinolin-2-yl)ethenyl]benzyl chloride (Example 14b) (1.7 g, 5.4 mmol) was added portionwise over 5 minutes, and the reaction mixture left to stir for 18 hours. The reaction was quenched with water, extracted into ethyl acetate, the combined organic extracts washed with water, then brine, dried, filtered and evaporated in vacuo. The crude solid was purified by flash chromatography on silica, eluting with 30% diethyl ether in hexane to give a pale yellow solid.

1. stirringThe reaction mixture was stirred for a further 20 minutes
2. waitthe reaction mixture left
3. stirringto stir for 18 hours
4. customThe reaction was quenched with water
5. extractionextracted into ethyl acetate
6. washthe combined organic extracts washed with water
7. dry with materialbrine, dried
8. filtrationfiltered
9. customevaporated in vacuo
10. customThe crude solid was purified by flash chromatography on silica
11. washeluting with 30% diethyl ether in hexane
12. customto give a pale yellow solid