反应详情

温度

40 °C

4-Allyl-5-(benzyloxy)-1H-indole (368.7 mg, 1.40 mmol) (Example 58) was dissolved in anhydrous DMF (12 mL) under an inert atmosphere, and the reaction mixture was cooled in an ice-water bath. Sodium hydride (60% in mineral oil) (181 mg, 1.68 mmol) was added, and the reaction mixture was stirred for an additional 30 min. Methyl iodide (278 mg, 1.96 mmol) was added and stirring at rt was continued for 30 min. The reaction mixture was heated to 40° C. for 12 h, cooled to rt, and water (10 drops) was added. The reaction mixture was concentrated under reduced pressure, after which water was added, and the aqueous phase was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:15) gave 259 mg (67%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 3.72 (m, 5H), 4.98 (d, 1H), 5.07 (d, 1H), 5.12 (s, 2H), 6.06 (m, 1H), 6.47 (s, 1H), 7.00 (d, 1H), 7.03 (s, 1H), 7.12 (d, 1H), 7.31 (m, 1H), 7.39 (m, 2H), 7.48 (m, 2H).

1. temperaturethe reaction mixture was cooled in an ice-water bath
2. stirringstirring at rt
3. waitwas continued for 30 min
4. temperaturecooled to rt
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. additionafter which water was added
7. extractionthe aqueous phase was extracted with EtOAc (2×)
8. dry with materialThe combined organic phases were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:15)