Sodium hydride → HCID 18351578, compound

Temperature

0 °C

Under argon atmosphere, NaH (283 mg) was added to 4-methoxyindole (516 mg) in DMF (10 ml) and the mixture was stirred at 0° C. for 15 minutes. To this mixture, 2-tetrahydropyranyloxy-1-bromoethane (890 mg) was added and the mixture was gradually heated to room temperature, followed by stirring the mixture at room temperature for 90 minutes. The reaction mixture was added to saturated aqueous NH4Cl solution (5 ml) cooled at 0° C. to stop the reaction, and the resultant was extracted with ethyl acetate (3×10 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure. The obtained oil was transferred to a reaction vessel and dissolved in methanol (10 ml), followed by cooling the obtained solution to 0° C. To this solution, 1N hydrochloric acid (1 ml) was added and the solution was stirred at 0° C. for 2 hours. After removing the solvent under reduced pressure, water (5 ml) was added and the resultant was extracted with ethyl acetate (3×20 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (547 mg, yield: 82%).

1. temperaturethe mixture was gradually heated to room temperature
2. stirringby stirring the mixture at room temperature for 90 minutes
3. temperaturecooled at 0° C.
4. customthe reaction
5. extractionthe resultant was extracted with ethyl acetate (3×10 ml)
6. washThe obtained organic layers were washed with saturated brine
7. dry with materialdried over sodium sulfate
8. customAfter removing solids
9. filtrationby filtration
10. customthe solvent was removed under reduced pressure
11. customThe obtained oil was transferred to a reaction vessel
12. dissolutiondissolved in methanol (10 ml)
13. temperatureby cooling the obtained solution to 0° C
14. additionTo this solution, 1N hydrochloric acid (1 ml) was added
15. stirringthe solution was stirred at 0° C. for 2 hours
16. customAfter removing the solvent under reduced pressure, water (5 ml)
17. additionwas added
18. extractionthe resultant was extracted with ethyl acetate (3×20 ml)
19. washThe obtained organic layers were washed with saturated brine
20. dry with materialdried over sodium sulfate
21. customAfter removing solids
22. filtrationby filtration
23. customthe solvent was removed under reduced pressure
24. customthe obtained crude product
25. customwas purified by silica gel column chromatography

ORD record

ord-b4703f57391143c6898692dc75408f0f

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06323235B1