Methanol → N-(1H-Indol-4yl)-N'-methyl-N-phenyl-ethane-1,2-diamine

温度

50 °C

To a room temperature solution of N-(1H-indol-4-yl)-2-methylamino-N-phenyl-acetamide XXIV (122 mg, crude 0.435 mmol) in THF (6 ml) was added BH3.SMe2 (2 M in THF, 653 μl, 1.31 mmol). The mixture was stirred at room temperature for 2 hours, at 50° C. for 2 hours, and at reflux for 2 hours. The resulting mixture was then kept at −18° C. for 5 days. It was then warmed at room temperature and BH3.SMe2 (2M in THF, 653 μl, 1.31 mmol) was added. The mixture was refluxed for 45 minutes, cooled to 0° C., and MeOH (1.5 ml) and HCl (conc., 9 drops) were added. The mixture was stirred at 0° C. for 5 minutes, at room temperature for 1 hour and at 50° C. for 2 hours. The reaction mixture was cooled to room temperature and diluted a saturated solution of NaHCO3 and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH/NH4OH). The chromatographed material was dissolved in p-xylene (9 ml) and Pd/C (5%, 14 mg) was added. The reaction mixture was refluxed for 3 hours, cooled to room temperature, and filtered through a celite pad with the aid of hot methanol. The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH) affording N-(1H-indol-4yl)-N′-methyl-N-phenyl-ethane-1,2-diamine XXV (8 mg, light brown oil). MS (M+H)=266.

1. temperatureat reflux for 2 hours
2. waitThe resulting mixture was then kept at −18° C. for 5 days
3. temperatureIt was then warmed at room temperature
4. temperatureThe mixture was refluxed for 45 minutes
5. temperaturecooled to 0° C.
6. stirringThe mixture was stirred at 0° C. for 5 minutes, at room temperature for 1 hour and at 50° C. for 2 hours
7. temperatureThe reaction mixture was cooled to room temperature
8. extractionThe aqueous layer was extracted with EtOAc
9. dry with materialThe combined organic layers were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. custompurified via flash chromatography (DCM/MeOH/NH4OH)
13. dissolutionThe chromatographed material was dissolved in p-xylene (9 ml)
14. additionPd/C (5%, 14 mg) was added
15. temperatureThe reaction mixture was refluxed for 3 hours
16. temperaturecooled to room temperature
17. filtrationfiltered through a celite pad with the aid of hot methanol
18. concentrationThe filtrate was concentrated
19. custompurified via flash chromatography (DCM/MeOH/NH4OH)

ORDレコード

ord-391a5f65f9d542419be1c39f2768cebe

出典データセット

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07803830B2