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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence