Ammonium Chloride → HCID 59831665, compound

Participants

Reaction Steps

To a 0° C. suspension of MeNH2.HCl (97.9 mg, 1.45 mmol) in benzene (4 ml) was added Me3Al (2 M in toluene, 746 μl, 1.45 mmol). The mixture was stirred for 5 minutes and at room temperature for about 1.25 hours. A suspension of 3-(1H-indol-6-yl)-3-(1H-indol-3-yl)-propionic acid ethyl ester XXVII in benzene (15 ml) was added, and the resulting reaction mixture was stirred at reflux for 8 hours, and at room temperature for 16 hours. The reaction mixture was diluted with a saturated solution of NH4Cl (20 ml) and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH) affording 3-(1H-Indol-6-yl)-3-(1H-indol-3-yl)-N-methyl-propionamide XXVIII as a yellow oil (86 mg).

Provenance & Evidence