Ethyl acetate hexane → 4-(Dimethylamino)-N-(2-fluoro-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(1H-indol-6-yl)morpholine (0.393 g, 1.943 mmol), (E)-4-(dimethylamino)-N-(2-fluoro-3-(2-nitrovinyl)phenyl)benzamide (0.400 g, 1.215 mmol), and tris(trifluoromethylsulfonyloxy)ytterbium (0.075 g, 0.121 mmol) in acetonitrile (25 mL) was heated at 50° C. for 20 h. The acetonitrile was removed under vacuum. The residue was diluted with ethyl acetate (180 mL), washed with 10% NaHCO3 solution (2×40 mL) and brine (40 mL), and dried over anhydrous MgSO4. The desired product (0.412 g, 0.750 mmol, 61.8% yield) was isolated with ISCO (80 g silica gel, 30-80% ethyl acetate/hexane) as a pale yellow solid.

Provenance & Evidence