Carbazole → 2-[1-Methyl-3-oxo-3-(3-pyridyl)-propenylamino]-3-[4-(2-carbazolylethoxy)-phenyl]-propionic acid

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Reaction Steps

To a solution of 2-(1-methyl-3-oxo-3-(3-pyridyl)-propenylamino)-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (0.22 g, 0.49 mmol) and carbazole (0.082 g, 0.49 mmol) in benzene (10 ml) is added tetrabutyl ammonium bromide (0.08 g) and 50% NaOH aqueous solution (0.084 g, 1.08 mmol), then the mixture is heated to reflux for 10 h. After cooled, benzene (30 ml) is added, and the mixture is washed with water(3×30 ml). Then the solvent is evaporated under a vacuum. The crude product is purified by silica gel chromatography using CHCl3/MeOH (4:1) as eluent to give the title compound (0.04 g, 16%). HRMS calcd for C32H29N3O4: 519.6001. Found: 519.6003. MA calcd for C32H29N3O4: C, 73.97%; H, 5.63%; N, 8.09%. Found: C, 73.84%; H, 5.65%; N, 8.11%.

Provenance & Evidence