2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → HCID 90031343, compound

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Reaction Steps

To a solution of N1-(2-(1H-indol-2-yl)ethyl)-2-fluorobenzene-1,4-diamine (2.09 g, 7.76 mmol) in CH2Cl2 (30 mL) was added trimethylaluminium (19.4 mL, 38.8 mmol, 2 M in toluene) slowly. The mixture was stirred at rt for 1 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (2.44 g, 15.52 mmol) in CH2Cl2 (10 mL). The reaction mixture was stirred further at rt for 72 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×2). The combined organic phases were washed with brine (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (0.95 g, 33%). The compound was characterized by the following spectroscopic data:

Provenance & Evidence