反应详情

To a solution of 2-fluoro-N1-(3-morpholinopropyl)benzene-1,4-diamine (1.60 g, 6.23 mmol) in CH2Cl2 (30 mL) was added trimethylaluminum (22 mL, 44 mmol, 2 M in toluene) slowly at rt. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (1.98 g, 12.59 mmol) in CH2Cl2 (10 mL). The reaction was stirred at rt overnight, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a pale yellow solid (0.60 g, 27%). The compound was characterized by the following spectroscopic data:

1. stirringThe reaction was stirred at rt overnight
2. customquenched with saturated NH4Cl aqueous solution
3. extractionextracted with CH2Cl2 (50 mL×3)
4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)