反应详情

温度

100 °C

4-Fluoro-2-nitrobenzaldehyde (0.20 g, 1.2 mmol), N-(2-methoxyethyl)-2-morpholinoethylamine (1.2 g, 6.5 mmol) and DMSO (3.5 mL) were added and stirred at 100° C. for 3 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate). In a similar manner to Example 1, the obtained 4-[N-(2-methoxyethyl)-N-(2-morpholinoethyl)amino]-2-nitrobenzaldehyde was dissolved in methanol (8.0 mL) and the solution was added with (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.21 g, 0.62 mmol) and potassium carbonate (0.17 g, 1.3 mmol) followed by stirring at room temperature for 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=9/1) to obtain (E)-N-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}-N-(2-methoxyethyl)-2-morpholinoethylamine (45 mg, 20%).

1. extractionextracted with ethyl acetate
2. washThe organic layer was washed with water and saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customthe solvent was evaporated under reduced pressure
5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate)
6. dissolutionIn a similar manner to Example 1, the obtained 4-[N-(2-methoxyethyl)-N-(2-morpholinoethyl)amino]-2-nitrobenzaldehyde was dissolved in methanol (8.0 mL)
7. stirringby stirring at room temperature for 1 hour
8. extractionextracted with ethyl acetate
9. washThe organic layer was washed with water and saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under reduced pressure
12. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=9/1)