反应详情

温度

80 °C

Under argon atmosphere, sodium carbonate (1000 mg) and tetrakis(triphenylphosphine)palladium (170 mg) were added to a mixture of (2-fluoro-3-formylphenyl)boronic acid (700 mg), tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (1000 mg), toluene (15 ml), EtOH (5 ml) and water (5 ml) followed by stirring at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, and CHCl3 and a saturated aqueous sodium hydrogen carbonate solution were then added thereto. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc). The purified product thus obtained was mixed with EtOH, and NaBH4 (120 mg) was added thereto, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and then EtOAc and water were added thereto. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain tert-butyl 4-[2-fluoro-3-(hydroxymethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate (637 mg).

1. concentrationThe reaction mixture was concentrated under reduced pressure, and CHCl3
2. additiona saturated aqueous sodium hydrogen carbonate solution were then added
3. dry with materialThe organic layer was dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)
6. customThe purified product thus obtained
7. additionwas added
8. stirringby stirring at room temperature for 30 minutes
9. concentrationThe reaction mixture was concentrated under reduced pressure
10. additionEtOAc and water were added
11. dry with materialThe organic layer was dried over Na2SO4
12. concentrationconcentrated under reduced pressure
13. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)