反应详情

To a solution of 5-bromo-2-nitropyridine (4.56 g, 22.4 mmol) and cesium carbonate (10.9 g, 33.6 mmol) in N,N-dimethylformamide (40 mL) was added dropwise a solution of 3-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide (6.92 g, 24.6 mmol) in N,N-dimethylformamide (20 mL) over 30 min, and the mixture was stirred at room temperature for 28 hr. Cesium carbonate (3.63 g, 11.2 mmol) was added to the reaction mixture, and the mixture was further stirred with heating at 60° C. for 15 hr. Water (200 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate-hexane mixture (1:1, 200 mL, 3×50 mL). The combined organic layer was washed with saturated brine (30 mL) and dried over anhydrous magnesium sulfate. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=90/10→50/50), and fractions containing the desired t product were concentrated under reduced pressure to give the title compound (6.01 g, 67%) as a yellow amorphous solid.

1. stirringthe mixture was further stirred
2. temperaturewith heating at 60° C. for 15 hr
3. extractionthe mixture was extracted with ethyl acetate-hexane mixture (1:1, 200 mL, 3×50 mL)
4. washThe combined organic layer was washed with saturated brine (30 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe insoluble material was removed by filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=90/10→50/50), and fractions
9. additioncontaining the desired t product
10. concentrationwere concentrated under reduced pressure