反应详情

温度

-78 °C

n-Butyllithium (1.7 mL, 4.17 mmol) (2.5 M in hexanes) was dropwise added to 1,3-dibromobenzene (0.504 mL, 4.17 mmol) in diethyl ether (25.00 mL) at −78° C. under argon. The resulting mixture was stirred at −78° C. for 1 h. Additional n-butyllithium (2.5 M in hexanes) (0.8 mL, 2.00 mmol) was added and the resulting reaction mixture was stirred at −78° C. for 30 min. N-((2-Cyano-3-fluorophenyl)(2-methoxypyridin-4-yl)methylene)-2-methylpropane-2-sulfinamide (1.500 g, 4.17 mmol) in diethyl ether (10.00 mL) was added dropwise and stirring was continued for 1 h at −78° C. Hydrochloric acid (25.04 mL, 12.52 mmol) (0.5 M in methanol) was added and the resulting reaction mixture was stirred at room temperature over night and concentrated in vacuo. The residue was partitioned between aqueous sodium bicarbonate (sat.) and ethyl acetate (×3). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. Purification by silica chromatography using 0% to 5% (3.5 M ammonia in methanol) in dichloromethane gave the title compound 0.812 g, (47% yield).

1. customthe resulting reaction mixture
2. stirringwas stirred at −78° C. for 30 min
3. stirringstirring
4. waitwas continued for 1 h at −78° C
5. customthe resulting reaction mixture
6. stirringwas stirred at room temperature over night
7. concentrationconcentrated in vacuo
8. customThe residue was partitioned between aqueous sodium bicarbonate (sat.) and ethyl acetate (×3)
9. dry with materialThe combined organic layers were dried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customPurification by silica chromatography