反应详情

温度

120 °C

A mixture of 5-bromo-N2-methylpyridin-2,3-diamine (0.70 g), 2-ethylsulfanylbenzoic acid (0.66 g), WSC (0.80 g), HOBt (23 mg), and pyridine (20 ml) was stirred under reflux at 120° C. for 30 minutes. After the reaction mixture was allowed to stand overnight, the mixture was stirred under reflux at 120° C. for 9.5 hours again. Into the reaction mixture cooled to room temperature, water was poured under ice-cooling, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. A mixture of the resulting residue and acetic anhydride (7 ml) was stirred under reflux at 140° C. for 1 hour. Aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature to neutralize, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.60 g of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 42).

1. stirringthe mixture was stirred
2. temperatureunder reflux at 120° C. for 9.5 hours again
3. temperatureInto the reaction mixture cooled to room temperature
4. temperaturecooling
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with water and saturated brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated under reduced pressure
9. additionA mixture of the resulting residue and acetic anhydride (7 ml)
10. stirringwas stirred
11. temperatureunder reflux at 140° C. for 1 hour
12. additionAqueous sodium hydroxide solution was added to the reaction mixture
13. temperaturecooled to room temperature
14. extractionextracted with ethyl acetate
15. washThe organic layer was washed with water and saturated brine
16. dry with materialdried over sodium sulfate
17. concentrationconcentrated under reduced pressure