反应详情

温度

0 °C

To a stirred mixture of [1-ethyl-3-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate (150 mg) and EtOH (3 mL) was added 1N NaOH (2 ml) at 0° C. The mixture was stirred at 0° C. for 30 min, treated with saturated NH4Cl solution, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in DMA (4 ml) and KOtBu (52 mg) was added at room temperature. The mixture was stirred for 2 min, and then 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (97 mg) was added. The mixture was stirred at 150° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (NH, AcOEt/MeOH=20/1) and crystallized from AcOEt/hexane to give the title compound (46 mg).

1. extractionextracted with AcOEt
2. dry with materialThe organic layer was dried over MgSO4
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in DMA (4 ml)
5. additionKOtBu (52 mg) was added at room temperature
6. stirringThe mixture was stirred for 2 min
7. addition3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (97 mg) was added
8. stirringThe mixture was stirred at 150° C. for 30 min
9. additiontreated with water
10. extractionextracted with AcOEt
11. dry with materialThe organic layer was dried over MgSO4
12. concentrationconcentrated in vacuo
13. customThe residue was purified by silica gel column chromatography (NH, AcOEt/MeOH=20/1)
14. customcrystallized from AcOEt/hexane