反应详情

5-Bromo-1H-pyrazolo[3,4-b]pyridin-3-ol (8.68 g, 40.56 mmol) and 1-(chloromethyl)-4-methoxybenzene (16.50 mL, 121.7 mmol) were dissolved in DMSO (250 mL). Powdered NaOH (2.433 g, 60.84 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between EtOAc and water and separated. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with water (3×), saturated aqueous NaHCO3 (3×), brine, and dried over Na2SO4 and concentrated giving an oily solid. This solid was triturated with EtOAc and dried to provide 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-ol (7.0 g, 51.7%) as a solid.

1. customThe reaction mixture was partitioned between EtOAc and water
2. customseparated
3. extractionThe aqueous layer was extracted with EtOAc (3×)
4. washThe combined organic layers were washed with water (3×), saturated aqueous NaHCO3 (3×), brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customgiving an oily solid
8. customThis solid was triturated with EtOAc
9. customdried