反应详情

To a solution of 1-[2-hydroxy-4-(2-methoxy-5-thiophen-3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (32 mg, 0.06 mmol) in methylene chloride (1 mL) at 0° C. under an argon atmosphere was added BBr3 (0.06 mL, 0.6 mmol). The mixture was warmed to room temperature, stirred 3 hours, cooled to 0° C., stirred 2 days, and quenched with methanol (5 mL). The volatiles were removed in vacuo and the residue diluted with ethyl acetate (10 mL), washed with saturated aqueous sodium bicarbonate (5 mL), and brine (5 mL), and dried over magnesium sulfate. The volatiles were removed in vacuo and the residue purified by reverse phase HPLC to afford 1-[2-hydroxy-4-(2-hydroxy-5-thiophen3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (20 mg, 68%).

1. temperaturecooled to 0° C.
2. stirringstirred 2 days
3. customquenched with methanol (5 mL)
4. customThe volatiles were removed in vacuo
5. additionthe residue diluted with ethyl acetate (10 mL)
6. washwashed with saturated aqueous sodium bicarbonate (5 mL), and brine (5 mL)
7. dry with materialdried over magnesium sulfate
8. customThe volatiles were removed in vacuo
9. customthe residue purified by reverse phase HPLC