反应详情

温度

90 °C

To a degassed solution of 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one (0.216 g, 0.537 mmol), 4-(hydroxymethyl)phenylboronic acid (0.122 g, 0.805 mmol) and potassium carbonate (0.223 g, 1.611 mmol) in dioxane (3.00 mL)/water (1.20 mL) was added tetrakis(triphenylphosphine)palladium (0.016 g, 0.013 mmol). Upon completion of addition, the vial was purged with argon, sealed and stirred at 90° C. for 16 h. After this time, the reaction mixture was partitioned between water and EtOAc, and the organic layer was separated. The aqueous phase was extracted with EtOAc and the combined organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (0.215 g, 93% yield) as a clear colorless oil. LCMS, [M+H]+=430.2.

1. additionUpon completion of addition
2. customthe vial was purged with argon
3. customsealed
4. customAfter this time, the reaction mixture was partitioned between water and EtOAc
5. customthe organic layer was separated
6. extractionThe aqueous phase was extracted with EtOAc
7. dry with materialthe combined organic layer was dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto provide the crude material
11. customThe crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes)