反应详情

温度

90 °C

To a degassed mixture of 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutan-1-one (0.208 g, 0.698 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (0.532 g, 2.094 mmol), and potassium acetate (0.411 g, 4.19 mmol) in DMF (10 mL) was added PdCl2(dppf)-CH2Cl2 (0.057 g, 0.070 mmol). The vial was purged with argon, sealed, and stirred at 90° C. for 2 d. tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate (0.5 g, 1.396 mmol), PdCl2(dppf)-CH2Cl2 (0.057 g, 0.070 mmol), and 2 M Na2CO3 (2 mL, 1.396 mmol) were added. The reaction mixture was purged with argon and stirred at 95° C. overnight. At the conclusion of this period, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic extract was dried, concentrated, and purified by flash chromatography (0-100% ethyl acetate:hexanes then 10% CH3OH:ethyl acetate) to afford the title compound (0.24 g, 69% yield) as a dark brown oil. LCMS, [M+H]+=497.4.

1. customThe vial was purged with argon
2. customsealed
3. customThe reaction mixture was purged with argon
4. stirringstirred at 95° C. overnight
5. customAt the conclusion of this period, the reaction mixture was quenched with water
6. extractionextracted with ethyl acetate
7. extractionThe organic extract
8. customwas dried
9. concentrationconcentrated
10. custompurified by flash chromatography (0-100% ethyl acetate