反应详情

温度

90 °C

Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (46 mg, 0.158 mmol) was dissolved in toluene (500 μL), ethanol (96%) (237 μL) and aqueous sodium carbonate 2M (237 μL, 0.473 mmol). tert-Butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (97 mg, 0.21 mmol) was added. The mixture was degassed with argon and 1,1′-bis(diphenylphosphino)-ferrocene palladium(II) dichloride (11.5 mg, 0.016 mmol) was added. The mixture was heated at 90° C. for 4 h. After cooling, the mixture was diluted with CH2Cl2 (3 mL) and water (3 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×2 mL). The organic layer was concentrated in vacuo. The crude product was purified with flash silica column chromatography (heptane:ethyl acetate) (1:1 to 1:2) to afford the title compound as a yellow solid (24 mg, 32%). ESI-MS m/z: 481 (M+H)+.

1. additionwas added
2. temperatureAfter cooling
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with CH2Cl2 (3×2 mL)
5. concentrationThe organic layer was concentrated in vacuo
6. customThe crude product was purified with flash silica column chromatography (heptane:ethyl acetate) (1:1 to 1:2)