反应详情

温度

-70 °C

To a solution of n-BuLi (12.9 mL 1.6 M in hexane) was added dropwise a solution of 4-bromo-2-methylpyridine (3.56 g) in THF (170 mL) at −70° C. over a period of 20 min. The reaction mixture was stirred at −70° C. for 5 min, before a solution of 3-(4-bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamide (2.5 g) in THF (100 mL) was added dropwise. After the addition was complete, the mixture was stirred at −70° C. for 3 hours. A saturated solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to give the title compound as an yellow oil (1.49 g, 55%), MS (ESI+): m/z=394.0797 ([M+H]+, 1Br).

1. additionwas added dropwise
2. additionAfter the addition
3. customthe phases were separated
4. extractionthe inorganic one was extracted with EtOAc (2×)
5. washThe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1)