反应详情

A solution of EtMgBr (3.0 M in diethylether, 8.5 mL, 25.69 mmol) was added dropwise, over a 25 minute period to a solution of 5-bromo-1-methyl-1H-imidazole (4.1 g, 25.69 mmol) in dry DCM (25 mL). The mixture was stirred at room temperature for 15 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (4.8 g, 21.41 mmol. Intermediate 13: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and the mixture stirred at room temperature for 48 hours. Water was added to the suspension followed by 6 M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and the layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and the precipitates filtered to provide the title compound as a tan solid.

1. temperaturecooled in an ice-brine bath
2. additionwas added dropwise
3. customA dark brown solid mass formed
4. customThe ice bath was removed
5. stirringthe mixture stirred at room temperature for 48 hours
6. additionWater was added to the suspension
7. additionMore DCM was added
8. customthe layers were separated
9. dry with materialThe organic layer was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. additionEt2O was added
13. customthe slurry sonicated
14. filtrationthe precipitates filtered