反应详情

To a solution of 5-bromo-1-methyl-1H-imidazole (3.22 g, 19.98 mmol) in DCM (15 mL) was added ethyl magnesium bromide (6.66 mL, 19.98 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting orange-red solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0° C. and N-methoxy-N-methyl-4-nitrobenzamide (3.5 g, 16.65 mmol, Intermediate 7: step a) dissolved in DCM (10 mL) was added dropwise. The ice bath was removed and the solid suspension stirred at room temperature for 48 hours. Water was added followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitate was collected by filtration and dried to provide the title compound as a tan solid.

1. temperaturecooled in an ice bath to 0° C.
2. additionwas added dropwise
3. customThe ice bath was removed
4. stirringthe solid suspension stirred at room temperature for 48 hours
5. additionWater was added
6. extractionThe aqueous mixture was extracted with DCM
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. additionEt2O was added
11. customthe mixture sonicated
12. filtrationThe precipitate was collected by filtration
13. customdried