反应详情

To a stirred suspension of 3-(1H-imidazol-4-yl)pyridine dihydrochloride (1.745 g, 8 mmol) in a mixture of tetrahydrofuran (29 mL) and DMF (2.90 mL) was added potassium 2-methylpropan-2-olate (1.795 g, 16.0 mmol) and the mixture was refluxed for 30 minutes. The resulting brown suspension was cooled to room temperature and treated with pyridine (0.979 mL, 12 mmol) and N,N-dimethylpyridin-4-amine (0.098 g, 0.8 mmol), followed by the addition of cyclohexyl(methyl)carbamic chloride (1.476 g, 8.4 mmol). The reaction was heated to 90° C. overnight, whereupon the mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried (MgSO4) and filtered. After evaporation, the crude product was chromatographed over silica gel using a dichloromethane/methanol (9:1) mixture. Homogenous fractions were pooled and evaporated to leave a white powder, (160 mg, 7%).

1. temperaturethe mixture was refluxed for 30 minutes
2. temperatureThe reaction was heated to 90° C. overnight, whereupon the mixture
3. extractionextracted with ethyl acetate
4. dry with materialThe organic phase was dried (MgSO4)
5. filtrationfiltered
6. customAfter evaporation
7. customthe crude product was chromatographed over silica gel using a dichloromethane/methanol (9:1) mixture
8. customevaporated
9. customto leave a white powder, (160 mg, 7%)