反应详情

温度

23 °C

A solution of n-butyllithium in hexanes (1.6 M, 1.5 mL, 2.3 mmol) was added dropwise to a stirring solution of 3-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-4-chloro-2-methoxyquinoline (1 g, 2.3 mmol, Intermediate 10) in tetrahydrofuran (18 mL) at −78° C. After 3 minutes, a solution of 1,2-dimethyl-1H-imidazole-5-carbaldehyde (347 mg, 2.8 mmol) in tetrahydrofuran (5 mL) was added dropwise. After 5 minutes, the flask was placed into an ice-water bath. After 30 minutes, water (10 mL) was added and the biphasic mixture was allowed to warm to 23° C. The mixture was partitioned between half-saturated sodium chloride solution (50 mL) and ethyl acetate (100 mL). The layers were separated. The organic layer was dried with sodium sulfate and the dried solution was filtered. Silica gel (3 g) was added to the filtrate and the solvent was removed by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a column of silica gel for purification. Elution with ethyl acetate initially, grading to 7% methanol-ethyl acetate provided the title compound as an off-white solid.

1. waitAfter 5 minutes
2. customthe flask was placed into an ice-water bath
3. waitAfter 30 minutes
4. customThe mixture was partitioned between half-saturated sodium chloride solution (50 mL) and ethyl acetate (100 mL)
5. customThe layers were separated
6. dry with materialThe organic layer was dried with sodium sulfate
7. filtrationthe dried solution was filtered
8. additionSilica gel (3 g) was added to the filtrate
9. customthe solvent was removed by rotary evaporation
10. customto afford a free-flowing powder
11. customThe powder was loaded onto a column of silica gel for purification
12. washElution with ethyl acetate initially