反应详情

温度

100 °C

2-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (1.75 g, 5.22 mmol), (trans)-benzyl 3-fluoro-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate (1.99 g, 6.3 mmol) and cesium carbonate (3.40 g, 10.4 mmol) were added to a sealed tube containing dimethylacetamide and heated to 100° C. overnight with stirring. The dimethylacetamide was removed under vacuum concentration and heat, chloroform was added, and this organic phase was gently washed with water. The combined organic layers were dried over MgSO4, filtered and evaporated. The crude material was purified on silica gel using a 6% solution of ammonium hydroxide in methanol and dichloromethane to yield three major products which could not be separated further by column purification (starting quinoline phenol, product and unidentified by-product). MS APCI (+) m/z 557.3 (M+1) detected. This crude material was taken directly on to the deprotection step.

1. customThe dimethylacetamide was removed under vacuum concentration
2. temperatureheat
3. additionchloroform was added
4. washthis organic phase was gently washed with water
5. dry with materialThe combined organic layers were dried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customThe crude material was purified on silica gel using a 6% solution of ammonium hydroxide in methanol and dichloromethane
9. customto yield three major products which could not
10. custombe separated further by column purification (starting quinoline phenol, product and unidentified by-product)