反应详情

To 6-fluoro-8-isopropoxy-2-methylquinoline (1.1 g, 5.02 mmol) in dioxane/water (3.5 ml/0.3 mL) at ambient temperature was added selenium dioxide (0.668 g, 6.02 mmol) and the reaction was heated to reflux for 2-3 hours. After cooling, the reaction was filtered and the solids were washed with DCM. The filtrate was dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 6-fluoro-8-isopropoxyquinoline-2-carbaldehyde (410 mg, 35.0% yield) as a tan solid.

1. temperaturethe reaction was heated
2. temperatureto reflux for 2-3 hours
3. temperatureAfter cooling
4. filtrationthe reaction was filtered
5. washthe solids were washed with DCM
6. dry with materialThe filtrate was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude material was purified by reverse phase chromatography (SP4, 25M
10. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)