反应详情

In a round bottom flask, 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (27, 0.400 g, 1.64 mmol) is combined with 10 mL of methanol and potassium hydroxide (0.256 g, 4.56 mmol). Propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (28, 0.400 g, 1.52 mmol) is added and the reaction is stirred at room temperature for 3 hours, with additional potassium hydroxide added up to 7 equivalents. The reaction is concentrated under vacuum, the solid added to water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with a gradient of 10-100% ethyl acetate (with 2.5% acetic acid) in hexanes. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=508.37.

1. additionadded up to 7 equivalents
2. concentrationThe reaction is concentrated under vacuum
3. additionthe solid added to water
4. extractionextracted with ethyl acetate
5. dry with materialThe organic layer is dried over sodium sulfate
6. filtrationfiltered
7. concentrationthe filtrate concentrated under vacuum
8. customThe resulting material is purified by silica gel column chromatography
9. washeluting with a gradient of 10-100% ethyl acetate (with 2.5% acetic acid) in hexanes
10. concentrationconcentrated under vacuum