反应详情

4-Methylphenyl 5-chloro-2,4-difluorobenzoate (Preparation 26, 0.330 g, 1.168 mmol) was added portionwise over 5 minutes to a suspension of 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 69, 0.214 g, 1.262 mmol) and potassium carbonate (0.32 g, 2.315 mmol) in DMSO (5.0 mL). The mixture was stirred at room temperature for 3 hours, then partitioned between water (20.0 mL) and tert-butyl methyl ether (20.0 mL). The organic layer was further washed with water (2×20.0 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting crude product was purified with silica gel chromatography eluting with 0 to 5% EtOAc in heptane to yield the title compound as a white solid (0.289 g, 0.668 mmol, 57%):

1. custompartitioned between water (20.0 mL) and tert-butyl methyl ether (20.0 mL)
2. washThe organic layer was further washed with water (2×20.0 mL)
3. dry with materialThe organic layer was dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe resulting crude product was purified with silica gel chromatography
7. washeluting with 0 to 5% EtOAc in heptane