反应详情

温度

65 °C

To a solution of tetrahydrofuran (10 mL) and water (2 mL) was added 3-chloro-2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 221, 32 mg, 0.11 mmol), 4-(bromomethyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide (Preparation 243, 43 mg, 0.13 mmol) and potassium carbonate (46 mg, 0.35 mmol). The flask was degassed with N2 (×5), and tetrakistriphenylphosphinepalladium (13.2 mg, 0.01 mmol) was added. The flask was degassed with N2 (×5), and heated to 65° C. for 18 hours. The reaction was allowed to cool to room temperature and washed with a saturated aqueous solution of ammonium chloride (100 mL). The reaction was extracted into ethyl acetate (3×50 mL). The combined organic layers were dried over MgSO4, filtered and the solvent removed to leave a yellow oil. The material was purified by silica gel column chromatography eluting with 1:1 heptane:ethyl acetate to afford the title compound as a yellow oil that solidified to a pale yellow solid upon standing (23 mg, 48%).

1. additionwas added
2. customThe flask was degassed with N2 (×5)
3. temperatureto cool to room temperature
4. washwashed with a saturated aqueous solution of ammonium chloride (100 mL)
5. extractionThe reaction was extracted into ethyl acetate (3×50 mL)
6. dry with materialThe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. customthe solvent removed
9. customto leave a yellow oil
10. customThe material was purified by silica gel column chromatography
11. washeluting with 1:1 heptane