反应详情

温度

65 °C

To a solution of 3-cyano-N-(2,4-dimethoxybenzyl)-4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 29, 45.5 mg, 0.086 mmol) in tetrahydrofuran (1 mL) was added a 2 M aqueous solution of potassium carbonate (116 μL, 3.03 mmol) and 2-methoxy-4-(trifluoromethyl)benzyl bromide (21 mg, 0.08 mmol). The solution was sparged with nitrogen before the addition of tetrakis(triphenylphosphine)palladium (0) (9.2 mg, 0.0008 mmol). The reaction mixture was heated at 65° C. for 6 hours. The reaction mixture was cooled to ambient temperature and partitioned between 1N aqueous citric acid solution (2 mL) and ethyl acetate (10 mL). The organic layer was washed with a saturated aqueous solution of sodium chloride (2 mL), dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give a yellow oil. The material was purified by silica gel column chromatography (ISCO™ companion, 12 g column, 0-50% ethyl acetate in heptane gradient elution). Fractions containing product were combined and concentrated in vacuo to obtain the title compound as a yellow oil, which was used without further purification.

1. temperatureThe reaction mixture was cooled to ambient temperature
2. custompartitioned between 1N aqueous citric acid solution (2 mL) and ethyl acetate (10 mL)
3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride (2 mL)
4. dry with materialdried over anhydrous magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a yellow oil
8. customThe material was purified by silica gel column chromatography (ISCO™ companion, 12 g column, 0-50% ethyl acetate in heptane gradient elution)
9. additionFractions containing product
10. concentrationconcentrated in vacuo