反应详情

温度

165 °C

4-(N-(furan-2-ylmethyl)sulfamoyl)benzoic acid (Example 5-2b) (140 mg, 0.5 mmol) and Cesium Carbonate (325 mg, 1 mmol) were placed in a microwave vial and dissolved in 2 mL DMF. (Bromomethyl)benzene (170 mg, 1 mmol) was added into the reaction mixture. The reaction was placed in a microwave reactor and heated at 165° C. for 5 minutes. The reaction mixture was dissolved in Ethyl Acetate and washed with water. The organic layer was dried over sodium sulfate and evaporated under vacuum. The crude product was dissolved in 4/1 solution of 6N NaOH (aq)/tetrahydrofuran (3 mL) and stirred at ambient temperature for 6 hours. The solution was acidified with 3N HCl (aq) to a pH of ˜3 and the product was extracted with ethyl acetate (3×, 75 mL). The combined organic extracts were dried over sodium sulfate and concentrated under vacuum. The residue was taken up in methanol (3 mL) and purified by reverse phased HPLC (5-95% acetonitrile in H2O gradient: 25 minutes). Yield 35%. MS M+H calculated 372.4, found 372.0.

1. customThe reaction was placed in a microwave reactor
2. washwashed with water
3. dry with materialThe organic layer was dried over sodium sulfate
4. customevaporated under vacuum
5. dissolutionThe crude product was dissolved in 4/1 solution of 6N NaOH (aq)/tetrahydrofuran (3 mL)
6. extractionthe product was extracted with ethyl acetate (3×, 75 mL)
7. dry with materialThe combined organic extracts were dried over sodium sulfate
8. concentrationconcentrated under vacuum
9. custompurified by reverse
10. customHPLC (5-95% acetonitrile in H2O gradient: 25 minutes)