Реакция #74643

Уравнение реакции

3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

5-chloro-4-fluoro-2-iodophenol

potassium carbonate

→

desired product

4-(5-chloro-4-fluoro-2-iodophenoxy)-3-cyano-N-(2,4-dimethoxybenzyl)-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Растворители

dimethylsulfoxide

Условия реакции

Обработка

1. 1
   ДругоеThe flask was purged with nitrogen (3×)
2. 2
   workup.ADDITIONThe reaction was poured into a 1M aqueous solution of sodium hydroxide
3. 3
   Экстракцияextracted with dichloromethane (3×)
4. 4
   СушкаThe combined organic phase was then dried over anhydrous magnesium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Другоеthe solvent removed in vacuo

Методика

To a solution of 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 68, 335 mg, 0.77 mmol) in dimethylsulfoxide (10 ml), was added 5-chloro-4-fluoro-2-iodophenol (Preparation 734, 200 mg, 0.73 mmol) and potassium carbonate (229 mg, 1.47 mmol). The flask was purged with nitrogen (3×). The resulting suspension was allowed to stir at room temperature for 18 hours. The reaction was poured into a 1M aqueous solution of sodium hydroxide, and extracted with dichloromethane (3×). The combined organic phase was then dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo to leave the desired product as an off white solid (504 mg, 100%).

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