Реакция #675444

Уравнение реакции

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

2-bromo-5-phenyl-1,3,4-thiadiazole

potassium carbonate

→

5-(5-phenyl-1,3,4-thiadiazol-2-yl)indolin-2-one

Выход 25.1%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   ЭкстракцияThe residue was extracted with EtOAc
2. 2
   Промывкаthe organic layer was washed with H2O and brine
3. 3
   Сушкаdried over Na2SO4
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   ДругоеThe residue was purified by column chromatography (n-hexane/EtOAc)

Методика

To a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (98 mg, 0.38 mmol) in dioxane (0.76 ml) was added PdCl2(dppf) CH2Cl2 (28 mg, 0.039 mmol), 2-bromo-5-phenyl-1,3,4-thiadiazole (138 mg, 0.57 mmol) and 2 M potassium carbonate (aq, 568 μL). The mixture was stirred at 90° C. for 4 hour. The residue was extracted with EtOAc, and the organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (n-hexane/EtOAc) to give 5-(5-phenyl-1,3,4-thiadiazol-2-yl)indolin-2-one (28 mg) as brown oil.

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