Реакция #7076

Уравнение реакции

5-bromo-2-indolinone

3-nitrophenyl boronic acid

potassium carbonate

→

5-(3-Nitro-phenyl)-1,3-dihydro-indol-2-one

Выход 65.0%

Растворители

ethylene glycol dimethyl ether

water

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураto reflux overnight
3. 3
   Фильтрацияfiltered
4. 4
   workup.ADDITIONSaturated ammonium chloride was added
5. 5
   ЭкстракцияThe water layer was extracted with ethyl acetate (3×20 mL)
6. 6
   СушкаThe combined organic layer was dried with MgSO4
7. 7
   Фильтрацияfiltered
8. 8
   Другоеsolvent removed in vacuo
9. 9
   ДругоеThe product was purified by flash silica gel chromatography (3:2 hexane; ethyl acetate)

Методика

5-bromo-2-indolinone (1.08 g, 5.09 mmol) and tetrakistriphenyl phosphine Pd (0) (0.273 g) were stirred under an atmosphere of nitrogen in ethylene glycol dimethyl ether (35 mL). After 15 minutes, 3-nitrophenyl boronic acid (1.70 g, 10.2 mmol) was added, followed by potassium carbonate (4.24 g, 30.7 mmol) in water (15 mL). The reaction was heated to reflux overnight, cooled to room temperature and then filtered. Saturated ammonium chloride was added. The water layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried with MgSO4, filtered, and solvent removed in vacuo. The product was purified by flash silica gel chromatography (3:2 hexane; ethyl acetate) to give 5-(3-Nitro-phenyl)-1,3-dihydro-indol-2-one (0.084 g, 65%), Mp=269° C.; 1H NMR (DMSO) δ 10.5 (s, 1H), 8.38–8.36 (m, 1H) 8.17–8.14 (m, 1H), 8.10–8.07 (m, 1H), 7.75–7.60 (m, 3H), 6.95 (d, 1H, J=8.1 Hz), 3.57 (s, 2H); IR (KBr) 3420, 3190, 1700 cm−1; MS (EI) m/z 253 (M−H)−; CHN calculated for C14H10N2O: C, 66.14; H, 3.96; N, 11.02; Found: C, 64.59; H, 4.16; N, 9.43.

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