Reaktion #7076

Reaktionsgleichung

5-bromo-2-indolinone

3-nitrophenyl boronic acid

potassium carbonate

→

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

Ausbeute 65.0%

Lösungsmittel

ethylene glycol dimethyl ether

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturto reflux overnight
3. 3
   Filtrationfiltered
4. 4
   workup.ADDITIONSaturated ammonium chloride was added
5. 5
   ExtraktionThe water layer was extracted with ethyl acetate (3×20 mL)
6. 6
   TrocknenThe combined organic layer was dried with MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigesolvent removed in vacuo
9. 9
   SonstigeThe product was purified by flash silica gel chromatography (3:2 hexane; ethyl acetate)

Vorschrift

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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