Reacción #7076

Ecuación de reacción

5-bromo-2-indolinone

3-nitrophenyl boronic acid

potassium carbonate

→

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

Rendimiento 65.0%

Disolventes

ethylene glycol dimethyl ether

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was heated
2. 2
   Temperaturato reflux overnight
3. 3
   Filtraciónfiltered
4. 4
   workup.ADDITIONSaturated ammonium chloride was added
5. 5
   ExtracciónThe water layer was extracted with ethyl acetate (3×20 mL)
6. 6
   SecadoThe combined organic layer was dried with MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Otrosolvent removed in vacuo
9. 9
   OtroThe product was purified by flash silica gel chromatography (3:2 hexane; ethyl acetate)

Procedimiento

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.

Fuente