Réaction #7076

Équation de réaction

5-bromo-2-indolinone

3-nitrophenyl boronic acid

potassium carbonate

→

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

Rendement 65.0%

Solvants

ethylene glycol dimethyl ether

water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source