반응 #7076

반응 방정식

5-bromo-2-indolinone

3-nitrophenyl boronic acid

potassium carbonate

→

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

수율 65.0%

용매

ethylene glycol dimethyl ether

water

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도to reflux overnight
3. 3
   여과filtered
4. 4
   workup.ADDITIONSaturated ammonium chloride was added
5. 5
   추출The water layer was extracted with ethyl acetate (3×20 mL)
6. 6
   건조The combined organic layer was dried with MgSO4
7. 7
   여과filtered
8. 8
   기타solvent removed in vacuo
9. 9
   기타The product was purified by flash silica gel chromatography (3:2 hexane; ethyl acetate)

실험 절차

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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