반응 #9420

반응 방정식

ammonium chloride

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one

3-methoxyphenylboronic acid

potassium carbonate

→

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

수율 31.0%

용매

EtOAc

water

dimethoxyethane

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도to reflux for 5 hours
3. 3
   여과the mixture was filtered
4. 4
   추출The aqueous layer was extracted with EtOAc (×2)
5. 5
   건조the combined organic layers were dried (MgSO4)
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3)

실험 절차

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (0.33 g, 1.38 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.094 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (12 cm3). After 15 minutes, 3-methoxyphenylboronic acid (0.42 g, 2.76 mmol) was added, followed by potassium carbonate (1.15 g, 8.34 mmol) in water (5 cm3). The reaction was heated to reflux for 5 hours, and then cooled to room temperature. Saturated aqueous ammonium chloride and EtOAc were added and the mixture was filtered. The aqueous layer was extracted with EtOAc (×2), and the combined organic layers were dried (MgSO4), filtered, and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3) to afford 5-(3-methoxy-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-one (0.11 g, 31%), mp=157–158° C.; 1H NMR (DMSO-d6) δ 3.34 (s, 6 H), 3.82 (s, 3 H), 6.87–6.93 (m, 2 H), 7.20–7.15 (m, 2 H), 7.37–7.32 (m, 1 H), 7.49–7.46 (m, 1 H), 7.63 (d, 1 H, J=1.14 Hz), 10.4 (s, 1 H); MS (EI) m/z 266 (M−H)−; CHN calculated for C17H17NO2: C, 76.38; H, 6.41; N, 5.24. Found: C, 76.02; H, 6.49; N, 5.02.

출처