반응 #1847486

반응 방정식

5-bromo-1,3-dihydro-3,3-diethyl-[2H]-indol-2-one

3-chlorophenylboronic acid

potassium carbonate

→

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

수율 27.0%

용매

water

dimethoxyethane

ethanol

water

반응 조건

후처리

1. 1
   온도to reflux for 6 hours
2. 2
   추출extracted with EtOAc (2×)
3. 3
   세척The combined organic extracts were washed with water
4. 4
   건조brine, dried (MgSO4)
5. 5
   기타evaporated
6. 6
   기타The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3)

실험 절차

A solution of 5-bromo-1,3-dihydro-3,3-diethyl-[2H]-indol-2-one (2.7 g, 10 mmol), 3-chlorophenylboronic acid (1.6 g, 10 mmol), potassium carbonate (4 g, 30 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) in dimethoxyethane (100 ml), ethanol (25 ml), and water (25 ml) was heated to reflux for 6 hours. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc (2×). The combined organic extracts were washed with water, then brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3) to afford 5-(3-chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-one compound (0.8 g, 27%), m.p. 195-197° C.; 1H-NMR (DMSO-d6) δ 7.70 (t, 1H, J=2 Hz), 7.62-7.60 (m, 1H), 7.58 (d, 1H, J=1.7 Hz), 7.52 (dd, 1H, J=8.1, 2 Hz), 7.43 (t, 1H, J=7.9 Hz), 7.36-7.33 (m, 1H), 6.90 (d, 1H, J=8.1 Hz), 1.87-1.70 (m, 4H) and 0.52 (t, 6H, J=7.4 Hz); MS (+APCI) m/z 300/302 (M−H).

출처