Reaktion #9425

Reaktionsgleichung

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

Ausbeute 27.0%

Lösungsmittel

water

dimethoxyethane

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 6 hours
2. 2
   Extraktionextracted with EtOAc (2×)
3. 3
   WaschenThe combined organic extracts were washed with water
4. 4
   Trocknenbrine, dried (MgSO4)
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3)

Vorschrift

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).

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