Reaktion #7104

Reaktionsgleichung

ammonium chloride

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

3-chloro-4-fluorobenzene boronic acid

potassium carbonate

→

title compound

Ausbeute 30.0%

5-(3-Chloro-4-fluoro-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-one

Ausbeute 30.0%

Lösungsmittel

water

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 16 h
2. 2
   Extraktionextracted with EtOAc (×3)
3. 3
   TrocknenThe combined organic extracts were dried (MgSO4)
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue was purified by column chromatography (SiO2, ethyl acetate: hexane 1:3)

Vorschrift

A solution of 5-bromo-3,3-dimethyl-1,3-dihydro-indol-2-one (0.35 g, 1.46 mmol) and tetrakis(triphenylphosphine) palladium (0.13 g, 0.11 mmol) in dimethoxyethane (10 cm3) was stirred under N2 for 20 min. To this mixture was then added 3-chloro-4-fluorobenzene boronic acid (0.26 g, 1.49 mmol) and potassium carbonate (0.62 g, 4.5 mmol) in water (5 cm3). The solution was brought to reflux for 16 h then cooled to RT, poured into saturated ammonium chloride and extracted with EtOAc (×3). The combined organic extracts were dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, ethyl acetate: hexane 1:3) to afford the title compound (0.124 g, 0.43 mmol, 30%) as a white solid: m.p. 206.5–207.8° C., 1H NMR (DMSO-d6) δ 1.3 (s, 6H), 6.93 (d, J=8.1 Hz, 1H), 7.45 (dd, J=8.9, 8.9 Hz, 1H), 7.5 (dd, J=8.1, 1.8 Hz, 1H), 7.6 (ddd, J=8.9, 7.1, 2.2 Hz, 1H), 7.7 (d, J=1.8 Hz, 1H), 7.8 (dd, J=7.1, 2.2 Hz, 1H), 10.5 (s, 1H (EI) m/z 289/291 (M)+.

Quelle