Réaction #7086

Équation de réaction

3-chlorophenylboronic acid

sodium carbonate

5-bromo-3-methoxy-3-methyl-1,3-dihydro-indol-2-one

→

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

Rendement 29.0%

Solvants

water

dimethoxyethane

water

Conditions de réaction

Traitement

1. 1
   Températurethe reaction was heated
2. 2
   Températureunder reflux
3. 3
   TempératureAfter 2 h the mixture was cooled
4. 4
   Extractionextracted with EtOAc (×2)
5. 5
   Lavagethe combined organic extracts were washed with sodium hydroxide solution (1N, ×2) water, brine
6. 6
   Séchagedried (MgSO4)
7. 7
   Autreevaporated
8. 8
   AutreThe residue was then purified by column chromatography (SiO2, EtOAc: hexane, 5:1)

Mode opératoire

A solution of 5-bromo-3-methoxy-3-methyl-1,3-dihydro-indol-2-one (0.52 g, 2.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) was dissolved in dimethoxyethane (22 cm3). After 15 min., 3-chlorophenylboronic acid (0.63 g, 4.1 mmol) and sodium carbonate (1.0 g) in water (10 cm3) was added and the reaction was heated under reflux. After 2 h the mixture was cooled, poured into water and extracted with EtOAc (×2), the combined organic extracts were washed with sodium hydroxide solution (1N, ×2) water, brine, dried (MgSO4) and evaporated. The residue was then purified by column chromatography (SiO2, EtOAc: hexane, 5:1) to afford 5-(3-chloro-phenyl)-3-methoxy-3-methyl-1,3-dihydro-indol-2-one (0.17 g, 0.58 mmol, 29%): 1H NMR (CDCl3) δ 1.65 (s, 3H), 2.91 (s, 1H), 3.24 (s, 3H), 6.92 (d, 1H, J=8.1 Hz), 7.26–7.38 (m, 2H), 7.43–7.46 (m, 1H), 7.52–7.55 (m, 1H), 7.62 (d, 1H, J=1.8 Hz); MS ((+) APCI) m/z 288 (M+H)+.

Source