Reaktion #1704820

Reaktionsgleichung

5-[3-(4-bromo-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one

5-[3-(4-Bromo-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one

4-carboxyphenylboronic acid

water

sodium carbonate

→

title compound

4′-[3-(1-Methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Filtrationthe mixture was filtered
3. 3
   WaschenThe filter cake was washed with ethyl acetate and with a saturated KHSO4 solution
4. 4
   ExtraktionThe combined filtrate was extracted with ethyl acetate
5. 5
   TrocknenThe organic phase was dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated to dryness
8. 8
   SonstigeThe product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 9:1)

Vorschrift

To a stirred suspension of 5-[3-(4-bromo-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one (50 mg, example 162, step 3) and 4-carboxyphenylboronic acid (32 mg) in 1,4-dioxane (0.4 ml) under argon were added dichloro(1,1′-bis(diphenylphosphino)ferrocene)-palladium(II) dichloromethane adduct (4.5 mg), water (0.3 ml) and 2 M aqueous sodium carbonate solution (0.18 ml). The mixture was stirred at 80° C. for 2 h. After cooling to room temperature, the mixture was filtered. The filter cake was washed with ethyl acetate and with a saturated KHSO4 solution. The combined filtrate was extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 9:1) to give the title compound (75 mg, not totally pure) as a colorless solid, MS (ESI−): m/z=450.2 [M−H]−.

Quelle