Reaktion #59157

Reaktionsgleichung

3-(4-bromo-benzoyl)-cyclohexanecarboxylic acid methyl ester

4-aminophenyl boronic acid

→

3-(4′-amino-biphenyl-4-carbonyl)-cyclohexanecarboxylic acid methyl ester

Lösungsmittel

toluene

dioxane

Na2CO3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was degassed
2. 2
   Sonstigeby bubbling with a flow of argon for 45 minutes
3. 3
   TemperaturThe reaction mixture was cooled to rt
4. 4
   Filtrationfiltered through a pad of Celite®
5. 5
   Waschenrinsing with ethyl acetate
6. 6
   SonstigeThe organic layer was separated
7. 7
   Waschenwashed with water and brine
8. 8
   Trocknendried (Na2SO4)
9. 9
   SonstigeThe solvent was removed by rotary evaporation
10. 10
    Sonstigethe solid residue was purified

Vorschrift

To a solution of 3-(4-bromo-benzoyl)-cyclohexanecarboxylic acid methyl ester (500 mg, 1.54 mmol) and 4-aminophenyl boronic acid (252 mg, 1.85 mmol) in toluene (40 mL) and dioxane (10 mL), 2 N aqueous Na2CO3 (10 mL) was added, and the mixture was degassed by bubbling with a flow of argon for 45 minutes. (1,1-Bis(diphenylphosphino)ferrocene)-dichloropalladium (63 mg, 0.08 mmol) was added to the mixture, which was then heated at 80° C. overnight. The reaction mixture was cooled to rt, and then filtered through a pad of Celite®, rinsing with ethyl acetate. The organic layer was separated, washed with water and brine, and dried (Na2SO4). The solvent was removed by rotary evaporation, and the solid residue was purified by using a Biotage QuadUV flash chromatography system (eluant: 3:1 hexane/EtOAc). The product 3-(4′-amino-biphenyl-4-carbonyl)-cyclohexanecarboxylic acid methyl ester was obtained as a brown solid (200 mg, yield 38.5%). 1H NMR (300 MHz, DMSO) δ 7.90 (d, 2H), 7.60 (d, 2H), 7.45 (d, 2 H), 6.80 (d, 2H), 3.70 (s, 3H), 3.25 (m, 1H), 2.50 (m, 1H), 2.20-1.90 (m, 4 H), 1.70-1.50 (m, 4H); LC-MS ret. time 3.80 min (method 2), m/z 338.17 (MH+).

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