Reaktion #5777

Reaktionsgleichung

4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]-phenylboronic acid

2-bromobenzonitrile

→

4-[(2'-cyanobiphenyl-4-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline

Ausbeute 49.4%

Lösungsmittel

toluene

sodium carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   Temperaturheated
3. 3
   Temperaturunder reflux for 12 hours
4. 4
   workup.ADDITIONdichloromethane (30 ml) and water (10 ml) were added
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried (MgSO4)
7. 7
   Sonstigethe solvent removed by evaporation
8. 8
   SonstigeThe residue was purified by flash chromatography
9. 9
   Wascheneluting with ethyl acetate/hexane (3:1 v/v)
10. 10
    Sonstigethe product triturated with ether/hexane

Vorschrift

Tetrakis(triphenylphosphine)palladium (40 mg) was added to a suspension of 4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]-phenylboronic acid (200 mg) and 2-bromobenzonitrile (106 mg) in toluene (2 ml) ethanol (0.5 ml) and 2M aqueous sodium carbonate (0.58 ml). The mixture was degassed and placed under an atmosphere of argon, then heated under reflux for 12 hours. The resulting solution was cooled to ambient temperature, and dichloromethane (30 ml) and water (10 ml) were added. The organic layer was separated, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (3:1 v/v), and the product triturated with ether/hexane to give 4-[(2'-cyanobiphenyl-4-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline (106 mg) as a white solid, m.p. 147°-148° C.; NMR (CDCl3): 1.29(t,3H), 1.7-1.95(m,4H), 5.17(s,2H), 6.57(s,1H), 7.4-7.7 (complex m,7 H), 7.78(d,1H); mass spectrum (+ve CI) 369 (M+H)+.

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