Reacción #5777

Ecuación de reacción

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

Rendimiento 49.4%

Disolventes

toluene

sodium carbonate

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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)+.

Fuente