Reaction #5777

Reaction equation

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

Yield 49.4%

Solvents

toluene

sodium carbonate

Conditions

Workup

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

Procedure

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)+.

Source