Реакция #5777

Уравнение реакции

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

Выход 49.4%

Растворители

toluene

sodium carbonate

Условия реакции

Обработка

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

Методика

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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