تفاعل #5777

معادلة التفاعل

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

المردود 49.4%

المذيبات

toluene

sodium carbonate

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was degassed
2. 2
   درجة الحرارةheated
3. 3
   درجة الحرارةunder reflux for 12 hours
4. 4
   workup.ADDITIONdichloromethane (30 ml) and water (10 ml) were added
5. 5
   أخرىThe organic layer was separated
6. 6
   تجفيفdried (MgSO4)
7. 7
   أخرىthe solvent removed by evaporation
8. 8
   أخرىThe residue was purified by flash chromatography
9. 9
   غسيلeluting with ethyl acetate/hexane (3:1 v/v)
10. 10
    أخرىthe product triturated with ether/hexane

الإجراء التجريبي

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)+.

المصدر