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

HRID 5681

Reaktionsgleichung

Reaktionsgleichung von HRID 5681
[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1)[CH3:2].Br[C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[C:27]#[N:28]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C:11]2[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[N:4]=[C:3]([CH2:1][CH3:2])[CH:12]=2)=[CH:16][CH:17]=1)#[N:28]

Komponenten

6

Edukt 2

HCID 162722-BromobenzonitrileHCID 151714224-[(2-Ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acid

Produkt 1

HCID 197964084-[(2'-Cyanobiphenyl-4-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinolineAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  1. customThe mixture was degassed
  2. temperatureheated
  3. temperatureunder reflux for 12 hours
  4. additiondichloromethane (30 ml) and water (10 ml) were added
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate/hexane (3:1 v/v)
  10. customthe product triturated with ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-f2e47c7899134a9295da63016e60ddb0
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245035

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