Water → 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline

HRID 5675

Reaktionsgleichung

Reaktionsgleichung von HRID 5675
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:18]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[N:17]=[N:16][N:15]=1.O.Cl.[CH2:30]([C:32]1[CH:41]=[C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=2)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1)[CH3:31]>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.C1(C)C=CC=CC=1.CO>[CH2:30]([C:32]1[CH:41]=[C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:14]3[N:18]([C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=4)[N:17]=[N:16][N:15]=3)=[CH:46][CH:45]=2)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1)[CH3:31]

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 199357905-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole2×HCID 677828274-[(2-Ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride

Produkt 1

HCID 199357842-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinolineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of potassium carbonate (5.8 g), 5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole (5.81 g) (Compound B), water (43 ml), toluene (43 ml), and methanol (43 ml) was heated to 60° C. to give a clear solution. 4-[(2-Ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride (4.3 g) and tetrakis(triphenylphosphine)palladium (0.032 g) were added and the reaction mixture heated at reflux for 4 hours. The mixture was allowed to cool and further toluene (50 ml) added. The organic phase was separated and the aqueous phase extracted with toluene (2×50 ml). The combined organic phases were evaporated and the resultant solid recrystallised from toluene to give 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline as a solid (4.3 g); NMR (CDCl3): 1.42(3H,t), 3.0(2H,q), 5.23(2H,s), 6.67(2H,d), 6.75(1H,s), 6.85(2H,d), 7.25 (2H,d), 7.43(1H,d), 7.55(1H,t), 7.70(3H,m), 7.90(3H,d), 8.05(1H,d), 8.20(1H,d).

Aufarbeitung

  1. customto give a clear solution
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 4 hours
  4. temperatureto cool
  5. customThe organic phase was separated
  6. extractionthe aqueous phase extracted with toluene (2×50 ml)
  7. customThe combined organic phases were evaporated
  8. customthe resultant solid recrystallised from toluene

Quellen und Nachweise

ORD-Eintrag
ord-46152c9e14d74da38cf75a60bb4c02b6
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245035

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