Toluene → HCID 21186228, Verbindung

HRID 361421

Reaktionsgleichung

Reaktionsgleichung von HRID 361421
Cl[C:2]1[C:7]([S:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:21]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[CH:22]([CH3:24])[CH3:23].[F-].[K+].C1(C)C=CC=CC=1>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.O>[CH2:21]([C:25]1[CH:30]=[CH:29][C:28]([C:2]2[C:7]([S:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:27][CH:26]=1)[CH:22]([CH3:24])[CH3:23]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 522689Potassium FluorideHCID 2773472(4-Isobutylphenyl)boronic acidHCID 21186255HCID 21186255, Verbindung

Produkt 1

HCID 21186228HCID 21186228, VerbindungAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.076 g) was added to a deoxygenated mixture of 4-nitrophenyl 2-chloropyridine-3-sulphonate (0.69 g), 4-isobutylphenylboronic acid (0.47 g), potassium fluoride (0.38 g), toluene (15 ml) and water (2.5 ml) and the mixture was stirred and heated under reflux for 24 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2×80 ml). The organic extracts were washed with saturated sodium chloride solution and then combined and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with dichloromethane/hexane (1:1-1:0 v/v) then dichloromethane/hexane/ethyl acetate (10:9:1 v/v) through a silica gel Mega Bond Elut column followed by recrystallisation from ethyl acetate/hexane to give 4-nitrophenyl 2-(4-isobutylphenyl)pyridine-3-sulphonate (0.50 g), m.p. 123°-124° C.; 1H NMR (d6 -DMSO): 0.9 (d, 6 H), 1.9 (m, 1 H), 2.55 (d, 2 H), 7.2-7.3 (m, 4 H), 7.5 (d, 2 H), 7.7 (dd, 1 H), 8.2 (d, 2 H), 8.4 (dd, 1 H), 9.0 (dd, 1 H); mass spectrum (+ve FAB, NBA/DMSO): 413 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. extractionthe mixture was extracted with ethyl acetate (2×80 ml)
  4. washThe organic extracts were washed with saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by gradient elution with dichloromethane/hexane (1:1-1:0 v/v)
  8. customdichloromethane/hexane/ethyl acetate (10:9:1 v/v) through a silica gel Mega Bond Elut column followed by recrystallisation from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c7b6641b89b742aaa64ebc1c02e842f3
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866568

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