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Toluene → 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine

HRID 1750059
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750059
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:10]=[C:5]2[N:4]=[CH:3]1.Br[C:19]1[CH:24]=[CH:23][C:22]([S:25][C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=1[S:30][CH2:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>[CH2:31]([S:30][C:20]1[CH:21]=[C:22]([S:25][C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:24][C:19]=1[C:3]1[N:2]([CH3:1])[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:10]=[C:5]2[N:4]=1)[CH3:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 1180352773-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridineHCID 1180355631-Bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene

Produkt 1

HCID 1180356092-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridineAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11776TriphenylphosphineKatalysatorHCID 165397Cupric acetate monohydrateKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 0.12 g of 3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine, 0.15 g of 1-bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene, 0.01 g of palladium(II) acetate, 0.01 g of triphenylphosphine, 0.02 g of copper(II) acetate monohydrate, 0.13 g of potassium carbonate and 3 ml of toluene was stirred under heating and refluxing for 2 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and then dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.19 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound 8).

Aufarbeitung

  1. temperatureunder heating
  2. temperaturerefluxing for 2 hours
  3. filtrationthe mixture was filtered
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-21d1dffe809c4bd296363b006f79ba2f
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156838B2

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