Potassium Carbonate → HCID 178493168, Verbindung

HRID 1179411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1179411
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)(=[O:7])=[O:6].C([O-])(=O)C.[K+].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([CH2:28][CH2:29][C:30]2[NH:39][C:33]3=[N:34][CH:35]=[C:36](I)[CH:37]=[C:32]3[N:31]=2)[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:36]2[CH:37]=[C:32]3[N:31]=[C:30]([CH2:29][CH2:28][C:24]4[CH:23]=[C:22]([O:21][CH3:20])[CH:27]=[CH:26][N:25]=4)[NH:39][C:33]3=[N:34][CH:35]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Komponenten

11

Edukt 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 4585694-bromo-N-(2-hydroxyethyl)benzenesulfonamideHCID 517044Potassium AcetateHCID 178493175HCID 178493175, Verbindung2×

Produkt 1

HCID 178493168HCID 178493168, VerbindungAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 0.42 g of N-(2-hydroxyethyl)-4-bromobenzenesulfonamide, 0.42 g of bis-(pinacolato)-diboron, 0.025 g of 1,1′-bis-(diphenylphosphino)-ferrocene, 0.033 g of [1,1′-bis(diphenylphosphino)-ferrocene]palladium-dichloride (complex with CH2Cl2), 0.442 g of potassium acetate in 6 ml of degassed dioxane are heated to 90° C. in a sealed tube under N2 for 7 hours. To the resulting mixture 5 ml of degassed dioxane, 0.371 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (starting material A1), 0.113 g of tetrakis(triphenylphosphine)-palladium(0) and a solution of 0.27 g of potassium carbonate and 0.083 g of lithium chloride in 5 ml of degassed water are added under N2. The tube is sealed again, the mixture is heated to 115° under N2 for 17 hours and, after cooling, addition of water and adjusting the pH to 7, it is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, concentrated and the residue is chromatographed on a silica gel column (dichloromethane/methanol 15-8:1+1% NH4OH). Concentration of the chromatographically pure fractions and crystallisation from ethanol gives 0.20 g of the title compound as a solid of m.p. 218-220° C. The mass spectrum shows the molecular peak MH+ at 454.1 Da.

Aufarbeitung

  1. customThe tube is sealed again
  2. temperaturethe mixture is heated to 115° under N2 for 17 hours
  3. temperatureafter cooling
  4. extractionis extracted three times with dichloromethane
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue is chromatographed on a silica gel column (dichloromethane/methanol 15-8:1+1% NH4OH)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-99ae46fbc45e4a96a98e64f9e647311c
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279488B2

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