Potassium Carbonate → HCID 178493162, Verbindung

HRID 1179421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1179421
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]([CH2:33][CH2:34][C:35]2[NH:44][C:38]3=[N:39][CH:40]=[C:41](I)[CH:42]=[C:37]3[N:36]=2)[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>O1CCOCC1.O.[CH-]1C=CC=C1.[CH-]1C=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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:41]3[CH:42]=[C:37]4[N:36]=[C:35]([CH2:34][CH2:33][C:29]5[CH:28]=[C:27]([O:26][CH3:25])[CH:32]=[CH:31][N:30]=5)[NH:44][C:38]4=[N:39][CH:40]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1

Komponenten

11

Edukt 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 684087534-Bromo-N-(4-chlorophenyl)-N-methylbenzene-1-sulfonamideHCID 178493175HCID 178493175, Verbindung2×

Produkt 1

HCID 178493162HCID 178493162, VerbindungAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 7611Bis(eta-cyclopentadienyl) ironKatalysatorHCID 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 0.541 g of N-(4-chlorophenyl)-N-methyl-4-bromo-benzenesulfonamide, 0.42 g of bis-(pinacolato)-diboron, 0.025 g of 1,1′-bisdiphenylphosphino)-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 17 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 6 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 30-25:1). Concentration of the chromatographically pure fractions and crystallisation from ethylacetate gives 0.17 g of the title compound as a solid of m.p. 191-192° C. The mass spectrum shows the molecular peak MH+ at 534.3 Da.

Aufarbeitung

  1. customThe tube is sealed again
  2. temperaturethe mixture is heated to 115° under N2 for 6 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 30-25:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-3113385fb3914854bc71a817280a3f4e
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279488B2

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