Benzimidazole → 4-(1H-Benzimidazol-2-yl)-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide

HRID 559500

Reaktionsgleichung

[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:39][C:40]2[S:41][CH:42]=[CH:43][N:44]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1>O1CCOCC1.CC(C)=O.[Cu](I)I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:39][C:40]2[S:41][CH:42]=[CH:43][N:44]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

Benzimidazole (0.313 mmol) and MgO (0.376 mmol) was stirred in 1,4-dioxane (2 mL) for 10 min. at room temp. To the solution, copper iodide (0.627 mmol), palladium acetate (0.016 mmol), triphenylphosphine (0.062 mmol), and 4-bromo-N-thiazol-2-yl-benzenesulfonamide (0.313 mmol) were added. The reaction was sealed and heated to 150° C. After 7 h the reaction was cooled to 120° C. and stirred overnight. The reaction was cooled to room temperature and diluted with acetone. The solution was filtered through Celite and concentrated in vacuo. The crude was purified by reverse phase chromatography to yield 4-(1H-benzoimidazol-2-yl)-N-thiazol-2-yl-benzenesulfonamide (0.007 mmol).

Aufarbeitung

customThe reaction was sealed
temperatureAfter 7 h the reaction was cooled to 120° C.
temperatureThe reaction was cooled to room temperature
filtrationThe solution was filtered through Celite
concentrationconcentrated in vacuo
customThe crude was purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag: ord-0edeac393455446c8c1f13128fb177e6
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08063080B2

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