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

HRID 1434680

Reaction equation

[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

Participants

Conditions

Temperature: 150 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-11b19ce5401e465389a45aed940ef3c2
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615569B2

Linked notes

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