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

HRID 559500

반응식

HRID 559500 반응식
[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

참가 물질

8

반응물 3

HCID 5798BenzimidazoleHCID 11776TriphenylphosphineHCID 6693044-bromo-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide

생성물 1

HCID 160399334-(1H-Benzimidazol-2-yl)-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide수율 2.2%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 167845palladium(II) acetate촉매HCID 180Acetone용매HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-0edeac393455446c8c1f13128fb177e6
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063080B2

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