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

HRID 559500

反応式

HRID 559500 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 167845palladium(II) acetate触媒HCID 180Acetone溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0edeac393455446c8c1f13128fb177e6
出典データセット
uspto-grants-2011_11
特許番号
US08063080B2

関連ノート

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