N-Fluorobenzenesulfonimide → 4-(2,2-dimethylpropyl)-2-{fluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 216411ノート

反応式

HRID 216411 の反応式
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][C:12]([CH3:43])([CH2:41]C)[CH2:13][C:14]1[N:15]=[C:16]([C:25](=[O:40])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][N:34]=3)=[CH:29][CH:28]=2)[N:17]([S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH:18]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:54])(=O)=O)=CC=1>O1CCCC1>[CH3:11][C:12]([CH3:43])([CH3:41])[CH2:13][C:14]1[N:15]=[C:16]([C:25](=[O:40])[CH:26]([F:54])[C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][N:34]=3)=[CH:29][CH:28]=2)[N:17]([S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH:18]=1

参加物

5

反応物 3

HCID 588007N-FluorobenzenesulfonimideHCID 2733832Lithium HexamethyldisilazideHCID 667056774-(2,2-dimethylbutyl)-2-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

生成物 1

HCID 866385164-(2,2-dimethylpropyl)-2-{fluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Lithium hexamethyldisilazide (1 M in tetrahydrofuran) (92 mL, 0.09 mmol) was added to a −78° C. solution of 4-(2,2-dimethylbutyl)-2-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (35 mg, 0.08 mmol) in tetrahydrofuran (2 mL). After stirring at −78° C. for 10 min, a solution of N-fluorobenzenesulfonimide (36 mg, 0.11 mmol) in tetrahydrofuran (1 mL) was added. The reaction was allowed to warm to ambient temperature, quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 4-(2,2-dimethylpropyl)-2-{fluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

後処理

  1. temperatureto warm to ambient temperature
  2. customquenched with water
  3. extractionextracted with methylene chloride and ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-434711975a934e50bfeb7b264d9c10b9
出典データセット
uspto-grants-2012_06
特許番号
US08193228B2

反応ノート

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