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Sodium hydride → 2-(5-bromo-2-methyl-2H-indazol-4-yl)cyclopropanecarbonitrile

HRID 1639800
ノート
印刷プレビュー

反応式

HRID 1639800 の反応式
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Br:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH3:19])[N:15]=2)[C:11]=1/[CH:20]=[CH:21]/[C:22]#[N:23]>CS(C)=O.C(OCC)(=O)C>[Br:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH3:19])[N:15]=2)[C:11]=1[CH:20]1[CH2:4][CH:21]1[C:22]#[N:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 59334477(2E)-3-(5-bromo-2-methyl-2H-indazol-4-yl)acrylonitrile

生成物 1

HCID 593346152-(5-bromo-2-methyl-2H-indazol-4-yl)cyclopropanecarbonitrile収率 44.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回
HCID 8857
Ethyl Acetate
溶媒

実験手順

To a suspension of sodium hydride (19.6 mg, 0.490 mmol) in dimethyl sulfoxide (2 mL) was added trimethylsulfoxonium iodide (117 mg, 0.531 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hr. Thereto was added a solution of (2E)-3-(5-bromo-2-methyl-2H-indazol-4-yl)acrylonitrile (107 mg, 0.408 mmol) in dimethyl sulfoxide (2 mL), and the mixture was stirred for 48 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→100/0) to give the title compound (50.0 mg, yield 44%).

後処理

  1. stirringthe mixture was stirred for 48 hr
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→100/0)

出典と根拠

ORDレコード
ord-6fc3f971e45b4037a2c392c6485b8063
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08110585B2

反応ノート

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