Xenon difluoride → trans-N-{[2-(3-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

HRID 1639859ノート

反応式

HRID 1639859 の反応式
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[N:3]1.[Xe](F)[F:20]>C(#N)C.C(=O)([O-])O.[Na+]>[F:20][C:10]1[N:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[C:8]([C@@H:11]1[CH2:13][C@H:12]1[CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:7][CH:6]=[CH:5]2

参加物

5

反応物 2

HCID 83674Xenon difluorideHCID 59334573trans-N-{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

生成物 1

HCID 59334602trans-N-{[2-(3-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide収率 6%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of trans-N-{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide (400 mg, 1.644 mmol) in acetonitrile (16 mL) was added xenon difluoride (306 mg, 1.808 mmol), and the mixture was stirred under nitrogen atmosphere at room temperature for 4.5 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0), HPLC and TLC to give the title compound (24 mg, yield 6%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 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 (NH, ethyl acetate/hexane=50/50→100/0), HPLC and TLC

出典と根拠

ORDレコード
ord-20621d4162a94dc9ad4f6466d5ea554c
出典データセット
uspto-grants-2012_02
特許番号
US08110585B2

反応ノート

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