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

HRID 1639860ノート

反応式

HRID 1639860 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(OCC)(=O)C>[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 12.9%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-{[(1R,2R)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide (100 mg, 0.411 mmol) in acetonitrile (4.1 mL) was added xenon difluoride (76.5 mg, 0.452 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate is 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 (NH, ethyl acetate/hexane=50/50→100/0) and preparative TLC (methanol/ethyl acetate=10/90) to give the title compound (13.9 mg, yield 11%).

後処理

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0) and preparative TLC (methanol/ethyl acetate=10/90)

出典と根拠

ORDレコード
ord-780d952311f74c1a93b3f27e421a2c67
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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