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Triethylamine → 5-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole

HRID 1466476
ノート
印刷プレビュー

反応式

HRID 1466476 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Cl:11])=[CH:4][C:3]=1I.[C:13]1([C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Li+].C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:11][C:5]1[CH:4]=[C:3]2[C:2](=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=1)[NH:1][C:20]([Si:21]([CH3:24])([CH3:22])[CH3:23])=[C:19]2[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 1374641-Phenyl-2-(trimethylsilyl)acetyleneHCID 433294Lithium ChlorideHCID 121435644-Chloro-2-iodo-6-nitroaniline

生成物 1

HCID 684760765-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole収率 87%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

2-Amino-5-chloro-3-nitro-phenyliodide (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100□. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%).

後処理

  1. temperatureunder heating for 3 h to 100□
  2. additionwas added to the reaction mixture, which
  3. extractionwas then extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-b1ed735a68b042d390336cad4c215686
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09000028B2

反応ノート

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