Indole → 1-Phenyl-1H-indole

HRID 590966

反応式

HRID 590966 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:16]1(I)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O.[Cu]I>[C:16]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 798IndoleHCID 10796Cesium carbonateHCID 11575Iodobenzene

生成物 1

HCID 1820291-Phenyl-1H-indole収率 86.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of indole (500 mg, 4.27 mmol), copper(I) iodide (122 mg, 0.64 mmol), cesium carbonate (1.9 g, 6 mmol) and phenyliodide (470 μL, 4.2 mmol) in anhydrous N,N-dimethylformamide (10 mL) was refluxed for 24 hours under a nitrogen atmosphere. The reaction mixture was then filtered and concentrated in vacuo. The residue was partitioned between dichloromethane (30 mL) and water (10 mL). The organic layer was washed with water (2×10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5) to afford the desired product (5a) as a yellow oil (700 mg, 3.62 mmol, 86%).

後処理

  1. temperaturewas refluxed for 24 hours under a nitrogen atmosphere
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between dichloromethane (30 mL) and water (10 mL)
  5. washThe organic layer was washed with water (2×10 mL), brine (10 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5)

出典と根拠

ORDレコード
ord-8d930df7469e409fa08d44b1df35d058
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

関連ノート

読み込み中…