Indole → 1-Phenyl-1H-indole

HRID 590966

반응식

HRID 590966 반응식
[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

참가 물질

6

반응물 3

HCID 798IndoleHCID 10796Cesium carbonateHCID 11575Iodobenzene

생성물 1

HCID 1820291-Phenyl-1H-indole수율 86.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-8d930df7469e409fa08d44b1df35d058
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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