Indole → 1-Phenyl-1H-indole

HRID 590966

Reaction equation

HRID 590966 reaction equation
[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

Participants

6

Reactant 3

HCID 798IndoleHCID 10796Cesium carbonateHCID 11575Iodobenzene

Product 1

HCID 1820291-Phenyl-1H-indoleYield 86.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-8d930df7469e409fa08d44b1df35d058
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Linked notes

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