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

HRID 1466476Notes

Reaction equation

HRID 1466476 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b1ed735a68b042d390336cad4c215686
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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