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

HRID 1802824
Notes
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Reaction equation

HRID 1802824 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Amino-5-chloro-3-nitro-phenyliodide (1.5 g, 4.90 mmol) obtained in Step 1 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL), and thereto 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. The mixture was heated under stirring for 3 hours at 100° C. At the end of reaction, added water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give 5-chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole (1.05 g, Yield 87%).

Workup

  1. temperatureThe mixture was heated
  2. customAt the end of reaction
  3. extractionextracted with ethylacetate
  4. washThe extract was washed with saturated 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 separated by column chromatography

Sources & evidence

ORD record
ord-5461f0e0cb0b41a48773a002496e998f
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08349885B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes