Tetrabutylammonium Fluoride → 5-Chloro-3-phenyl-7-nitro-1H-indole

HRID 1802825Notes

Reaction equation

HRID 1802825 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][C:6]([Si](C)(C)C)=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 684760765-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole

Product 1

HCID 684718405-Chloro-3-phenyl-7-nitro-1H-indoleYield 101.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole (1.5 g, 4.35 mmol) obtained in Step 2 was dissolved in tetrahydrofurane (30 mL), and 1 M tetrabutylammoniumfluoride solution (5.2 mL, 5.2 mmol) was added in drops at 0° C. At the end of reaction, the resulting mixture was diluted with 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 using column chromatography to give 5-chloro-3-phenyl-7-nitro-1H-indole (1.2 g, Yield 100%).

Workup

  1. customAt the end of reaction
  2. extractionextracted with ethylacetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was separated

Sources & evidence

ORD record
ord-4599e6e4bc7f485781140124c9c69bd3
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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