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

HRID 1466477Notes

Reaction equation

HRID 1466477 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) prepared in Step A was dissolved in tetrahydrofuran (30 mL), and tetrabutylammonium fluoride 1M solution (5.2 mL, 5.2 mmol) was added in drops thereto at 0° C. After completion of the reaction, the reaction mixture was diluted with water, 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 (1.2 g, Yield 100%).

Workup

  1. customat 0° C
  2. customAfter completion of the reaction
  3. extractionextracted 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-026cdf792ce2417ebb470507961ab73f
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

Loading…