Trifluoroacetic acid → 5-Chloro-2-isobutylindole

HRID 1191645Notes

Reaction equation

HRID 1191645 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH2:15][C:16](=O)[CH2:17][CH:18]([CH3:20])[CH3:19])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[Cl:14][C:11]1[CH:10]=[C:9]2[C:8](=[CH:13][CH:12]=1)[NH:7][C:16]([CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:15]2

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67684758Tert-butyl[4-chloro-2-(4-methyl-2-oxopentyl)phenyl]carbamate

Product 1

HCID 696707885-Chloro-2-isobutylindoleYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl[4-chloro-2-(4-methyl-2-oxopentyl)phenyl]carbamate (280 mg) in dichloromethane (4 mL) was added trifluoroacetic acid (0.7 mL) at room temperature, and the mixture was stirred for 7 hours. The reaction mixture was diluted with ethyl acetate and stopped the reaction by addition of a saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (166 mg).

Workup

  1. customthe reaction
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-71d549ace18d4ff1a4f4b7d1ef86b882
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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