Trifluoroacetic acid → 5-cyclopropyl-2-phenyl-1H-indole

HRID 2400277Notes

Reaction equation

HRID 2400277 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:16][CH2:15]2)=[CH:10][C:9]=1[CH2:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:14]1([C:11]2[CH:10]=[C:9]3[C:8](=[CH:13][CH:12]=2)[NH:7][C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17]3)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731722Tert-butyl[4-cyclopropyl-2-(2-oxo-2-phenylethyl)phenyl]carbamate

Product 1

HCID 696709445-cyclopropyl-2-phenyl-1H-indoleYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[4-cyclopropyl-2-(2-oxo-2-phenylethyl)phenyl]carbamate (561 mg) in dichloromethane (8 mL) was added dropwise trifluoroacetic acid (1.6 mL) under ice-cooling. The mixture was heated to room temperature, and then stirred for 23 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution to separate the organic layer. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (317 mg). 1H-NMR (CDCl3) δ ppm: 0.65-0.75 (2H, m), 0.85-1.00 (2H, m), 1.95-2.10 (1H, m), 6.70-6.80 (1H, m), 6.90-7.00 (1H, m), 7.25-7.50 (5H, m), 7.60-7.70 (2H, m), 8.24 (1H, br s).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  4. customto separate the organic layer
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c46d49bd7d2b4c32b3c3d6cc355df3b6
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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