Tetrabutylammonium Fluoride → Indole

HRID 2109984Notes

Reaction equation

HRID 2109984 reaction equation
CCCC[N+:5]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])CCCC.[F-]>C1COCC1.CCOC(C)=O>[NH:5]1[C:10]2[C:16](=[CH:17][CH:13]=[CH:12][CH:11]=2)[CH:15]=[CH:14]1

Participants

4

Reactant 1

HCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 798Indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Intermediate 6 (250 mg, 0.4 mmol) in THF (10 mL) was a TBAF solution (1.0 M in THF, 10 mL, 10 mmol) and the resulting solution was heated to reflux for 22 hrs. Upon cooling, the reaction was diluted with EtOAc (250 mL), washed with H2O (7×15 mL) and brine, dried over Na2SO4, filtered, and concentrated to give the intermediate deprotected indole as a brown foam (252 mg, LC/MS (ESI) retention time: 2.01 min, m/z 501 (MH+)) which was used in the next step without further purification.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 22 hrs
  3. temperatureUpon cooling
  4. washwashed with H2O (7×15 mL) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-593a1828be58447aa0d265861b80e894
Source dataset
uspto-grants-2009_04
Patent number
US07517872B2

Reaction notes

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