Ammonium fluoride → 5-Ethyl-1H-indole

HRID 1454062Notes

Reaction equation

HRID 1454062 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([Si](C(C)C)(C(C)C)C(C)C)[CH:7]=[CH:6]2)[CH3:2].[F-].[NH4+]>C1COCC1.CO>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)[CH3:2]

Participants

5

Reactant 2

HCID 25516Ammonium fluorideHCID 184500545-Ethyl-1-triisopropylsilanyl-1H-indole

Product 1

HCID 123992105-Ethyl-1H-indole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The Indole 9 (2.2 g, 7.29 mmol) was dissolved in THF (20 mL) and a solution of ammonium fluoride (NH4F; 1.4 g, 37.8 mmol) in MeOH (20 mL) was added and stirred for 72 hours at room temperature. The solvent was evaporated and the residue was dissolved in ethyl acetate. The organic layer was washed with 2N H3PO4, dried over MgSO4, filtered and evaporated to give compound 10 as an off white solid (1.06 g; M+1=146.2).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with 2N H3PO4
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4759c4e1179d42e9ac10f5d158cad7b8
Source dataset
uspto-grants-2009_01
Patent number
US07476746B2

Reaction notes

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