Ammonium fluoride → 5-Ethyl-1H-indole
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
Product 1
Reagents, catalysts & solvents 2
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
- customThe solvent was evaporated
- dissolutionthe residue was dissolved in ethyl acetate
- washThe organic layer was washed with 2N H3PO4
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-2f9eb7cc2af9493d9449156abe767943
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202266B2
Reaction notes
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