Sodium Hydroxide → 6-fluoro-2,3-dihydro-1H-indole
Reaction equation
C([BH3-])#N.[Na+].[F:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)(=O)C>[F:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][NH:12]2)=[CH:8][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Add sodium cyanoborohydride (5.57 g, 88.78 mmol) to a solution of 6-fluoro-indole (10 g, 73.99 mmol) in acetic acid (100 ml). Stir at room temperature for 30 minutes. Pour the reaction mixture into 5N sodium hydroxide and extract with ethyl acetate. Wash the combined organic phases with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. Concentrated under reduced pressure and subject the residue to silica gel chromatography to provide the desired compound as a colorless oil (7.69 g, 76%).
Workup
- extractionextract with ethyl acetate
- washWash the combined organic phases with saturated aqueous sodium bicarbonate
- concentrationConcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5876ebfc213c4646997de813d5d3e5d2
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08058425B2
Reaction notes
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