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
Under a nitrogen atmosphere 0.29 g (4.6 mmol) sodium cyanoborohydride were added batchwise to 0.54 g (4.0 mmol) 6-fluoroindole in 5.0 mL glacial acetic acid and the mixture was stirred for 30 min. Then the reaction mixture was poured onto a 4N aqueous sodium hydroxide solution and extracted with EtOAc. The combined organic phases were washed several times with saturated sodium hydrogen carbonate solution, dried on sodium sulphate and evaporated down.
Workup
- extractionextracted with EtOAc
- washThe combined organic phases were washed several times with saturated sodium hydrogen carbonate solution
- customdried on sodium sulphate
- customevaporated down
Sources & evidence
- ORD record
- ord-5be21d4c530342cc93a44e37b2e1b052
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829006B2
Reaction notes
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