Sodium Hydroxide → 6-fluoro-2,3-dihydro-1H-indole

HRID 1640257Notes

Reaction equation

HRID 1640257 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]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3512786-FluoroindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 2604006-fluoro-2,3-dihydro-1H-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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 at RT. 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

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed several times with saturated sodium hydrogen carbonate solution
  3. customdried on sodium sulphate
  4. customevaporated down

Sources & evidence

ORD record
ord-f6cefcf85e8441f380ea323deef35e0e
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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