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

HRID 74568

Reaction equation

HRID 74568 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. 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-5be21d4c530342cc93a44e37b2e1b052
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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