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

HRID 1725416Notes

Reaction equation

HRID 1725416 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-indoleYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

  1. extractionextract with ethyl acetate
  2. washWash the combined organic phases with saturated aqueous sodium bicarbonate
  3. concentrationConcentrated under reduced pressure

Sources & evidence

ORD record
ord-be1f283c97b6452ea57b9c6ea5ca1bc8
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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