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

HRID 910120Notes

Reaction equation

HRID 910120 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-fluoroindole (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-4977020c7eb742069bceb6825a22f711
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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