Potassium Carbonate → HCID 10377032, compound

HRID 1769881Notes

Reaction equation

HRID 1769881 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>CC(C)=O>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:1][C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 5245086-Hydroxyindole

Product 1

HCID 10377032HCID 10377032, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-Hydroxyindole (0.90 g, 6.8 mmol) and potassium carbonate (1.04 g, 7.5 mmol), were suspended in 13 mL of acetone. 4-Fluorobenzyl bromide (0.93 mL, 7.5 mmol, prefiltered through basic alumina) was added dropwise via syringe. The reaction mixture was heated at reflux under N2 atmosphere for 24 hours. The reaction mixture was cooled to ambient temperature and partitioned between H2O and methylene chloride. The aqueous phase was extracted twice with methylene chloride. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by chromatography on silica gel to give 6-(4-fluorophenylmethoxy)indole (1.4 g, 88%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under N2 atmosphere for 24 hours
  3. custompartitioned between H2O and methylene chloride
  4. extractionThe aqueous phase was extracted twice with methylene chloride
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-004ab4c92bc7449482ff2c0fe611a2b7
Source dataset
uspto-grants-1995_01
Patent number
US05382670

Reaction notes

Loading…