Potassium Carbonate → HCID 22340427, compound

HRID 585311Notes

Reaction equation

HRID 585311 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]3)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 22340427HCID 22340427, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 5-hydroxy-1H-indole-2-carboxylate (508 mg, 2.48 mmol), 1-bromo-4-(bromomethyl)benzene (681 mg, 2.72 mmol) and potassium carbonate (684 mg, 4.95 mmol) in acetonitrile (12 ml) was stirred at 80° C. for 3 hours. The solvent was distilled off under reduced pressure, ethyl acetate was added to the resulting oil, the mixture was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent was concentrated under reduced pressure, the resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate), and converted into powders with isopropyl ether to obtain ethyl 5-[(4-bromobenzyl)oxy]-1H-indole-2-carboxylate (565 mg).

Workup

  1. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  2. additionwas added to the resulting oil
  3. washthe mixture was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter the solvent was concentrated under reduced pressure
  6. customthe resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-13aa4212f35a46e5951a7a3d44bc7b68
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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