Potassium Carbonate → (2-Methyl-1H-indol-4-yloxy)-acetic acid benzyl ester

HRID 1445887Notes

Reaction equation

HRID 1445887 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[NH:6]2.[CH2:12]([O:19][C:20](=[O:23])[CH2:21]Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:19][C:20](=[O:23])[CH2:21][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[NH:6]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 5902254-Hydroxy-2-methylindole

Product 1

HCID 58765424(2-Methyl-1H-indol-4-yloxy)-acetic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxy-2-methylindole (3.0 g, 0.02 mole), bromo-acetic acid benzyl ester (4.6 g, 0.02 mole), potassium carbonate (2.8 g, 0.02 mole) in acetone was refluxed for 48 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (10:1 Hex:EtOAc) to afford intermediate (2). Yield: 3.5 g, 58%.

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography (10:1 Hex:EtOAc)

Sources & evidence

ORD record
ord-af9a5eb9069141e4a752b31f69239149
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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