Potassium Iodide → 5-(1-Ethoxycarbonyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966499

Reaction equation

HRID 966499 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[CH:8][C:7]([OH:21])=[CH:6][CH:5]=2.[CH2:22]([O:24][C:25](=[O:30])[C:26](Br)([CH3:28])[CH3:27])[CH3:23].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:14]([O:13][C:11]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:21][C:26]([C:25]([O:24][CH2:22][CH3:23])=[O:30])([CH3:28])[CH3:27])[CH:8]=2)[NH:3][C:2]=1[CH3:1])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester

Product 1

HCID 233938615-(1-Ethoxycarbonyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl EsterYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methyl-3-benzyloxycarbonyl-5-hydroxyindole (10.0 g, 35.54 mmol, 1.0 eq) was dissolved in acetonitrile (250 mL), followed by ethyl-2-bromo-isobutyrate (7.63 g, 39.10 mmol, 2.0 eq). Potassium carbonate (9.82 g, 71.08 mmol, 8.7 eq) was also added followed by potassium iodide (catalytic amount). The reaction mixture was refluxed for 24 hours. The reaction mixture was washed with brine and extracted with ethyl acetate (3×100 mL) and dried over sodium sulfate. The product was chromatographed in a hexane to hexane/ethyl acetate 7:3. 6.88 g of the product was obtained, 48% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. washThe reaction mixture was washed with brine
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe product was chromatographed in a hexane to hexane/ethyl acetate 7:3

Sources & evidence

ORD record
ord-cb44264314ca42fba20b1323365f41f1
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Linked notes

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