Methyl iodide → Methyl 4-methoxy-1H-indole-6-carboxylate

HRID 2235103Notes

Reaction equation

HRID 2235103 reaction equation
CI.[CH3:3][O:4][C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[C:9]([OH:16])[CH:8]=1)=[O:6].[C:17](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:3][O:4][C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[C:9]([O:16][CH3:17])[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13644880Methyl 4-hydroxy-1H-indole-6-carboxylate

Product 1

HCID 12140116Methyl 4-methoxy-1H-indole-6-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (0.72 mL, 11.5 mmol, 1.1 equiv.) was added dropwise, over 10 minutes, to a stirred solution of 4-hydroxy-1H-indole-6-carboxylic acid methyl ester (2 g, 10.5 mmol, 1 equiv.) and potassium carbonate (1.3 g, 15.7 mmol, 1.5 equiv.) in acetone (20 mL) at room temperature and the mixture was heated at reflux for 16 hours. The solvent was removed under vacuum, the residue dissolved in ethyl acetate (20 mL) and washed with saturated aqueous solution of NaHCO3 (20 mL) and water (20 mL). The organic layer was dried over Na2SO4 and the solvent removed under vacuum to afford 4-methoxy-1H-indole-6-carboxylic acid methyl ester, 1.1 g (49% yield). LC @215 nm; Rt 1.23: 91%, m/z (ES+): 206 (M+H+.); δH (400 MHz; MeOD) 7.74 (1H, s), 7.15 (1H, m), 7.03 (1H, d), 6.46 (1H, m), 3.86 (3H, s), 3.80 (3H, s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue dissolved in ethyl acetate (20 mL)
  5. washwashed with saturated aqueous solution of NaHCO3 (20 mL) and water (20 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-dd74f66f55e64709bdf2db7dc3f53997
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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