Water → methyl 1H-indole-5-carboxylate

HRID 539934Notes

Reaction equation

HRID 539934 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([OH:3])=[O:2].[C:13]([O-])(O)=O.[Na+].CI.O>CN(C=O)C.CCOC(C)=O>[CH3:13][O:2][C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 742801H-Indole-5-Carboxylic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 2737635methyl 1H-indole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-carboxyindole (32.2 g, 0.2 mol), NaHCO3 (53.36 g, 0.64 mol), methyl iodide (122.22 g, 0.86 mol) in 60 mL of DMF were stirred at RT for 2 days. Water and EtOAc are added, and the organic layer was washed with bicarbonate solution, dried and concentrated to obtain 5-(methoxycarbonyl)indole. 1H NMR (DMSO) δ: 11.44 (s, 1H), 8.22 (s, 1H), 7.68 (d, J=8.4 Hz, 1H), 7.37˜7.47 (m, 2 H), 6.56 (d, J=2.0 Hz, 1H), 3.80 (s, 3H). MS (ESI) m/e (M+H+): 176.

Workup

  1. washthe organic layer was washed with bicarbonate solution
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7b13bbd824cc4533b87415573fa00b36
Source dataset
uspto-grants-2014_10
Patent number
US08871759B2

Reaction notes

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