Methyl iodide → Methyl 5-methoxy-1-methyl-1H-indolecarboxylate

HRID 379543Notes

Reaction equation

HRID 379543 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20][CH3:21])=[O:19])=[CH:12]2.CI>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:1])[C:13]([C:18]([O:20][CH3:21])=[O:19])=[CH:12]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 27281841H-Indole-2-carboxylic acid, 5-methoxy-, methyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 4777906Methyl 5-methoxy-1-methyl-1H-indolecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

100 ml of a 1N solution of potassium tert-butoxide in tetrahydrofuran is added dropwise to a solution, cooled to −20° C., of 0,1 mol of methyl 5-methoxy-1H-indolecarboxylate in tetrahydrofuran. The medium is stirred for 30 minutes at this temperature, followed by dropwise addition of a solution of 0.1 mol of methyl iodide in tetrahydrofuran. Once the addition is complete, the medium is warmed slowly to room temperature, stirred for 1 h at this temperature and filtered. The expected product is obtained after concentration of the solvent.

Workup

  1. additionOnce the addition
  2. stirringstirred for 1 h at this temperature
  3. filtrationfiltered

Sources & evidence

ORD record
ord-dd3316c0050f4fda809ebc84ad09e9b0
Source dataset
uspto-grants-2001_10
Patent number
US06300340B1

Reaction notes

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