Methyl iodide → methyl N-methyl-4,5,6-trimethoxyindole-2-carboxylate

HRID 720333Notes

Reaction equation

HRID 720333 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[CH:13]=[C:14]([N:19]=[N+]=[N-])[C:15]([O:17][CH3:18])=[O:16].[CH3:22]C(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.IC>C1C=CC=CC=1.O>[CH3:22][N:19]1[C:5]2[C:4](=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[CH:13]=[C:14]1[C:15]([O:17][CH3:18])=[O:16]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 86587494Methyl 3-(2,3,4-trimethoxyphenyl)-2-azidopropenoate

Product 1

HCID 21891561methyl N-methyl-4,5,6-trimethoxyindole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Methyl 3-(2,3,4-trimethoxyphenyl)-2-azidopropenoate (799 mg), potassium tert-butoxide (438 mg) and 18-crown-6(71 mg) were dissolved in dry benzene (60 mL), and the solution was stirred for 15 minutes. Iodomethane (0.28 mL) was then added, and the mixture was stirred overnight. Water was added to the reaction mixture to conduct extraction with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionextraction with ethyl acetate
  3. washThe resultant organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d996a062b151461d9f4e7f84c0228c9b
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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