Methyl iodide → Methyl 3-(methoxymethyl)-1H-indole-5-carboxylate

HRID 1015441Notes

Reaction equation

HRID 1015441 reaction equation
[OH:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1.[CH3:16]I>C(#N)C.[Ag]=O>[CH3:16][O:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6328Methyl iodide2×HCID 67300394Methyl 3-(hydroxymethyl)-1H-indole-5-carboxylate

Product 1

HCID 67300506Methyl 3-(methoxymethyl)-1H-indole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalyst3×HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A 327 mg portion of methyl 3-(hydroxymethyl)-1H-indole-5-carboxylate was dissolved in 9 ml of acetonitrile, mixed with 385 mg of silver oxide and 3.6 ml of methyl iodide and stirred at 80° C. for 5 hours. A 385 mg portion of silver oxide was further added thereto and stirred overnight at 80° C. A 385 mg portion of silver oxide and 3.6 ml of methyl iodide were further added thereto and stirred at 80° C. for 9 hours. After cooling to room temperature, the insoluble matter was removed, the solvent was evaporated, and then the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6 to 1:5 to 1:4) to obtain 143 mg of methyl 3-(methoxymethyl)-1H-indole-5-carboxylate as a pale yellow solid.

Workup

  1. stirringstirred overnight at 80° C
  2. stirringstirred at 80° C. for 9 hours
  3. temperatureAfter cooling to room temperature
  4. customthe insoluble matter was removed
  5. customthe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6 to 1:5 to 1:4)

Sources & evidence

ORD record
ord-71d787d2a80b42b096f37d813ecec770
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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