Methyl iodide → methyl 4-methoxy-1-methyl-1H-indole-2-carboxylate

HRID 2112640Notes

Reaction equation

HRID 2112640 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[NH:9]2.[CH3:18]I>CCCCCC.CN(C=O)C>[CH3:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[N:9]2[CH3:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 688172methyl 4-methoxy-1H-indole-2-carboxylate

Product 1

HCID 4777904methyl 4-methoxy-1-methyl-1H-indole-2-carboxylateYield 96.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% dispersion in mineral oil, 0.3 g, 7.3 mmole) was washed with hexane then suspended in anhydrous DMF (16 mL). The mixture was cooled to 0° C. and methyl 4-methoxy-1H-indol-2-carboxylate (1.0 g, 4.87 mmole) was added. The mixture was stirred under argon for 10 min, then MeI (13 mL, 20 mmole) was added, and the thick slurry was stirred at RT for 2.5 hr. The reaction was quenched with 10% NH4Cl (2 mL) and concentrated. The residue was partitioned between H2O and Et2O, and the organic layer was dried over MgSO4 and concentrated to yield the title compound (1.03 g, 96%) as a white solid: MS (ES) m/e 220.2 (M+H)+.

Workup

  1. stirringthe thick slurry was stirred at RT for 2.5 hr
  2. customThe reaction was quenched with 10% NH4Cl (2 mL)
  3. concentrationconcentrated
  4. customThe residue was partitioned between H2O and Et2O
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ace5edeaac6459cbb841b263dbf300c
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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