Methyl iodide → ethyl 1-methyl-1H-indole-2-carboxylate

HRID 1601071Notes

Reaction equation

HRID 1601071 reaction equation
I[CH3:2].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[H-].[Na+]>C1COCC1>[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 143368ethyl 1-methyl-1H-indole-2-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodomethane (4.98 mL, 80 mmol) was added dropwise to a mixture containing ethyl indole-2-carboxylate (1.89 g, 10 mmol) and sodium hydride (1.2 g, 60% dispersion, prewashed by hexane) in anhydrous THF (60 mL) in a flame dried flask under argon at 0° C. After 4 h at RT the reaction was concentrated on the rotavap. The residue was taken into EtOAc and washed sequentially with H2O and saturated NaCl. Drying (MgSO4) and concentration gave the title compound (1.01 g, 50%) as a pale yellow solid.

Workup

  1. customdried flask under argon at 0° C
  2. concentrationAfter 4 h at RT the reaction was concentrated on the rotavap
  3. washwashed sequentially with H2O and saturated NaCl
  4. customDrying
  5. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-841c913a60a44bbd9348c5702025fab6
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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