Methyl iodide → HCID 57675476, compound

HRID 490755Notes

Reaction equation

HRID 490755 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)[CH3:6])[CH3:2].[Li+].[CH3:26]C([N-]C(C)C)C.CI>C1COCC1>[CH2:1]([O:3][C:4](=[O:24])[C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)([CH3:26])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamide2×HCID 19097360HCID 19097360, compound

Product 1

HCID 57675476HCID 57675476, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-benzyloxy-indol-1-yl)-propionic acid ethyl ester (20 g, 61.5 mmol) in THF (180 mL) is added LDA (2.0 M toluene, 37 mL) dropwise at −78° C. After the addition of LDA, the mixture is stirred for 30 min, then methyl iodide (8.77 g, 122.6 mmol) is added. The reaction mixture is allowed to warm to room temperature, after stirred for 2 hrs, quenched by water, extracted with ethyl acetate, dried over sodium sulfate. Concentration yields the title compound.

Workup

  1. stirringafter stirred for 2 hrs
  2. customquenched by water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-65ce27dccda64b219e5fa218c11cea27
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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