Potassium Iodide → HCID 28881253, compound

HRID 549379Notes

Reaction equation

HRID 549379 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.Br[CH2:12][C:13]([O-:15])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[C:24](#N)[CH3:25]>C(OCC)(=O)C>[CH2:24]([O:15][C:13](=[O:14])[CH2:12][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])[CH3:25]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 6226BromoacetateHCID 6342AcetonitrileHCID 72242-MethylindoleHCID 10796Cesium carbonate

Product 1

HCID 28881253HCID 28881253, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methyl-1H-indole (1.0 g, 7.6 mmol) in acetonitrile (25 mL) was treated with 2-bromoacetate (2.54 mL, 22.9 mmol), cesium carbonate (2.10 g, 11.4 mmol) and potassium iodide (253 mg, 1.52 mmol) and the resulting mixture was stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and concentrated, and the residue was purified to give (2-methyl-indol-1-yl)-acetic acid ethyl ester (1.36 g, 82% yield). LCMS (m/z): 218.1 (M+1).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified

Sources & evidence

ORD record
ord-4a055437874c42678fffdf958803417e
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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