Methyl iodide → 2-(1-ethyl-6-fluoro-4-methoxy-1H-indol-3-yl)ethanol

HRID 1404152Notes

Reaction equation

HRID 1404152 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([F:12])[CH:8]=[C:7]([OH:13])[C:6]=2[C:5]([CH2:14][CH2:15][OH:16])=[CH:4]1)[CH3:2].[C:17](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([O:13][CH3:17])[CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([CH2:14][CH2:15][OH:16])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 669272011-ethyl-6-fluoro-3-(2-hydroxyethyl)-1H-indol-4-ol

Product 1

HCID 669270822-(1-ethyl-6-fluoro-4-methoxy-1H-indol-3-yl)ethanolYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

39-2 (318 mg, 1.43 mmol) was dissolved in DMF (5 mL) and then potassium carbonate (236 mg, 1.71 mmol) and methyl iodide (98 uL, 1.56 mmol) were added. The reaction mixture was stirred at room temperature overnight, concentrated under vacuum and then water added. A solid was filtered to afford 39-3 (313 mg, 90%) as a light purple solid. LCMS: calc 326.2. found 327.1 [MH]+.

Workup

  1. concentrationconcentrated under vacuum
  2. additionwater added
  3. filtrationA solid was filtered

Sources & evidence

ORD record
ord-2dc35020ef594c509e316379bd578231
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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