Cesium carbonate → 6-(2-methoxyethoxy)-1H-indole

HRID 2361266Notes

Reaction equation

HRID 2361266 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:10])[CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:12][CH2:13][O:14][CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.CCCCCC>CN(C=O)C>[CH3:15][O:14][CH2:13][CH2:12][O:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][NH:1]2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 5245086-HydroxyindoleHCID 21226206Ethyl acetate hexane

Product 1

HCID 679948936-(2-methoxyethoxy)-1H-indoleYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1H-indol-6-ol (4.0 g, 30.0 mmol), 1-bromo-2-methoxyethane (3.53 mL, 37.6 mmol), and cesium carbonate (11.75 g, 36.1 mmol) in DMF (50 mL) was heated at 75° C. for 16 hr. DMF was removed under vacuum with a oil pump. The residue was diluted with ethyl acetate (200 mL), washed sequentially with 1 N NaOH solution (50 mL), water (2×50 mL), and brine (50 mL). The organic solution was dried over anhydrous MgSO4 and concentrated under vacuum. The desired product (4.68 g, 21.54 mmol, 71.7% yield) was isolated as a white solid by ISCO (300 g silica gel, solid loading, 10-50% ethyl acetate/hexane).

Workup

  1. customDMF was removed under vacuum with a oil pump
  2. additionThe residue was diluted with ethyl acetate (200 mL)
  3. washwashed sequentially with 1 N NaOH solution (50 mL), water (2×50 mL), and brine (50 mL)
  4. dry with materialThe organic solution was dried over anhydrous MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9844e8c145a346af8cab9c07e70fe439
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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