Cesium carbonate → 5-(2-methoxyethoxy)-1H-indole

HRID 1527183Notes

Reaction equation

HRID 1527183 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:17][O:18][CH2:19][CH2:20]Br>CC(C)=O>[CH3:17][O:18][CH2:19][CH2:20][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 160545-HydroxyindoleHCID 809722-Bromoethyl methyl ether

Product 1

HCID 103525375-(2-methoxyethoxy)-1H-indole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-hydroxyindole (5 g, 15 mmol) was dissolved in acetone (75 mL), cesium carbonate (5.38 g, 16.5 mmol) and 2-bromoethyl methyl ether (1.55 mL, 16.5 mmol) were added and the reaction mixture was stirred at reflux under nitrogen overnight. Acetone was concentrated. The residue was dissolved in water and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 7/3) to give the desired material. TLC, Rf (c-hexane/EtOAc 1:1)=0.6; MS (LC-MS): 192.1 [M+H]+, 214.0 [M+Na]+, 405.1 [2M+Na]+; tR (HPLC conditions f): 1.56 min.

Workup

  1. temperatureat reflux under nitrogen overnight
  2. concentrationAcetone was concentrated
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted twice with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 7/3)

Sources & evidence

ORD record
ord-71222328413d4a1e9da2c81a9008df67
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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