Ethyl Bromide → 6-Ethoxy-1H-indole

HRID 1988973Notes

Reaction equation

HRID 1988973 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:11](Br)[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:11]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1)[CH3:12]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 5245086-Hydroxyindole

Product 1

HCID 5267696-Ethoxy-1H-indole

Procedure

6-Hydroxyindole (1.0 equivalents) is dissolved in dry, degassed acetone. EtBr (5.0 equivalents) and Cs2CO3 (2.5 equivalents) are added, and the resulting solution is stirred for 18 hours. The reaction mixture is filtered through a Celite plug. The solvent is evaporated, and the product is purified by flash chromatography (MeOH:CH2Cl2, 5:95) to yield the title compound.

Workup

  1. customin dry
  2. customdegassed acetone
  3. filtrationThe reaction mixture is filtered through a Celite plug
  4. customThe solvent is evaporated
  5. customthe product is purified by flash chromatography (MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-48deb3eab64a422aafee85cf67bdcffe
Source dataset
uspto-grants-2010_01
Patent number
US07642278B2

Reaction notes

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