Water → HCID 18007583, compound

HRID 1375672Notes

Reaction equation

HRID 1375672 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.Br[CH2:14][CH2:15][OH:16].O>CS(C)=O>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:14][CH2:15][OH:16])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 14797Potassium HydroxideHCID 6764936-Bromoindole

Product 1

HCID 18007583HCID 18007583, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

KOH (571 mg, 10.2 mmol) was stirred in 5 mL of anhydrous DMSO at room temperature. 6-Bromoindole (500 mg, 2.55 mmol) was added as solid. After 30 min, 2-bromoethanol (181 μL, 2.55 mmol) was added to the green solution, which was then stirred at room temperature overnight. Water was then added and the reaction mixture was extracted with ethyl acetate (2×25 mL). The organic layer was then washed with water and brine, dried over Na2SO4, evaporated in vacuo. MPLC purification of the crude product provided the titled compound as a light brown oil (344 mg, 56% yield).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (2×25 mL)
  2. washThe organic layer was then washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customMPLC purification of the crude product

Sources & evidence

ORD record
ord-831a23628a74442095f26ad818a74615
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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