Potassium Cyanide → HCID 68445800, compound

HRID 2233169Notes

Reaction equation

HRID 2233169 reaction equation
Br[CH2:2][C:3]1[C:4]([F:15])=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[N:8]2.[C-:16]#[N:17].[K+]>CN(C)C=O>[F:15][C:4]1[C:3]([CH2:2][C:16]#[N:17])=[C:12]2[C:7](=[CH:6][CH:5]=1)[N:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11]2

Participants

4

Reactant 2

HCID 9032Potassium Cyanide2×HCID 67548259HCID 67548259, compound

Product 1

HCID 68445800HCID 68445800, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8-bromomethyl-7-fluoro-2-(methyloxy)quinoxaline (5.89 g, 20 mmol) and potassium cyanide (3.2 g, 49 mmol) in dimethylformamide (125 ml) was heated at 50° C. for approx. 40 h. More potassium cyanide (0.8 g) was added and heating continued at 60° C. for ˜8 h. The mixture was then evaporated and the residue was dissolved in dichloromethane and washed with water. The aqueous phase was extracted twice with dichloromethane and the combined organic fractions were dried and evaporated. Chromatography on silica (300 g), eluting with 0-25% ethyl acetate/hexane gave product (2.47 g, 57%).

Workup

  1. temperatureheating
  2. customThe mixture was then evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with water
  5. extractionThe aqueous phase was extracted twice with dichloromethane
  6. customthe combined organic fractions were dried
  7. customevaporated
  8. washChromatography on silica (300 g), eluting with 0-25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-79db6c8e988e4ce6baa59c7506a734dd
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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