Iodoethane → HCID 66743792, compound

HRID 2364038Notes

Reaction equation

HRID 2364038 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([NH:11][C:12](=O)[C:13](F)(F)F)[CH:3]=1.ICC.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+]>O.CCOC(C)=O.CN(C=O)C>[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([NH:11][CH2:12][CH3:13])[CH:3]=1

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 56965789Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

Product 1

HCID 66743792HCID 66743792, compoundYield 97.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate (3.18 g, 9.58 mmol), iodoethane (3.8 mL, 47.9 mmol), cesium carbonate (7.80 g, 24.0 mmol) and DMF (10 mL) was stirred at 70° C. for 3 h. Then, water and EtOAc were added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was dissolved in MeOH (15 mL). To the solution were added potassium carbonate (3.97 g, 28.7 mmol) and water (10 mL). The mixture was stirred at room temperature for 2 h. After removal of the solvent at reduced pressure, the organic materials were extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, hexane to 90:10 hexane/EtOAc) to give the title compound (2.46 g, 97%) as a light green oil:

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe organic materials were extracted with EtOAc
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customAfter removal of the solvent at reduced pressure
  8. dissolutionthe residue was dissolved in MeOH (15 mL)
  9. stirringThe mixture was stirred at room temperature for 2 h
  10. customAfter removal of the solvent at reduced pressure
  11. extractionthe organic materials were extracted with EtOAc
  12. washThe combined extracts were washed with brine
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. customAfter removal of the solvent at reduced pressure
  16. customthe residue was purified by column chromatography (Purif, silica gel, hexane to 90:10 hexane/EtOAc)

Sources & evidence

ORD record
ord-e7badc24c7f0464b94fbe7eee8ecef4d
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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