Cesium carbonate → HCID 66743305, compound

HRID 2364065Notes

Reaction equation

HRID 2364065 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.Br[CH2:19][C:20]1C=C[CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+]>O.CO.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][C:13]2[CH:19]=[CH:20][CH:21]=[C:22]([N+:26]([O-:28])=[O:27])[CH:23]=2)[CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 56965789Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

Product 1

HCID 66743305HCID 66743305, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate (500 mg, 1.51 mmol), 1-(bromomethyl)-3-nitrobenzene (490 mg, 2.27 mmol), cesium carbonate (1.23 g, 3.78 mmol) and DMF (10 mL) was stirred at 70° C. for 1 h. Then, water was 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 purified by column chromatography (Purif, silica gel, hexane to 80:20 hexane/EtOAc) to give a yellow oil. A mixture of this oil, MeOH (5 mL), potassium carbonate (500 mg) and water (2.5 mL) was stirred at room temperature for 0.5 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 title compound (495 mg, 88%) was obtained as a yellow 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. customthe residue was purified by column chromatography (Purif, silica gel, hexane to 80:20 hexane/EtOAc)
  9. customto give a yellow oil
  10. stirringwas stirred at room temperature for 0.5 h
  11. customAfter removal of the solvent at reduced pressure
  12. extractionthe organic materials were extracted with EtOAc
  13. washThe combined extracts were washed with brine
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. customAfter removal of the solvent at reduced pressure

Sources & evidence

ORD record
ord-22779038b81d41f6af08b02834fde3db
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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