Cesium carbonate → HCID 66744226, compound

HRID 2364085Notes

Reaction equation

HRID 2364085 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.Br[CH2:20][C:21]1[CH:22]=[N:23][CH:24]=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(N(C)C)=O>O>[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:24]=[N:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 56965789Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

Product 1

HCID 66744226HCID 66744226, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate (100 mg, 1.51 mmol), 3-(bromomethyl)pyridine hydrobromide (457 mg, 1.81 mmol), cesium carbonate (1.72 g, 5.29 mmol) and DMA (15 mL) was stirred at 80° C. for 2 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 dissolved in MeOH (5 mL). To the solution were added potassium carbonate (500 mg) and water (2.5 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 50:50 hexane/EtOAc) to give the title compound (260 mg, 53%) as a yellow solid:

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 (5 mL)
  9. additionTo the solution were added potassium carbonate (500 mg) and water (2.5 mL)
  10. stirringThe mixture was stirred at room temperature for 2 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
  17. customthe residue was purified by column chromatography (Purif, silica gel, hexane to 50:50 hexane/EtOAc)

Sources & evidence

ORD record
ord-aaccf5c171904529946f45ab1ca9e18e
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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