Water → HCID 90092928, compound

HRID 1774598Notes

Reaction equation

HRID 1774598 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:13][C:14]([F:17])([F:16])[F:15])(=O)=O.[Br:20][C:21]1[C:22]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)=[N:23][NH:24][C:25]=1[CH:26]=[O:27].O>CN(C)C=O>[Br:20][C:21]1[C:22]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)=[N:23][N:24]([CH2:13][C:14]([F:15])([F:16])[F:17])[C:25]=1[CH:26]=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 90092931HCID 90092931, compound

Product 1

HCID 90092928HCID 90092928, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Cesium carbonate (1.56 g, 4.78 mmol) and 2,2,2-triflouroethyl trifluoromethanesulfonate (0.92 mL, 6.38 mmol) were added to a solution of 4-bromo-3-(thiophen-2-yl)-1H-pyrazole-5-carbaldehyde (34c) (0.82 g, 3.19 mmol) in N,N-dimethylformamide (15 mL). The reaction mixture was stirred at 100° C. for 50 minutes. Water (20 mL) was added, and the mixture was extracted with ethyl acetate (2×40 mL). The organic layer was washed with brine (50 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 100/0 to 94/6), to provide 4-bromo-3-(thiophen-2-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazole-5-carbaldehyde (34d) (350 mg, 1.03 mmol, 32%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×40 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 100/0 to 94/6)

Sources & evidence

ORD record
ord-81864847e9714e00a7ee733c68571848
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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