Water → methyl 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carboxylate

HRID 341523Notes

Reaction equation

HRID 341523 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH2:21][C:22]([F:25])([F:24])[F:23])(=O)=O.O>CN(C=O)C>[F:23][C:22]([F:25])([F:24])[CH2:21][N:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5565652,2,2-Trifluoroethyl MethanesulfonateHCID 178498454HCID 178498454, compound

Product 1

HCID 50896719methyl 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carboxylateYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 1H-pyrazole-3-carboxylate (1.0 g, 7.94 mmol) was dissolved in DMF (25 mL) and cesium carbonate (12.9 g, 39.7 mmol) was added. The mixture was cooled to 0 C and 2,2,2-trifluoroethyl methanesulfonate (2.4 mL, 19.8 mmol) was gradually added. The mixture was warmed to room temperature and stirred for 16 h. Water was added and the mixture was extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (3×10 mL) and concentrated under vacuum. The residue was purified by FCC, eluting with hexane followed by 0.5% MeOH in DCM to afford the title compound as a yellow oil (0.312 g, 19%). Method D HPLC-MS: MH+ requires m/z=209 Found: m/z=209, Rt=2.08 min (98%).

Workup

  1. additionwas gradually added
  2. extractionthe mixture was extracted with EtOAc (3×25 mL)
  3. washThe combined organic extracts were washed with brine (3×10 mL)
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by FCC
  6. washeluting with hexane

Sources & evidence

ORD record
ord-6a1c8410a44f4798b6da0223f45fa1ec
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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