HCID 86667925, compound → HCID 67085815, compound

HRID 1486656Notes

Reaction equation

HRID 1486656 reaction equation
[F:1][C:2]([F:20])([F:19])[CH:3]([C:9]1[CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=1)OS(C)(=O)=O>CO.[Pd]>[F:20][C:2]([F:1])([F:19])[CH2:3][C:9]1[CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=1

Participants

4

Reactant 1

HCID 86667925HCID 86667925, compound

Product 1

HCID 67085815HCID 67085815, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 5-(2,2,2-trifluoro-1-(methylsulfonyloxy)ethyl)picolinate (95 mg, 0.3 mmol) in 5 mL of MeOH was added 10% Pd/C (45 mg). Hydrogenation with 1 atm H2 was carried out at room temperature for 2 h. After the catalyst was removed by filtration, the filtrated was concentrated. The residue was dissolved in DCM and washed with sat. NaHCO3 (aq,), and brine. The solution was dried (MgSO4) and concentrated to give methyl 5-(2,2,2-trifluoroethyl)picolinate that was used without purification.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrated was concentrated
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with sat. NaHCO3 (aq,), and brine
  5. dry with materialThe solution was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef27c47040704e08a364598350a34bde
Source dataset
uspto-grants-2016_08
Patent number
US09428475B2

Reaction notes

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