Methyl 2-(difluoromethyl)pyridine-4-carboxylate → HCID 59536564, compound

HRID 1963247Notes

Reaction equation

HRID 1963247 reaction equation
[F:1][CH:2]([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([O:8][CH3:9])=[O:7]>C(O)(=O)C.[Pt](=O)=O>[F:13][CH:2]([F:1])[CH:3]1[CH2:4][CH:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:10][CH2:11][NH:12]1

Participants

4

Reactant 1

HCID 59536559Methyl 2-(difluoromethyl)pyridine-4-carboxylate

Product 1

HCID 59536564HCID 59536564, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Methyl 2-(difluoromethyl)isonicotinate (2.4 g, 12.82 mmol) was dissolved in acetic acid (40 mL). Platinum(IV) oxide (0.291 g, 1.28 mmol) was added and the mixture was hydrogenated at 5 bar and room temperature for 7 h in a Büchi hydrogenation apparatus. The catalyst was removed by filtration, fresh platinum(IV) oxide (210 mg, 0.92 mmol) was added and the hydrogenation was continued at 5 bar and room temperature for 6 h. The catalyst was removed by filtration and the solvent evaporated. The residue was taken up in DCM and the organic phase was washed with satd NaHCO3. The aqueous phase was extracted with DCM and the combined organic phases were filtered through a phase separator and evaporated. Methyl 2-(difluoromethyl)piperidine-4-carboxylate (1.85 g, 75%) was isolated. MS m/z 194 (M+H)+

Workup

  1. additionwas added
  2. waitthe hydrogenation was continued at 5 bar and room temperature for 6 h
  3. customThe catalyst was removed by filtration
  4. customthe solvent evaporated
  5. washthe organic phase was washed with satd NaHCO3
  6. extractionThe aqueous phase was extracted with DCM
  7. filtrationthe combined organic phases were filtered through a phase separator
  8. customevaporated

Sources & evidence

ORD record
ord-90e6e8d97445495e90496b094172a0ce
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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