Ammonium formate → 3-Pyridinecarboxylic acid, 5-fluoro-6-methyl-, methyl ester

HRID 1810981Notes

Reaction equation

HRID 1810981 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH3:11])=[N:6][C:5]=1Cl.C([O-])=O.[NH4+]>[Pd]>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH3:11])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 57516327HCID 57516327, compound

Product 1

HCID 575163283-Pyridinecarboxylic acid, 5-fluoro-6-methyl-, methyl esterYield 61.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask containing 10% Pd/C (0.20 g, 0.19 mmol) and 2-chloro-5-fluoro-6-methyl-nicotinic acid methyl ester (0.410 g, 2.01 mmol) is placed under an atmosphere of Ar. The atmosphere of the vessel is evacuated and refilled with Ar three times. To this is added MeOH (30 mL) followed by ammonium formate (1.0 g, 16 mmol). The mixture is stirred at room temperature for 1 h. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to provide a solid. The material is washed with EtOAc and filtered to remove insoluble material. The filtrate is concentrated under reduced pressure to provide 0.210 g (61.6%) of 5-fluoro-6-methyl-nicotinic acid methyl ester as a solid.

Workup

  1. customThe atmosphere of the vessel is evacuated
  2. additionrefilled with Ar three times
  3. additionTo this is added MeOH (30 mL)
  4. filtrationThe mixture is filtered through a pad of diatomaceous earth
  5. concentrationconcentrated under reduced pressure
  6. customto provide a solid
  7. washThe material is washed with EtOAc
  8. filtrationfiltered
  9. customto remove insoluble material
  10. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3d4461889e34a879fdbece0e5308dae
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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