Methyl 4-amino-3-chloro-5-fluoro-6-vinylpyridine-2-carboxylate → Methyl 4-amino-3-chloro-6-ethyl-5-fluoropyridine-2-carboxylate

HRID 2113414Notes

Reaction equation

HRID 2113414 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH:9]=[CH2:10])[N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[Cl:15]>C(O)C.[Pd]>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH3:10])[N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[Cl:15]

Participants

4

Reactant 1

HCID 67026737Methyl 4-amino-3-chloro-5-fluoro-6-vinylpyridine-2-carboxylate

Product 1

HCID 67026614Methyl 4-amino-3-chloro-6-ethyl-5-fluoropyridine-2-carboxylateYield 76.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl 4-amino-3-chloro-5-fluoro-6-vinylpyridine-2-carboxylate (3.00 g, 13.0 mmol) and 10% Pd/C (0.30 g) in ethanol (200 mL) was stirred under an atmosphere of hydrogen at 20 psi using a Parr apparatus for 1 hour. The mixture was filtered through celite, concentrated and the residue purified by column chromatography (50% ethyl acetate in hexane) to provide methyl 4-amino-3-chloro-6-ethyl-5-fluoropyridine-2-carboxylate (2.35 g, 10.0 mmol), mp 109-110° C.

Workup

  1. customfor 1 hour
  2. filtrationThe mixture was filtered through celite,
  3. concentrationconcentrated
  4. customthe residue purified by column chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-900188240579460ab8711a25869684eb
Source dataset
uspto-grants-2008_10
Patent number
US07432227B2

Reaction notes

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