Reaction #2200596

Reaction equation

methyl 4-amino-3-chloro-5-fluoro-6-vinylpyridine-2-carboxylate

→

methyl 4-amino-3-chloro-6-ethyl-5-fluoropyridine-2-carboxylate

Yield 76.9%

Solvents

ethanol

Conditions

Workup

1. 1
   Otherfor 1 hour
2. 2
   FiltrationThe mixture was filtered through celite,
3. 3
   Concentrationconcentrated
4. 4
   Otherthe residue purified by column chromatography (50% ethyl acetate in hexane)

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.

Source