Reaction #2122728

Reaction equation

6-chloro-4-(trifluoroacetyl)aminopyridine-3-carboxylic acid ethyl ester

3-(4-methoxybenzyl)amino-6-morpholinopyridine

2,2′-bis (diphenylphosphino)-1,1′-binaphthyl

sodium carbonate

→

title compound

6-[4-methoxybenzyl-(6-morpholinopyridin-3-yl)amino]-4-[(trifluoroacetyl)amino]pyridine-3-carboxylic acid ethyl ester

Solvents

water

toluene

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   TemperatureAfter cooling
3. 3
   Extractionextracted with chloroform
4. 4
   Washthe extract was washed with saturated saline
5. 5
   Dryingdried on anhydrous sodium sulfate
6. 6
   OtherThe solvent was evaporated
7. 7
   Otherthe residue was purified by silica gel thin layer chromatography (hexane:ethyl acetate=1:1)

Procedure

21.8 mg of 6-chloro-4-(trifluoroacetyl)aminopyridine-3-carboxylic acid ethyl ester and 22 mg of 3-(4-methoxybenzyl)amino-6-morpholinopyridine were dissolved in 1 mL of toluene, to which 1.7 mg of palladium (II) acetate, 9.2 mg of 2,2′-bis (diphenylphosphino)-1,1′-binaphthyl and 202 mg of sodium carbonate were added, and stirred overnight at 100° C. After cooling, water was added to the reaction mixture, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (hexane:ethyl acetate=1:1) to obtain 5.7 mg (ylod 14%) of the title compound as a light yellow solid.

Source