تفاعل #85119

معادلة التفاعل

tert-butyl 4-{[2-(4-bromo-5-methoxy-2-oxopyridin-1(2H)-yl)propanoyl]amino}benzoate

2-(5-chloro-2-cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

potassium carbonate

→

tert-Butyl 4-({2-[4-(5-chloro-2-cyclopropylphenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىalready preheated to 110° C
2. 2
   ترشيحThe reaction mixture was filtered through Celite
3. 3
   غسيلthe residue was washed with dioxane
4. 4
   تركيزThe combined filtrates were concentrated under reduced pressure
5. 5
   أخرىThe residue was triturated with water
6. 6
   ترشيحfiltered off
7. 7
   غسيلwashed with water
8. 8
   أخرىdried under reduced pressure
9. 9
   أخرىpurified by flash chromatography (silica gel-50, cyclohexane/ethyl acetate gradient)

الإجراء التجريبي

Under argon (in a flask dried by heating), 125 mg (0.27 mmol) of tert-butyl 4-{[2-(4-bromo-5-methoxy-2-oxopyridin-1(2H)-yl)propanoyl]amino}benzoate (racemate), 92 mg (0.33 mmol, 1.2 eq.) of 2-(5-chloro-2-cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 114 mg (0.82 mmol, 3.0 eq.) of potassium carbonate and 22 mg (0.03 mmol, 0.1 eq.) of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct were suspended in 5.0 ml of dioxane and stirred overnight in an oil bath already preheated to 110° C. The reaction mixture was filtered through Celite and the residue was washed with dioxane. The combined filtrates were concentrated under reduced pressure. The residue was triturated with water, filtered off, washed with water, dried under reduced pressure and purified by flash chromatography (silica gel-50, cyclohexane/ethyl acetate gradient). Yield: 114 mg (79% of theory)

المصدر