Реакция #68224

Уравнение реакции

N,N-dimethylformamide

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-(trifluoromethanesulfonyl)oxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

sodium carbonate

4-pyridineboronic acid

→

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-4-(pyridin-4-yl)quinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Растворители

water

ethyl acetate

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   workup.ADDITIONwere added
3. 3
   Другоеthe organic layer was separated
4. 4
   Экстракцияthe aqueous layer was extracted with ethyl acetate
5. 5
   Промывкаwashed with aqueous saturated sodium chloride solution
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   Другоеthe solvent was removed under reduced pressure
8. 8
   ДругоеThe residue thus obtained
9. 9
   Другоеwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

Методика

To 2 mL of an N,N-dimethylformamide solution containing 0.14 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-(trifluoromethanesulfonyl)oxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 0.24 mL of 2.0 mol/L aqueous sodium carbonate solution, 12 mg of tetrakis triphenylphosphine palladium and 39 mg of 4-pyridineboronic acid were added, and stirred at 120° C. under nitrogen atmosphere for 80 min. The reaction mixture was cooled to the room temperature, ethyl acetate and water were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1], to give 42 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-4-(pyridin-4-yl)quinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a pale yellow solid.

Источник