Reaktion #995742

Reaktionsgleichung

ethyl 2-(4-hydroxy-1-methyl-2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydroquinoline-3-carboxamido)acetate

4,6-dichloropyrimidine

sodium carbonate

→

Ethyl 2-(6-(6-chloropyrimidin-4-yl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 10 ml reaction
2. 2
   Sonstigethe reaction
3. 3
   SonstigeAfter reaction
4. 4
   Einengenthe reaction mixture was concentrated on a roto-evaporator
5. 5
   Extraktionextracted with EtOAc
6. 6
   Waschenwashed with water and brine (3× ea.)
7. 7
   Trocknenthen dried with MgSO4
8. 8
   Einengenconcentrated on a roto-evaporator
9. 9
   WaschenThe yellow solid was washed with EtOH
10. 10
    Filtrationfiltered
11. 11
    Waschenthe solid was washed with ether

Vorschrift

To a 10 ml reaction vial was charged ethyl 2-(4-hydroxy-1-methyl-2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydroquinoline-3-carboxamido)acetate (200 mg, 465 μmol) in 1,4-dioxane (5 ml), 4,6-dichloropyrimidine (69 mg, 465 μmol), tetrakis(triphenylphosphine) palladium(0) (27 mg, 23 μmol) and sodium carbonate (0.7 ml, 1395 μmol), and the reaction vial was heated to 70° C. After reaction was complete, the reaction mixture was concentrated on a roto-evaporator, extracted with EtOAc, washed with water and brine (3× ea.) then dried with MgSO4 and concentrated on a roto-evaporator. The yellow solid was washed with EtOH and filtered and the solid was washed with ether. Yield=55 mg.

Quelle