반응 #41922

반응 방정식

methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

CHCl3

X-Phos

morpholine

sodium tert-butoxide

→

2-(4-Hydroxy-1-methyl-7-morpholino-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid

수율 18.4%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도the suspension was cooled to 23° C.
2. 2
   여과filtered through celite (
3. 3
   세척extensively washing with methanol), the filtrate
4. 4
   농축concentrated in vacuo
5. 5
   기타purified by silica gel chromatography after adsorption onto silica (eluant: 10% methanol/dichloromethane+1% AcOH)

실험 절차

A solution of methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (100 mg, 271 μmol), Pd2 dba3.CHCl3 (28 mg, 27 μmol), X-Phos (26 mg, 54 μmol) and morpholine (71 μl, 813 μmol) in 1,4-dioxane (3 ml) was treated with sodium tert-butoxide (104 mg, 1084 μmol). The reaction was stirred at 80° C. in a sealed tube. After 24 hours, the suspension was cooled to 23° C., filtered through celite (extensively washing with methanol), the filtrate concentrated in vacuo and purified by silica gel chromatography after adsorption onto silica (eluant: 10% methanol/dichloromethane+1% AcOH), affording 18 mg (18%) of 2-(4-Hydroxy-1-methyl-7-morpholino-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid as a greenish-white solid.

출처