Reacción #41921

Ecuación de reacción

ethyl 2-(6-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-6-morpholino-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid

Rendimiento 11.0%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo
2. 2
   Otropurified by silica gel chromatography (eluant: 4% methanol/dichloromethane, followed by/dichloromethane+1% AcOH) and subsequently by RP HPLC (0-100% MeCN/water+1% TFA, 10 min)

Procedimiento

A solution of ethyl 2-(6-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (202 mg, 527 μmol), Pd2 dba3.CHCl3 (55 mg, 53 μmol), X-Phos (50 mg, 105 μmol) and morpholine (115 μl, 1318 μmol) in 1,4-dioxane (3 ml) was treated with sodium tert-butoxide (203 mg, 2109 μmol). The reaction was stirred at 80° C. in a sealed tube. After 21 hours, the solution was adsorbed onto silica gel, concentrated in vacuo and purified by silica gel chromatography (eluant: 4% methanol/dichloromethane, followed by/dichloromethane+1% AcOH) and subsequently by RP HPLC (0-100% MeCN/water+1% TFA, 10 min) affording 21 mg (11%) of 2-(4-hydroxy-1-methyl-6-morpholino-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid as an yellow solid.

Fuente