Reacción #42580

Ecuación de reacción

n-butyllithium

oxazole

methyl 3-{[ethyl(propyl)amino]carbonyl}-5-iodobenzoate

→

title compound

Methyl 3-{[ethyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate

Disolventes

ethyl acetate

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture is heated
2. 2
   Temperaturaat reflux for 2 h
3. 3
   TemperaturaThe reaction mixture is cooled
4. 4
   Lavadowashed with water, and saturated sodium chloride
5. 5
   Secadodried (sodium sulfate)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroPurification by flash column chromatography (silica gel, 60% ethyl acetate/hexane)

Procedimiento

To a −70° C. stirred solution of oxazole (106 mg, 1.5 mmol) in tetrahydrofuran (4 mL) is added n-butyllithium (1.6 M in hexanes, 1.0 mL, 1.7 mmol). After 30 min, zinc chloride (1 M in diethyl ether, 4.6 mL, 4.6 mmol) is added and the reaction mixture is warmed to 0° C. for 1 h. To this mixture is added a solution of methyl 3-{[ethyl(propyl)amino]carbonyl}-5-iodobenzoate (535 mg, 1.45 mmol) in anhydrous tetrahydrofuran (1.8 mL) followed by palladium(0)tetrakis(triphenylphosphine) (120 mg, 0.10 mmol). The reaction mixture is heated at reflux for 2 h. The reaction mixture is cooled, diluted with ethyl acetate, washed with water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 60% ethyl acetate/hexane) provides the title compound. ESI MS m/z 317.1 [M+H]+.

Fuente