Oxazole → Methyl 3-{[butyl(methyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate

Temperatur

0 °C

To a −70° C. stirred solution of oxazole (167 mg, 2.4 mmol) in tetrahydrofuran (4 mL) is added n-butyllithium (1.6 M in hexanes, 1.7 mL, 2.7 mmol). After 30 min, zinc chloride (1 M in diethyl ether, 7.3 mL, 7.3 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-{[butyl(methyl)amino]carbonyl)-5-iodobenzoate (864 mg, 2.3 mmol) in anhydrous tetrahydrofuran (3 mL) followed by palladium(0) tetrakis(triphenylphosphine) (112 mg, 0.10 mmol). The reaction mixture is heated at reflux for 1.5 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]+.

1. temperatureThe reaction mixture is heated
2. temperatureat reflux for 1.5 h
3. temperatureThe reaction mixture is cooled
4. washwashed with water, and saturated sodium chloride
5. dry with materialdried (sodium sulfate)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customPurification by flash column chromatography (silica gel, 60% ethyl acetate/hexane)

ORD-Eintrag

ord-6946931479f54928b4f8224bb8d99843

Quelldatensatz

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07176242B2