Reaktion #42566

Reaktionsgleichung

methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate

thiazole

n-butyl lithium

→

methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate

Ausbeute 99.1%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturThe mixture was then heated at 80° C. for 2 h, at which time it
3. 3
   Temperaturto cool
4. 4
   Sonstigepartitioned between ethyl acetate and water
5. 5
   WaschenThe organic layers were washed with brine
6. 6
   Trocknendried (magnesium sulfate)
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was chromatographed on silica gel

Vorschrift

To a −78° C. solution of thiazole (1.2 g) in THF (25 mL) was added n-butyl lithium (1.6 M in hexanes, 10 mL). The mixture was stirred for 30 min and then allowed to warm to 0° C. in an ice/water bath. Zinc chloride (1M in ethyl ether, 40 mL) was added and the mixture was stirred for 1 h, at which time methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate (5.1 g) in THF (20 mL) was added, followed by Pd(PPh3)4 (palladium tetrakis triphenylphosphine) (0.68 g). The mixture was then heated at 80° C. for 2 h, at which time it was allowed to cool and partitioned between ethyl acetate and water. The organic layers were washed with brine, dried (magnesium sulfate), and concentrated. The residue was chromatographed on silica gel using ethyl acetate/heptane (50/50) to give 4.5 g of methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate.

Quelle