Réaction #42566

Équation de réaction

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

thiazole

n-butyl lithium

→

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

Rendement 99.1%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   TempératureThe mixture was then heated at 80° C. for 2 h, at which time it
3. 3
   Températureto cool
4. 4
   Autrepartitioned between ethyl acetate and water
5. 5
   LavageThe organic layers were washed with brine
6. 6
   Séchagedried (magnesium sulfate)
7. 7
   Concentrationconcentrated
8. 8
   AutreThe residue was chromatographed on silica gel

Mode opératoire

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.

Source