Réaction #84056

Équation de réaction

DMF

2-chloro-6-methoxy-3-methylquinoline

4-(methoxycarbonyl)phenylboronic acid

→

methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate

Rendement 25.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc (25 mL×2)
2. 2
   LavageThe organics were washed with brine (50 mL)
3. 3
   Séchagedried over sodium sulfate
4. 4
   Concentrationconcentrated
5. 5
   Autreto yield 250 mg of crude material
6. 6
   AutreThe crude was purified via column chromatography with a gradient of 5% EtOAc in hexanes to 80% EtOAc in hexanes

Mode opératoire

To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, 0.482 mmol), 4-(methoxycarbonyl)phenylboronic acid (184 mg, 1.02 mmol), TEA (0.35 mL, 2.41 mmol), and PdCl2(dppf) (35 mg, 0.048 mmol) was added 2 mL of DMF under argon. The mixture was then stirred for 2.5 h at 120° C. in a microwave reactor. The crude mixture was then diluted with water (25 mL) and extracted with EtOAc (25 mL×2). The organics were washed with brine (50 mL), dried over sodium sulfate, and concentrated to yield 250 mg of crude material. The crude was purified via column chromatography with a gradient of 5% EtOAc in hexanes to 80% EtOAc in hexanes to yield 37 mg (25% yield) of methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate.

Source