Reaction #84099

Reaction equation

2-chloro-6-methoxyquinoline

2-amino-4-(methoxycarbonyl)phenylboronic acid

K2CO3

→

product

Yield 19.0%

methyl 3-amino-4-(6-methoxyquinolin-2-yl)benzoate

Yield 19.0%

Solvents

ethylene glycol monomethyl ether H2O

Conditions

Workup

1. 1
   ExtractionAfter aqueous workup with EtOAc extraction
2. 2
   Otherthe resulting crude product was purified by silica gel column (PE/EtOAc=15/1 to 3/1)

Procedure

To a mixture of compound 2-chloro-6-methoxyquinoline (1.70 g, 8.78 mmol), 2-amino-4-(methoxycarbonyl)phenylboronic acid (2.05 g, 10.5 mmol), and K2CO3 (2.43 g, 17.6 mmol) in ethylene glycol monomethyl ether/H2O (35 mL/5 mL) was added Pd(dppf)Cl2 (158 mg, 0.193 mmol) under N2 atmosphere. Then the mixture was heated to 80° C. for 3 hours. After aqueous workup with EtOAc extraction, the resulting crude product was purified by silica gel column (PE/EtOAc=15/1 to 3/1) to give the product (500 mg, yield 19%) as a yellow solid.

Source