Reaction #84097

Reaction equation

2-chloro-6-methoxyquinoline

4-(methoxycarbonyl) phenylboronic acid

sodium carbonate

→

product

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

Solvents

1,4-dioxane water

Conditions

Workup

1. 1
   FiltrationThe precipitates were filtered
2. 2
   Washwashed with EtOAc (10 mL), acetone (10 mL) and water (10 mL) separately
3. 3
   Otherdried

Procedure

A mixture of 2-chloro-6-methoxyquinoline (see U.S. 61/391,225 for synthesis) (200 mg, 1.0 mmol), 4-(methoxycarbonyl) phenylboronic acid (205 mg, 1.1 mmol), Pd(dppf)Cl2 (366 mg, 0.5 mmol) and sodium carbonate (212 mg, 2.0 mmol) in 1,4-dioxane/water (3 mL/0.6 mL) was heated to 120° C. by microwave for 1 h. The precipitates were filtered; washed with EtOAc (10 mL), acetone (10 mL) and water (10 mL) separately; dried to give the product as a black solid. (120 mg, 40.9%).

Source