Reaction #84058

Reaction equation

HCl

DEGME

2-chloro-6-methoxy-3-methylquinoline

4-(1H-tetrazol-5-yl)phenylboronic acid

K2CO3

→

desired product

Yield 84.0%

2-(4-(1H-tetrazol-5-yl)phenyl)-6-methoxy-3-methylquinoline

Yield 84.0%

Solvents

H2O

NaOH

Conditions

Workup

1. 1
   FiltrationThe solids were filtered

Procedure

To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, 0.482 mmol), 4-(1H-tetrazol-5-yl)phenylboronic acid (91.2 mg, 0.482 mmol), K2CO3 (199 mg, 1.45 mmol), and PdCl2(dppf) (17.6 mg, 0.024 mmol) was added 7 mL of DEGME and 3 mL of H2O under argon. The mixture was stirred at 150° C. in a microwave reactor for 1.5 hours. The crude mixture was diluted with 1N NaOH (10 mL) and slowly acidified to a pH of 4.0 using conc. HCl. The solids were filtered to yield 128 mg (84% yield) of desired product.

Source