Reaction #41344

Reaction equation

5-Iodo-6-methylindazole

p-fluorobenzeneboronic acid

pyridine

p-fluorobenzeneboronic acid

pyridine

→

subtitle compound

Yield 51.1%

1-(4-Fluorophenyl)-5-iodo-6-methylindazole

Yield 51.1%

Solvents

dichloromethane

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered through celite
2. 2
   ConcentrationThe filtrate was concentrated
3. 3
   Otherpurified by column chromatography (SiO2, toluene)

Procedure

5-Iodo-6-methylindazole (1.3 g, 5.0 mmol), p-fluorobenzeneboronic acid (1.4 g, 10 mmol), anhydrous copper(II) acetate (1.4 g, 7.5 mmol) and pyridine (0.80 mL, 10 mmol) were stirred in dichloromethane (30 mL) overnight. Additional portions of p-fluorobenzeneboronic acid (0.47 g, 3.4 mmol), anhydrous copper(II) acetate (0.45 g, 2.5 mmol) and pyridine (0.27 mL, 3.4 mmol) were added. The mixture was filtered through celite after stirring for an additional night. The filtrate was concentrated and purified by column chromatography (SiO2, toluene) to give the subtitle compound (0.90 g, 51%) as a light orange powder.

Source