Reaktion #989729

Reaktionsgleichung

7-bromo-2-methyl-2H-indazole

2,4,6-trimethylphenyl boronic acid

K2HPO4

→

2-methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole

Ausbeute 60.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was partitioned between 350 mL of diethyl ether and 350 ML of water
2. 2
   WaschenThe organic layer was washed with 350 mL of a saturated aqueous NaCl solution
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated to a pale yellow oil

Vorschrift

A mixture of 7-bromo-2-methyl-2H-indazole (6: R=Me; 2.01 g, 9.53 mmol), 2,4,6-trimethylphenyl boronic acid (1.70 g, 10.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.657 g, 0.569 mmol), 70 mL of DMF, and 33 mL of a 2 M aqueous K2HPO4 solution was stirred at 69° C. for 6.5 d. The mixture was partitioned between 350 mL of diethyl ether and 350 ML of water. The organic layer was washed with 350 mL of a saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated to a pale yellow oil. Column chromatography (0→33% EtOAc/hexanes) afforded of impure 2-methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole (5: R=Me, Ar=2,4,6-trimethylphenyl; 1.44 g) as a white solid that was used without further purification.

Quelle