Reacción #164928

Ecuación de reacción

3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzoic acid methyl ester

2-bromo-5 methyl-pyridine

K3PO4

→

3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester

Rendimiento 56.3%

Disolventes

dimethoxy ethylene

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was flushed with N2
2. 2
   TemperaturaThe reaction mixture was cooled
3. 3
   Otrothe residue was purified by column chromatography (EtOAc/hexane=1:3)

Procedimiento

To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130° C. for 30 minutes. The reaction mixture was cooled, solvent wasremoved under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.

Fuente