Reacción #73881

Ecuación de reacción

1-(4′-{3-Methyl-4-[6-bromo-pyridin-2-ylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

sodium bicarbonate

DME

o-tolylboronic acid

→

title compound

1-(4′-{3-Methyl-4-[6-(2-methyl-phenyl)-pyridin-2-ylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

Disolventes

EtOAc

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was cooled to room temperature
2. 2
   Extracciónextracted with H2O (2×10 mL)
3. 3
   SecadoThe organic layer was dried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   Otrothe crude residue was purified on reverse-phase preparative HPLC

Procedimiento

1-(4′-{3-Methyl-4-[6-bromo-pyridin-2-ylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester (0.050 g, 0.09 mmol), o-tolylboronic acid (0.016 g, 0.12 mmol), sodium bicarbonate (0.040 g, 0.48 mmol), and bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.007 g, 0.009 mmol) were combined in 3:1 DME:H2O (2 mL) and warmed with stirring to 70° C. After 3 hrs, the mixture was cooled to room temperature diluted with EtOAc (30 mL) and extracted with H2O (2×10 mL). The organic layer was dried over MgSO4, filtered and concentrated, and the crude residue was purified on reverse-phase preparative HPLC to afford the title compound.

Fuente