Reacción #2254184

Ecuación de reacción

Pyridine-4-boronic acid

3-(5-bromo-4-methyl-thiophen-2-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

K2CO3

→

4-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-pyridine

Rendimiento 40.2%

Disolventes

THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction is quenched with water
2. 2
   Extracciónextracted three times with ethyl acetate
3. 3
   Secadodried over MgSO4
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe crude product is purified on a semi-preparative HPLC

Procedimiento

, Pyridine-4-boronic acid (30 mg) is added to a solution of 3-(5-bromo-4-methyl-thiophen-2-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (100 mg), K2CO3 (90 mg) and Pd(PPh3)4 (20 mg) in a mixture of THF and water (0.4 ml, 9:1). After 22 hours at 70° C., the reaction is quenched with water and extracted three times with ethyl acetate. The organic phases are combined, dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 4-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-pyridine (40 mg) as a colorless oil. MS (HPLC/MS): 457 (MH+). Retention time: 5.20 min.

Fuente