Reacción #603732

Ecuación de reacción

Methyl 4-amino-3,6-dichloropicolinate

2-(3-fluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

potassium fluoride

→

title compound

Rendimiento 57.4%

methyl 4-amino-3-chloro-6-(3-fluoro-4-(trifluoromethyl)phenyl)picolinate

Rendimiento 57.4%

Disolventes

acetonitrile water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water
2. 2
   ExtracciónThe aqueous layer was extracted with ethyl acetate
3. 3
   Secadothe combined organic layers were dried over anhydrous sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   Otrodried in vacuum oven
7. 7
   OtroPurification by reverse-phase flash chromatography (0-60, 60, 60-100% acetonitrile/water)

Procedimiento

Methyl 4-amino-3,6-dichloropicolinate (630 mg, 2.85 mmol), 2-(3-fluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.06 g, 3.65 mmol, 1.3 equiv), bis(triphenylphosphine)palladium(II) chloride (209 mg, 0.30 mmol, 0.1 equiv), and potassium fluoride (510 mg, 8.8 mmol, 3 equiv) in acetonitrile/water (8 mL, 3:1) was capped in a 25-mL vial on a Biotage Initiator™ microwave reactor for 20 min at 115° C., with external IR-sensor temperature monitoring from the side of the vessel. The reaction mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude compound was loaded onto a Celite™ cartridge and dried in vacuum oven. Purification by reverse-phase flash chromatography (0-60, 60, 60-100% acetonitrile/water) afforded the title compound as a white solid (0.57 g, 57%).

Fuente