Potassium Phosphate, Tribasic → 3-bromo-5-(2-chloro-4-fluorophenyl)-1-methyl-1H-pyrazole

Temperatur

90 °C

A mixture of 3,5-dibromo-1-methyl-1H-pyrazole (i.e. the product of Step B) (2.00 g, 8.33 mmol) in toluene (40 mL) was sparged with a stream of argon for 45 minutes, and then 2-chloro-4-fluorophenylboronic acid (1.59 g, 9.11 mmol), potassium phosphate tribasic (5.30 g, 25.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.48 g, 0.41 mmol) were added. The reaction mixture was heated at 90° C. for 3 h, and then cooled to room temperature and diluted with ethyl acetate (250 mL). The mixture was washed with water (25 mL) and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified by silica gel chromatography (5 to 40% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a white solid (620 mg).

1. customwas sparged with a stream of argon for 45 minutes
2. temperaturecooled to room temperature
3. washThe mixture was washed with water (25 mL) and saturated aqueous sodium chloride solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe resulting material was purified by silica gel chromatography (5 to 40% gradient of ethyl acetate in hexanes as eluant)

ORD-Eintrag

ord-8624a151838f4200b05e2ca0b859e5e5

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08754115B2