Potassium Carbonate → HCID 66612439, Verbindung

5-Bromo-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole (i.e. the product of Step B) (0.20 g, 0.66 mmol), palladium(II) acetate (15 mg, 0.066 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (76 mg, 0.13 mmol) and powdered potassium carbonate (1.8 g, 13 mmol) were combined in anhydrous 1,4-dioxane (3 mL), and the mixture was sparged with a subsurface stream of N2 gas for 10 min. 2,6-Difluoro-4-methoxyaniline (0.22 g, 1.3 mmol) was added in one portion, and the reaction mixture was heated at reflux for 22 h. The reaction mixture was filtered through Celite® diatomaceous filter aid, and the filter pad was washed with ethyl acetate (20 mL). The filtrate was washed with water (10 mL) and brine (10 mL), dried over MgSO4, and concentrated to leave a semisolid residue. This residue was purified by column chromatography through 5 g of silica gel eluted with a gradient of hexanes/ethyl acetate (20:1 to 1:3) to give the title compound as a light-brown solid (48 mg).

1. customthe mixture was sparged with a subsurface stream of N2 gas for 10 min
2. temperaturethe reaction mixture was heated
3. temperatureat reflux for 22 h
4. filtrationThe reaction mixture was filtered through Celite® diatomaceous filter aid
5. washthe filter pad was washed with ethyl acetate (20 mL)
6. washThe filtrate was washed with water (10 mL) and brine (10 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customto leave a semisolid residue
10. customThis residue was purified by column chromatography through 5 g of silica gel
11. washeluted with a gradient of hexanes/ethyl acetate (20:1 to 1:3)

ORD-Eintrag

ord-6c76f56e35e34260a5ae690145c13f4a

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09107412B2