Cesium carbonate → Methyl 4-((1-(4-(5-chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate

Temperatur

60 °C

A reaction mixture of methyl 4-((4,4,4-trifluoro-1-(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)amino)benzoate (7.85 g) obtained in Example 1, step F, 5-chloro-2-iodopyrimidine (4.35 g), tris(dibenzylideneacetone)dipalladium (0.753 g), 2,6-dimethoxy-2′-(dicyclohexylphosphino)biphenyl (1.35 g), cesium carbonate (16.08 g), dimethylformamide (65.8 mL) and water (16.5 ml) was stirred at 60° C. for 24 hr under a nitrogen atmosphere. The reaction mixture was added to saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) and washed with diethyl ether to give the title compound (4.61 g).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe extract was washed with water and saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
6. washwashed with diethyl ether

ORD-Eintrag

ord-849b768d54b14d16bb20768b42f6484e

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09073864B2