Cesium carbonate → HCID 86690474, compound

Temperature

150 °C

A mixture of N-[(2-bromopyridin-4-yl)methyl]propan-2-amine (2.00 g), 4-fluorophenylboronic acid (1.34 g), cesium carbonate (4.26 g), tetrakis(triphenylphosphine)palladium (1.01 g), toluene (4.5 mL), ethanol (4.5 mL) and water (3.0 mL) was stirred under irradiation with microwave while heating at 150° C. for 30 min. Saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture, and the resulting mixture was then filtered through Celite and extracted with ethyl acetate. The whole organic phase was collected and dried over magnesium sulfate. After the desiccant was filtered off, the solution was concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=96:4-92:8) and (NH silica gel cartridge, hexane:ethyl acetate=90:10-60:40) to afford the title compound (1.13 g).

1. filtrationthe resulting mixture was then filtered through Celite
2. extractionextracted with ethyl acetate
3. customThe whole organic phase was collected
4. dry with materialdried over magnesium sulfate
5. filtrationAfter the desiccant was filtered off
6. concentrationthe solution was concentrated under reduced pressure
7. customThe resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=96:4-92:8) and (NH silica gel cartridge, hexane:ethyl acetate=90:10-60:40)

ORD record

ord-e92c977e3fae4cef8c68e551f184cff5

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729271B2