Potassium Phosphate, Tribasic → 5-Cyclopropylpyridin-2-amine

Temperature

80 °C

To a mixture of 5-bromopyridin-2-amine (5.0 g) in a mixed solvent of toluene (100 mL) and water (5 mL) were added cyclopropylboronic acid (4.59 g), tricyclohexyl phosphine (1.62 g), palladium(II) acetate (0.649 g) and tripotassium phosphate (21.5 g) at room temperature. The mixture was stirred overnight at 80° C. under argon atmosphere. The reaction mixture was allowed to be cooled to room temperature, and the insoluble substance was removed by filtration. To the filtrate was added ethyl acetate, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.33 g).

1. temperatureto be cooled to room temperature
2. customthe insoluble substance was removed by filtration
3. additionTo the filtrate was added ethyl acetate
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with water and saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

ORD record

ord-b47c7f36c3e14bfbb29629ce2e45315d

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296746B2