Toluene → Ethyl 2-(4-(2-bromopyridin-4-yl)phenyl)acetate

Temperature

80 °C

To a sealed tube were added 2-bromo-4-iodopyridine 203-1 (568 mg, 2.0 mmol), ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate 203-2 (580 mg, 2.0 mmol), Pd(PPh3)4 (116 mg, 0.1 mmol), Na2CO3 (636 mg, 6.0 mmol), toluene (4 mL), H2O (4 mL) and ethanol (1 mL). The reaction mixture was bubbled with nitrogen for 2 minutes and stirred at 80° C. for 10 hours. After cooling to room temperature, the solvents were evaporated and the residue was redissolved in water (5 ml) and extracted with ethyl acetate (5 mL×3). The combined organic phases were dried over Na2SO4, and concentrated. The residue was purified by silica gel flash chromatography and eluted with 15% ethyl acetate in hexane to give ethyl 2-(4-(2-bromopyridin-4-yl)phenyl)acetate 203-3. MS m/z 320.1 (M+1).

1. customThe reaction mixture was bubbled with nitrogen for 2 minutes
2. temperatureAfter cooling to room temperature
3. customthe solvents were evaporated
4. dissolutionthe residue was redissolved in water (5 ml)
5. extractionextracted with ethyl acetate (5 mL×3)
6. dry with materialThe combined organic phases were dried over Na2SO4
7. concentrationconcentrated
8. customThe residue was purified by silica gel flash chromatography
9. washeluted with 15% ethyl acetate in hexane

ORD record

ord-15f5007a28e84ae48049e0a23dc1508a

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546396B2