Sodium Carbonate → 3-(2-Chloro-5-nitrophenyl)pyridine

A mixture of 3-bromo-4-chloronitrobenzene (5.17 g, 21.9 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (4.27 g, 26.2 mmol) in ethanol (30 ml) and toluene (30 ml) together with 2 N Na2CO3 solution (13.9 ml) was degassed with a stream of nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.26 mmol) was added and the reaction was heated at reflux for over 24 h. The mixture was concentrated under reduced pressure to remove the organic solvents and water (100 ml) was added. This was extracted with ethyl acetate (200 ml) and then washed with brine (75 ml), dried (MgSO4), and concentrated under reduced pressure while dry loading onto silica. The resulting crude residue was purified by column chromatography (silica gel, 50% Et2O/CH2Cl2), to yield the title compound (3.53 g, 69%): 1H NMR (360 MHz, CDCl3) δ 7.42-7.48 (1H, m), 7.70 (1H, d, J 8.7 Hz), 7.81 (1H, dt, J 8.0, 1.8 Hz), 8.17-8.27 (2H, m), 8.68-8.77 (2H, m).

1. customwas degassed with a stream of nitrogen for 10 min
2. temperaturethe reaction was heated
3. temperatureat reflux for over 24 h
4. concentrationThe mixture was concentrated under reduced pressure
5. customto remove the organic solvents and water (100 ml)
6. additionwas added
7. extractionThis was extracted with ethyl acetate (200 ml)
8. washwashed with brine (75 ml)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated under reduced pressure
11. customwhile dry loading onto silica
12. customThe resulting crude residue was purified by column chromatography (silica gel, 50% Et2O/CH2Cl2)

ORD record

ord-5d81ba80b27c4c67a0b4b11fdd25b41e

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936608B2