6-CHLORO-2,2'-BIPYRIDINE

Step 1 2, 6-dichloropyridine 11 (8.88 g, 60.0 mmol) and 2-(tributylstannyl)pyridine (7.36 g, 20.0mmol) were dissolved in toluene (74 ml). To the solution was added tetrakis triphenyl phosphinepalladium (2.31 g, 2.0 mmol) and the mixture was stirred under heat refluxing for 11 hours. The reactant was condensed under reduced pressure and the residue was purified by silica gel chromatography to give quantitatively the desired Compound 12 (3.9 g). 2, 6-dichloropyridine 11 (8.88 g, 60.0 mmol) and 2-(tributylstannyl)pyridine (7.36 g, 20.0 mmol) were dissolved in toluene (74 ml). To the solution was added tetrakis triphenyl phosphinepalladium (2.31 g, 2.0 mmol) and the mixture was stirred under heat refluxing for 11 hours. The reactant was condensed under reduced pressure and the residue was purified by silica gel chromatography to give quantitatively the desired Compound 12 (3.9 g) 1H-NMR (DMSO-d6) ' ppm: 7.50-7.53 (m, 1H), 7.59 (d, 1H, J=8.0 Hz), 7.93-8.05 (m, 2H), 8.30 (d, 1H, J=8.0 Hz), 8.38 (d, 1H, J=8.0 Hz), 8.72 (d, 1H, J=4.4 Hz).A 9.8 mL phosphoryl chloride solution was added into a mixture of MBPO (0.99 g, 5.32 mmol) and phosphorus pentachloride (0.93 g, 4.46 mmol). The brown mixture was refluxed for 1 day and became a deep brown color. The unreacted phosphorylchloride was removed and then put into an ice bath. Then 100 mL of ice water was added and the precipitate was filtered out. The solution was slowly added intoammonium hydroxide until the pH reached 7. The white precipitate was generated and then collected and recrystallized by dichloromethane in a 76 percent yield. 1H NMR (300 MHz, CDCl3) d (ppm) 8.66 (d, 1H, J = 2.3 Hz, Cl-Bipy-H), 8.39(d, 1H, J = 4.0 Hz, Cl-Bipy-H), 8.34 (d, 1H, J = 3.8 Hz, Bipy-H), 7.82 (t, 1H, J = 3.8 Hz, Bipy-H), 7.77 (t, 1H, J = 3.8 Hz, Bipy-H), 7.35 (d, 1H, J = 3.8 Hz, Bipy-H), 7.31 (t, 1H, J = 7.7 Hz, 1H, Cl-Bipy-H).

Molecular Weight:190.63
XLogP3:2.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:190.0297759
Monoisotopic Mass:190.0297759
Topological Polar Surface Area:25.8
Heavy Atom Count:13
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes