6-BROMO-2,2'-BIPYRIDINE

1.5 g (6.33 mmol) of 2, 6-dibromopyridine, 3.48 g (9.48 mmol) of Intermediate 139-(1), and0.15 g (0.06 mmol) of Pd(PPh3)4 were dissolved in 15 mL of toluene in a 2-necked round-bottom flask, and stirred at about 80° C. for about 24 hours. After evaporation under reduced pressure to remove the solvent, the resulting residue was dissolved in dichloromethane, followed by extraction with 6M HC1. The aqueous layer was separated and collected, and ammonia water was added thereto, followed by extraction with dichloromethane. The resulting organic layer was separated and then dried with anhydrous MgS04, followed by evaporation under reduced pressure to remove the solvent, by drying, and by separation with column chromatography (hexane: ethyl acetate=5:l by v/v) to obtain 0.9 g of Intermediate 139-(2) as white solid (Yield: 61percent).2, 6-Dibromopyridine (19.5 g), 2-pyridylzinc bromide (150 ml), tetrahydrofuran (90 ml), and tetrakis(triphenylphosphine)palladium(0) (4.33 g) were added to a nitrogen-substituted reaction vessel. The mixture was cooled, and stirred at 0°C for 2 hours, and then at room temperature for 3 hours. The reaction mixture was added to a 10percent disodium dihydrogen ethylenediamine tetraacetate aqueous solution, and stirred for 6 hours. The organic layer was collected by separation after adding chloroform (300 ml) . The organic layer was dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was purified by column chromatography (support: silica gel, eluent: toluene) to obtain a white powder of 6-bromo-2, 2'-bipyridine (11.1 g; yield 63percent).General procedure: Into a 25 mL round-bottomed flask were added Pd(PPhTo a solution of 2, 6-dibromopyridine (474 mg, 2 mmol) in tetrahydrofuran (5ml) was added Pd(PPh3)4 (23 mg, 0.02 mmol) under argon, and then a solution of pyridin-2-ylzinc(II) bromide ( 0.5M in tetrahydrofuan, 4.4 ml, 2.2 mmol). The mixture was stirred at 25 °C over a weekend, and then diluted with 150 ml ethyl acetate. The solution was washed with saturated ammonium chloride (20 ml x5) and brine. The organic phase was dried over Na2S04, filtered, and the solvents were removed under vacuum. The product was purified by ISCO chromatography (10-30percent Ethyl acetate in hexanes) to afford the title compound as a white solid (154 mg, 33percent). Calculated for C10H7BrN2, 233.98/235.98; MS (ESI) (m/z) observed 235/237 (M + 1)

Molecular Weight:235.08
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:233.97926
Monoisotopic Mass:233.97926
Topological Polar Surface Area:25.8
Heavy Atom Count:13
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes