2,2'-BIPYRIDINE-5-CARBOXYLIC ACID

2-Chloro-5-methoxycarbonylpyridine (1.3 g, 7.6 mmol) was dissolved in 20 ml of m-xylene and PdCl 2 (PPh 3) 2 (0.27 g, 0.04 mmol) and 2-trimethyltin pyridine (2. 1 g, 8.6 mmol), and the mixture was heated under reflux for 20 hours. After standing to cool it was diluted with ether and filtered through neutral alumina. The filtrate was washed several times with water and dried with anhydrous sodium sulfate. After evaporation of the solvent, purification by silica gel column chromatography gave 1.13 g of compound 10 as a white solid. Yield 70percent. Subsequently, the compound 10 (1.13 g, 5.3 mmol) thus obtained was suspended in 120 ml of ethanol / water at 1: 120, and a solution prepared by dissolving KOH (0.35 g, 6.3 mmol) in 2 ml of water was added, And the mixture was stirred for 3 hours. Thereafter, the ethanol was distilled off by concentration, and 1 mol / L hydrochloric acid was added until neutral. The obtained suspension was extracted three times with chloroform, the extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off. The crude product was purified by silica gel column chromatography to obtain 0.8 g of Compound 11 as a pale yellow solid. Yield 75percent.Step B 2-(Pyrid-2-yl)-5-pyridine carboxylic acid A mixture of 2-trifluoromethanesulfonyloxy-5-pyridine-carboxylic acid (0.442 g, 1.72 mmol), 2-pyridylboronic acid (1.57 g, 12.79 mmol), barium hydroxide (0.813 mg, 2.58 mmol), DME (8 mL) and water (1.5 mL) is purged with dry argon. Tetrakis(triphenylphosphine) palladium(0) (99.0 mg, 0.086 mmol) is added, and the resultant solution is stirred at 80 C. for 4 hours. The solvents are evaporated in vacuo, and the residue is partitioned between EtOAc and water. The aqueous extract is separated, and extracted with EtOAc. The organic extracts are combined, washed with sat. aq. NaHCO3 and 5% aq. Na2 S2 O3, dried, (Na2 SO4) and the solvent is evaporated in vacuo. The residue is purified by chromatography to afford the title compound.2-Chloro-5-methoxycarbonylpyridine (1.3 g, 7.6 mmol) was dissolved in 20 ml of m-xylene and PdCl 2 (PPh 3) 2 (0.27 g, 0.04 mmol) and 2-trimethyltin pyridine (2. 1 g, 8.6 mmol), and the mixture was heated under reflux for 20 hours. After standing to cool it was diluted with ether and filtered through neutral alumina. The filtrate was washed several times with water and dried with anhydrous sodium sulfate. After evaporation of the solvent, purification by silica gel column chromatography gave 1.13 g of compound 10 as a white solid. Yield 70%. Subsequently, the compound 10 (1.13 g, 5.3 mmol) thus obtained was suspended in 120 ml of ethanol / water at 1: 120, and a solution prepared by dissolving KOH (0.35 g, 6.3 mmol) in 2 ml of water was added, And the mixture was stirred for 3 hours. Thereafter, the ethanol was distilled off by concentration, and 1 mol / L hydrochloric acid was added until neutral. The obtained suspension was extracted three times with chloroform, the extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off. The crude product was purified by silica gel column chromatography to obtain 0.8 g of Compound 11 as a pale yellow solid. Yield 75%.

Molecular Weight:200.19
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:200.058577502
Monoisotopic Mass:200.058577502
Topological Polar Surface Area:63.1
Heavy Atom Count:15
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes