6-Phenylnicotinic acid

General procedure: Under an argon atmosphere, compound (16, 17, 18) (1 equiv.), boronic acid (1.2 equiv.) and Pd[P(CTo a stirred solution of compound A (3 g, 16.16 mmol, 1 eq) in a mixture of dioxane and water (150 mL, 4: 1) mixture were added compound B (3 g, 24.2 mmol, 1.5 eq) and sodium carbonate (8.6 g, 80.8 mmol, 5 eq) and the mixture was degassed with argon for 30 minutes. Pd(PhStep C 2-Phenyl-5-carboxypyridine A suspension of 2-phenyl-5-methyl pyridine (1.03 g, 6.09 mmol) and potassium permanganate (2.89 g, 18.3 mmol), in water (25 mL) was heated at reflux for 2 hours. The reaction was allowed to cool to ambient temperature and filtered through celite to remove the solids. Acetic acid (1 mL) was added to the colourless filtrate and the product was collected as a white solid by filtration. 1 H NMR (CD3 OD, 400 MHz) delta 9.18(1H, s), 8.41(1H, dd, 2.2 and 8.2 Hz), 8.08-8.02(2H, m), 7.97(1H, dd, J=8.2 and 0.7 Hz) and 7.56-7.46(3H, m) ppm.b 6-phenyl-3-pyridinecarboxylic acid A mixture of the compound of Preparation 4(a) (0.4 g, 2.4 mmol) and water (25 mL) was heated to 90 C. and treated with a solution of potassium permanganate (1.58 g, 10 mmol) in a mixture of water (25 mL) and pyridine (25 ml) added slowly. After the purple color disappeared, additional potassium permanganate (1.58 g) was added and the mixture stirred for 5 h. The hot mixture was filtered, the filter cake was washed with water, and the filtrate was concentrated in vacuo to give a white solid, which was dissolved in water (50 mL) and acidified with 3N hydrochloric acid until no additional precipitate formed. The precipitate was filtered and air-dried to give the title compound. MS(ES) m/e 199.7 [M+H]+.

Molecular Weight:199.20
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:199.063328530
Monoisotopic Mass:199.063328530
Topological Polar Surface Area:50.2
Heavy Atom Count:15
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes