2-HYDROXY-4-PYRIDINECARBOXALDEHYDE

5 - { [2-Diftuoromethoxy)pyridine-4-yl] methyl } - 8 - [(IS, 25)-2-hydroxycyclohexyl] -1, 8- phenanthrolin-7(8H)-one; Synthesis of [2-(difluoromethoxy)pyridine-4-yl]methanol.; To a solution of 2-oxo-l52-dihydropyridine-4-carbaldehyde (1.72 g, 11.3 mmol) in 25 mL of acetonitrile was added sodium chlorodifluoroacetate (0.925 g, 7.51 mmol). The reaction was heated to reflux under an atmosphere of nitrogen for 15 h, and then DMF (3 mL) was added. The mixture was heated to 100 C for 3 d, cooled to it, and diluted with ethyl acetate. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 3 -(difluoromethoxy)benzaldehyde .To a solution of 2-hydroxyisonicotinaldehyde (1.00 g, 8.12 mmol) in 25 mL of acetontitrile was added sodium chlorodifluoroacetate (1.86 g, 12.2 mmol). The reaction was heated to reflux for 20 h, cooled to rt, and diluted with ethyl acetate. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was redissolved in 20 mL of methanol and placed under an atmosphere of nitrogen. Sodium borohydride (0.307 g, 3.12 mmol) was added in 3 portions, and after 2 h, the reaction was treated with brine and diluted extracted 2x with dichloromethane. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-(difluoromethoxy)pyridine-4- yljmethanol that gave a mass ion (ES+) of 176.1 for [M+H]+.4-[(E)-2-(4-Fluoro-phenyl)-vinyl]-pyridin-2-ol:To a solution of dieihyl-4-fI'iorobenzyl-phosphonatc (515 mg, 2.09 mmol) in THF ( 10.0 mL) was added potassium tert-buloxide (246 mg, 2.09 mmol). After stirring at 20 0C for 1 h, the mixture was treated with 2-hydroxypyridoaIdehyde (246 mg, 2.00 mmol), and allowed to stir for 3 h at 20 0C. The reaction mixture was quenched with water, and the aqueous phase was extracted with DCM, the combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude oil was purified by column chromatography (DCM to 20%methanol in DCM) gave the desired product 4-[(L)-2-(4-fluoro-phenyO-vinyl]-pyridin-2-ol (32.0 mg, 7.5%, 5: 1 transxis) as white crystal. 1H NMR (400 MHz, CDCh) ?: 7.56 (m, 2H), 7.33 (m, I H), 7.26 (m, IH), 7.08 (m, 2H), 6.87 (m, IH), 6.64 (m, IH), 6.54 (m, IH); ESMS m/e: 216 (M+H)+.A mixture of (R)-2-(2-Hydroxy-pyridin-4-yl)-thiazolidine-4-carboxylic acidTo a solution of L-cysteine hydrochloride (402.9 mg, 2.56 mmol) in distilled water (4 mL), potassium acetate (281.7 mg, 2.87 mmol) was added. Once the solids went into solution, methanol (4 mL) was added followed by

Molecular Weight:123.11
XLogP3:-0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:123.032028402
Monoisotopic Mass:123.032028402
Topological Polar Surface Area:46.2
Heavy Atom Count:9
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes