Methyl 1,2-dihydro-2-oxopyridine-4-carboxylate

A. Methyl 2-oxo-l, 2-dihydropyridine-4-carboxylate[0095] To MeOH (80 mL) at 0Example 170 1- (2-Cyclopropyl-3-methylimidazo [1, 2-a] pyridin-6-yl) -4- ( (4- fluorophenoxy) methyl) pyridin-2 ( 1H) -one A) Methyl 2-oxo-l, 2-dihydropyridine-4-carboxylate To a stirred solution of 2-hydroxypyridine-4-carboxylic acid (5.0 g) in MeOH (50 ml) was added acetyl chloride (26 ml) dropwise at 0°C over 15 min. The reaction mixture was slowly warmed to room temperature, and stirred for 20 h. The reaction mixture was concentrated in vacuo, and diluted with EtOAc and water. The organic layer was washed with saturated NaHCC>3 solution, concentrated in vacuo, and purified by column chromatography (MeOH/DCM) to afford the title compound (3.5 g) as an off-white solid. MS (ESI+) : [M+H]+ 154.0.Methyl 2-(acetyloxy)-4-pyridinecarboxylate (5.0 g) and methanol (50 ml_) were heated at 73Methyl 2-oxo-1, 2-dihydropyridine-4-carboxylate (1.730 g, 11.297 mmol) was dissolved in N, N-dimethylformamide (30 mL) at 0C, after which hydrogenated sodium (60.00%, 0.678 g, 16.945 mmol) was added into the resulting solution, and stirred at the same temperature for 30 minutes. 2-(bromomethyl)naphthalene (2.498 g, 11.297 mmol) was added into the reaction mixture, and further stirred at room temperature for three hours. Water was poured into the reaction mixture, and an extraction was performed with ethyl acetate. An organic layer was washed with saturated sodium chloride aqueous solution, then dehydrated with anhydrous sodium sulfate, then filtered, and then concentrated under reduced pressure. A concentrate was purified via column chromatography (SiO 2, 12 g cartridge; ethyl acetate/hexane = 0 to 30%), and concentrated to obtain the title compound (2.800 g, 84.5%) in a white solid form.

Molecular Weight:153.14
XLogP3:-0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:153.042593085
Monoisotopic Mass:153.042593085
Topological Polar Surface Area:55.4
Heavy Atom Count:11
Complexity:252
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes