Synthetic Route of 5453-67-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 5453-67-8 as follows.
Step 1: Preparation of methyl 6-formylpyridine-2-carboxylate (I-33a) A suspension of dimethylpyridine-2,6-dicarboxylate (1.0 g, 5.12 mmol) in methanol (8 mL) and THF (3 mL) was heated at 75 C. until the solid was dissolved. NaBH4 (184 mg, 4.87 mmol) was then added portion-wise. The mixture was stirred at 70 C. for 1 h. The mixture was cooled to room temperature and 10% citric acid (1.6 mL) was added. The solution was filtered and the filtrate was evaporated to dryness, taken up in dichloromethane, dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by silica gel chromatography, eluting with 0-100% EtOAc in isohexane, to provide a colourless oil which was then dissolved in toluene (20 mL) and chloroform (20 mL). MnO2 (194 mg, 22.2 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was filtered through a pad of fluorosil, eluting with chloroform (30 mL) and the solvent was removed in vacuo to provide the title compound (249 mg, 29%) as white solid. 1H NMR (400 MHz, CDCl3): delta 10.20 (s, 1H), 8.37 (dd, J=1.2, 7.6 Hz, 1H), 8.17 (dd, J=1.2, 7.6 Hz, 1H), 8.08-8.04 (m, 1H), 4.07 (s, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5453-67-8, its application will become more common.
Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; ARMANI, Elisabetta; GHIDINI, Eleonora; BAKER-GLENN, Charles; VAN DE POEL, Herve; WHITTAKER, Ben; US2015/158858; (2015); A1;,
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