Analyzing the synthesis route of Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Application In Synthesis of Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate

To a stirring solution of methyl 1 H-pyrazolo[3,4-c]pyridine-5-carboxylate (0.628 g, 3.545 mmol) in DMF (15 mL) was added 4-fluorobenzyl bromide (0.442 mL, 3.545 mmol) followed by potassium carbonate (0.490 g, 3.545 mmol), and the mixture was stirred overnight at room temperature. Saturated sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The crude solid was purified by flash column chromatography (silica gel, 0-20% acetonitrile: chloroform v/v) to provide pure desired methyl 1-(4-fluorobenzyl)-iH-pyrazolo[3,4-c]pyridine-5-carboxylate (0.66 g, 30% yield over three steps) and the undesired methyl 2-(4-fluoro-benzyl)-2H-pyrazolo[3,4-c]pyridine-5- carboxylate (0.73 g, 33% yield) as white solids. Methyl 1-(4-fluorobenzyl)-lH-pyrazolo[3,4- c] pyridine-5-carboxylate: (at)HNMR (CDCI3, 300 MHz) 8 ppm 8.91 (s, 1 H), 8.59 (s, 1 H), 8.22 (s, 1 H), 7.26 (m, 2H), 7.02 (m, 2H), 5.69 (s, 2H), 4.03 (s, 3H). LCMS (API-ES M+H+) 286. Methyl 2-(4- fluoro-benzyl)-2H-pyrazolo [3,4-c]pyridine-5-carboxylate: ‘HNMR (CDCI3, 300 MHz): 8 ppm 9.32 (s, 1 H), 8.51 (s, 1 H), 8.10 (s, 1 H), 7.36 (m, 2H), 7.09 (m, 2H), 5.65 (2H, s), 4.02 (s, 3H). LCMS (API-ES M+H+) 286.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; WO2005/103003; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem