With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.69950-65-8, name is Methyl 6-formyl-2-pyridinecarboxylate, molecular formula is C8H7NO3, molecular weight is 165.15, as common compound, the synthetic route is as follows.name: Methyl 6-formyl-2-pyridinecarboxylate
To a solution of 6-chloro-2-(2-chlorophenyl)pyrazolo[1,5-a]pyridine (83, 173 mg, 0.657 mmol) and ethyl 2-formylthiazole-4-carboxylate (130 mg, 0.79 mmol) in dichloromethane (6.5 mL) were added triethylsilane (0.525 mL, 3.29 mmol) and trifluoroacetic acid (0.252 mL, 3.29 mmol) at room temperature. After stirring at 80 C for 9 h, additional triethylsilane (0.525 mL, 3.29 mmol) and trifluoroacetic acid (0252 mL, 3.29 mmol) were added to the mixture. After stirring at 80 C for 48 h, saturated aq. sodium bicarbonate was added to the mixture. The mixture was then extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt = 5:1) to give the title compound 94 as a dark brown amorphous material (65.0 mg, 25%). 1H-NMR (400 MHz, CDCl3) delta 4.01 (3H, s), 4.29 (2H, s), 7.06 (2H, dd, J = 9.7, 1.2 Hz), 7.33-7.36 (2H, m), 7.41 (1H, td, J = 6.7, 2.4 Hz), 7.45-7.49 (2H, m), 7.62 (1H, t, J = 7.6 Hz), 7.91 (1H, d, J = 7.3 Hz), 8.50 (1H, d, J = 1.2 Hz). IR (ATR) nmax 3062, 2950, 1722, 1587, 1535, 1451, 1318 cm-1. HRMS (ESI) calcd for C21H16Cl2N3O2 (M+H) 412.0620, found 412.0616.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, and friends who are interested can also refer to it.
Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Saito, Yoshifumi; Watanabe, Hiroyuki; Kondo, Tatsuhiro; Kondo, Atsushi; Kawamura, Naohiro; Tatani, Kazuya; Kohno, Yasushi; Tanaka, Nobuyuki; Seto, Shigeki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 17; (2017); p. 4044 – 4050;,
Pyridine – Wikipedia,
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