Reference of 69950-65-8 ,Some common heterocyclic compound, 69950-65-8, molecular formula is C8H7NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a solution of 3-bromo-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridine (18, 550 mg, 1.59 mmol) in THF (4 mL) was added n-butyllithium (0.7 mL, 1.91 mmol, 2.6 mol/L solution in hexane) at -78 C. After stirring at -78 C for 0.5 h, a solution of methyl 6-formylpicolinate (527 mg, 3.19 mmol) in THF (4 mL) was added to the mixture at -78 C. The solution was stirred at room temperature for 1 h, and then the reaction was quenched by the addition of saturated aq. ammonium chloride. The mixture was 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 = 4:1) to give the title compound 23 as a yellow oil (361 mg, 53%). 1H-NMR (400 MHz, CDCl3) delta 0.63 (9H, s), 4.21 (3H, s), 5.53 (1H, d, J = 2.4 Hz), 6.46 (1H, d, J = 2.4 Hz), 6.99 (1H, dd, J = 6.7, 1.8 Hz), 7.06 (1H, dd, J = 9.1, 6.7 Hz), 7.18 (1H, dd, J = 9.1, 1.8 Hz), 7.41-7.44 (2H, m), 7.62 (2H, tt, J = 7.3, 1.2 Hz), 7.86 (1H, t, J = 7.3 Hz), 8.03-8.07 (2H, m), 8.18 (1H, d, J = 7.3 Hz). IR (ATR) nmax 3417, 2953, 2898, 1720, 1586, 1516, 1439, 1356, 1314, 1243, 1138, 1079, 1029, 992, 892, 833, 759, 706, 634, 582, 506, 419 cm-1. MS (ESI) 432 [M+H]+. HRMS (ESI) calcd for C24H26N3O3Si [M+H]+ 432.17434, found 432.17514.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69950-65-8, its application will become more common.
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,
Pyridine | C5H5N – PubChem