The origin of a common compound about 866546-07-8

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Synthetic Route of 866546-07-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 866546-07-8, name is 5-Chloro-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

To 5-chloro-lH-pyrrolo[2,3-]rhoyridine (10.0 g, 65.6 mmol) in EtOAc (70 mL) at 0 C was added dropwise over 15 h a solution of m-chloroperbenzoic acid (57%, 17.9 g,104 mmol) in EtOAc (80 mL). The reaction mixture was stirred for 20 h at RT. Then, the mixture was cooled to -40C and the solids were filtered off and rinsed with cold EtOAc. The solid was taken up in water (70 mL) and treated dropwise with 30% aq. K2CO3 until pEta was 11. The solution was warmed for 30 min, cooled to 0 0C, filtered and dried in vacuo. Analysis (NMR) indicated the presence of m- chloroperbenzoic acid. The solid was taken up in 10% MeOH in DCM and washed with EPO 30% aq. K2CO3 until all m-chlorobenzoic acid was removed. The organic layer was dried over Na2SO4, filtered and concentrated to provide 2.61 g (24% yield) of 5-chloro-lH- pyrrolo[2,3-b]pyridine-iV-oxide (C). The combined mother liquors were concentrated. Flash chromatography (5% MeOEta- DCM) provided and additional 1.49 g (13% yield) contaminated with -10 % of the benzoic acid. LC/MS (M + H+) 168.76.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/127587; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem