Extracurricular laboratory: Synthetic route of 885500-55-0

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885500-55-0, Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 885500-55-0, Ethyl 4-chloro-1H-pyrrolo[2,3-b]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, Quality Control of Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, blongs to pyridine-derivatives compound. Quality Control of Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

General procedure: 5.1.3 Ethyl 4-(cycloheptylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (5c) A mixture of 4 (112 mg, 0.50 mmol), cycloheptanamine (76 muL, 0.60 mmol), and Et3N (209 muL, 1.5 mmol) in NMP (3.0 mL) was heated in a microwave reactor at 180 C for 1 h. After cooling to room temperature, the reaction mixture was quenched with water, extracted with EtOAc, dried over MgSO4, and evaporated in vacuo. The crude mixture was purified by column chromatography on silica gel (CHCl3/MeOH = 100:0 to 90:10) to give the product (135 mg, 90%). 5.1.4 Ethyl 4-[(cyclohexylmethyl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (5d) Compound 5d was prepared in 62% yield as a white solid by a method similar to that described for 5c. 1H NMR (DMSO-d6) delta 1.01-1.33 (m, 5H), 1.31 (t, J = 7.1 Hz, 3H), 1.61-1.86 (m, 6H), 3.52 (t, J = 6.1 Hz, 2H), 4.26 (q, J = 7.1 Hz, 2H), 6.66 (d, J = 3.6 Hz, 1H), 7.15 (d, J = 3.6 Hz, 1H), 8.53 (s, 1H), 8.81 (t, J = 5.4 Hz, 1H), 11.67 (br s, 1H); MS (ESI) m/z 302 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885500-55-0, Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Yamagishi, Hiroaki; Shirakami, Shohei; Nakajima, Yutaka; Tanaka, Akira; Takahashi, Fumie; Hamaguchi, Hisao; Hatanaka, Keiko; Moritomo, Ayako; Inami, Masamichi; Higashi, Yasuyuki; Inoue, Takayuki; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4846 – 4859;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem