917023-06-4 | Pyridine-derivatives

Smolinski, Michael P. et al. published their research in Journal of Medicinal Chemistry in 2018 | CAS: 917023-06-4

Methyl 2-(5-bromopyridin-2-yl)acetate (cas: 917023-06-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Category: pyridine-derivatives

Discovery of Novel Dual Mechanism of Action Src Signaling and Tubulin Polymerization Inhibitors (KX2-391 and KX2-361) was written by Smolinski, Michael P.;Bu, Yahao;Clements, James;Gelman, Irwin H.;Hegab, Taher;Cutler, David L.;Fang, Jane W. S.;Fetterly, Gerald;Kwan, Rudolf;Barnett, Allen;Lau, Johnson Y. N.;Hangauer, David G.. And the article was included in Journal of Medicinal Chemistry in 2018.Category: pyridine-derivatives This article mentions the following:

The discovery of potent, peptide site directed, tyrosine kinase inhibitors has remained an elusive goal. Herein we describe the discovery of two such clin. candidates that inhibit the tyrosine kinase Src. Compound 1 is a phase 3 clin. trial candidate that is likely to provide a first in class topical treatment for actinic keratosis (AK) with good efficacy and dramatically less toxicity compared to existing standard therapy. Compound 2 is a phase 1 clin. trial candidate that is likely to provide a first in class treatment of malignant glioblastoma and induces 30% long-term complete tumor remission in animal models. The discovery strategy for these compounds iteratively utilized mol. modeling, along with the synthesis and testing of increasingly elaborated proof of concept compounds, until the final clin. candidates were arrived at. This was followed with mechanism of action (MOA) studies that revealed tubulin polymerization inhibition as the second MOA. In the experiment, the researchers used many compounds, for example, Methyl 2-(5-bromopyridin-2-yl)acetate (cas: 917023-06-4Category: pyridine-derivatives).

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Yang, Shao-Qian et al. published their research in Journal of the American Chemical Society in 2021 | CAS: 917023-06-4

Methyl 2-(5-bromopyridin-2-yl)acetate (cas: 917023-06-4) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Related Products of 917023-06-4

Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis was written by Yang, Shao-Qian;Wang, Yi-Fan;Zhao, Wei-Cheng;Lin, Guo-Qiang;He, Zhi-Tao. And the article was included in Journal of the American Chemical Society in 2021.Related Products of 917023-06-4 This article mentions the following:

Herein we describe a protocol for the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes bearing a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A broad scope of conjugated enynes are coupled with various α-fluoroesters in high yields with high diastereoselectivities and generally >99% ee. In addition, the four stereoisomers of the allene products ensure precise access to the corresponding four stereoisomers of the fluorinated hydrofurans via a novel stereodivergent axial-to-central chirality transfer process. In the experiment, the researchers used many compounds, for example, Methyl 2-(5-bromopyridin-2-yl)acetate (cas: 917023-06-4Related Products of 917023-06-4).

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some tips on 917023-06-4

At the same time, in my other blogs, there are other synthetic methods of this type of compound,917023-06-4, Methyl 2-(5-bromopyridin-2-yl)acetate, and friends who are interested can also refer to it.

Synthetic Route of 917023-06-4, 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. 917023-06-4, name is Methyl 2-(5-bromopyridin-2-yl)acetate. A new synthetic method of this compound is introduced below.

A single-necked round-bottomed flask was charged with Compound 2 (1.80g, 7.82mmol), 3-fluorobenzylamine (2.94g, 23.5mmol), and anhydrous anisole 05g). The reaction was stirred at 150C until reaction was complete LCMS (~23h) and then allowed to cool to near RT. Crystals of the desired product, Compound 3, formed during the cooling process and were collected by filtration and washed with toluene. Compound 3 was obtained as colorless crystalline solid (1.59g, 63% yield) and characterized by 1H NMR (400MHz, DMSO-d6): 3 ,69 (s, 2H), 4,30 (d, 2H), 7.0-7.15 (m, 3H), 7.3-7.4 (m, 2H), 7.99 (dd, 1H), 8.61 (fine d, 1H), 8.66 (br t, 1H),

Reference:
Patent; ATHENEX, INC.; SMOLINSKI, Michael P.; NASIEF ABDEL-SAYED, Nader N.; HANGAUER, JR., David G.; (197 pag.)WO2018/31988; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Extracurricular laboratory: Synthetic route of 917023-06-4

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 917023-06-4, Methyl 2-(5-bromopyridin-2-yl)acetate.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 917023-06-4, name is Methyl 2-(5-bromopyridin-2-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows. name: Methyl 2-(5-bromopyridin-2-yl)acetate

To a solution of methyl 2-(5-bromopyridin-2-yl)acetate (5.50 g, 23.91 mmol) and 1,4- dioxaspiro[4.5]decan-8-ylmethyl trifluoromethanesulfonate (6.85 g, 19.13 mmol) in THF (100 mL) was added LiHMDS (27.50 mL, 27.50 mmol, 1 M in THF) at -78C. The reaction mixture was stirred at 15C for 16 h under a nitrogen atmosphere. LC-MS showed the reaction was complete. The mixture was quenched with saturated NH4Cl solution (30 mL), diluted with water (60 mL), and extracted with EtOAc (50 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, 0-20% EtOAc/PE) to give the title compound.1H NMR (CDCl3, 400 MHz^^^^^^^^^^G^^J=2.0 Hz, 1H), 7.76 (dd, J=8.4, 2.2 Hz, 1H), 7.20 (d, J=8.6 Hz, 1H), 3.85-3.94 (m, 5H), 3.66 (s, 3H), 2.00-2.05 (m, 1H), 1.79-1.87 (m, 1H), 1.61-1.75 (m, 4H), 1.37-1.47 (m, 2H), 1.17-1.29 (m, 3H). MS (ESI) m/z 384.1/386.1 (M+H).

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; KUANG, Rongze; KUMAR, Puneet; DUFFY, Joseph, L.; ZHU, Cheng; ALI, Amjad; YANG, Meng; DEBENHAM, John, S.; (124 pag.)WO2018/39094; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem