1289093-31-7 | Pyridine-derivatives

Luo, Guanglin’s team published research in Journal of Medicinal Chemistry in 2019 | CAS: 1289093-31-7

5-Bromo-3-chloro-2-isobutoxypyridine(cas: 1289093-31-7) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Safety of 5-Bromo-3-chloro-2-isobutoxypyridine

Luo, Guanglin; Chen, Ling; Easton, Amy; Newton, Amy; Bourin, Clotilde; Shields, Eric; Mosure, Kathy; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick L.; Post-Munson, Debra J.; Wang, Shuya; Herrington, James; Graef, John; Newberry, Kimberly; Sivarao, Digavalli V.; Senapati, Arun; Bristow, Linda J.; Meanwell, Nicholas A.; Thompson, Lorin A.; Dzierba, Carolyn published an article on February 28 ,2019. The article was titled 《Correction to Discovery of Indole- and Indazole-acylsulfonamides as Potent and Selective NaV1.7 Inhibitors for the Treatment of Pain [Erratum to document cited in CA172:289998]》, and you may find the article in Journal of Medicinal Chemistry.Safety of 5-Bromo-3-chloro-2-isobutoxypyridine The information in the text is summarized as follows:

In Table 2, line 1, column 8 should be “”μM”” instead of “”nM””. In the experimental materials used by the author, we found 5-Bromo-3-chloro-2-isobutoxypyridine(cas: 1289093-31-7Safety of 5-Bromo-3-chloro-2-isobutoxypyridine)

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

DiMauro, Erin F.’s team published research in Journal of Medicinal Chemistry in 2016 | CAS: 1289093-31-7

Formula: C9H11BrClNOOn September 8, 2016 ,《Application of a Parallel Synthetic Strategy in the Discovery of Biaryl Acyl Sulfonamides as Efficient and Selective NaV1.7 Inhibitors》 was published in Journal of Medicinal Chemistry. The article was written by DiMauro, Erin F.; Altmann, Stephen; Berry, Loren M.; Bregman, Howard; Chakka, Nagasree; Chu-Moyer, Margaret; Bojic, Elma Feric; Foti, Robert S.; Fremeau, Robert; Gao, Hua; Gunaydin, Hakan; Guzman-Perez, Angel; Hall, Brian E.; Huang, Hongbing; Jarosh, Michael; Kornecook, Thomas; Lee, Josie; Ligutti, Joseph; Liu, Dong; Moyer, Bryan D.; Ortuno, Daniel; Rose, Paul E.; Schenkel, Laurie B.; Taborn, Kristin; Wang, Jean; Wang, Yan; Yu, Violeta; Weiss, Matthew M.. The article contains the following contents:

The majority of potent and selective hNaV1.7 inhibitors possess common pharmacophoric features that include a heteroaryl sulfonamide headgroup and a lipophilic aromatic tail group. Recently, reports of similar aromatic tail groups in combination with an acyl sulfonamide headgroup have emerged, with the acyl sulfonamide bestowing levels of selectivity over hNaV1.5 comparable to the heteroaryl sulfonamide. Beginning with com. available carboxylic acids that met selected pharmacophoric requirements in the lipophilic tail, a parallel synthetic approach was applied to rapidly generate the derived acyl sulfonamides. A biaryl acyl sulfonamide hit from this library was elaborated, optimizing for potency and selectivity with attention to physicochem. properties. The resulting novel leads are potent, ligand and lipophilic efficient, and selective over hNaV1.5. Representative lead I demonstrates selectivity over other human NaV isoforms and good pharmacokinetics in rodents. The biaryl acyl sulfonamides reported herein may also offer ADME advantages over known heteroaryl sulfonamide inhibitors. In the experiment, the researchers used 5-Bromo-3-chloro-2-isobutoxypyridine(cas: 1289093-31-7Formula: C9H11BrClNO)

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

9/23/21 News The important role of 1289093-31-7

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1289093-31-7, its application will become more common.

Electric Literature of 1289093-31-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1289093-31-7 as follows.

Preparation 14: methyl 1 -i5-chloro-6-isobutoxypyridin-3-yl)-3-cvclopropyl-1 H- indazole-5-carboxylate; A mixture of methyl 3-cyclopropyl-1 H-indazole-5-carboxylate [preparation 9] (100mg, 0.396mmol), Cul (7.6mg, 0.40mmol), K3P04 (168mg, 0.792mmol), and 5-bromo-3- chloro-2-isobutoxy-pyridine [preparation 30] (105mg, 0.396mmol) was added to a septum sealed reaction vial and degassed. A solution of trans-N, N’- dimethylcyclohexane-1 ,2-diamine in toluene (2ml) was added. The mixture was degassed and filled with nitrogen three times, then stirred at 1 10C for 4 days. The mixture was allowed to cool and then partitioned between water (5ml) and DCM (5ml). The DCM phase was separated and the aqueous extracted with further DCM (5ml). The extracts were combined and evaporated onto silica. Purification by column chromatography (ISCO Companion, silica 12g, eluted with a gradient of heptane to 40% EtOAc in heptane) gave the title compound as clear oil (100.4mg).1 H NMR (400 MHz, CDCI3) delta ppm 1 .07 (d, 6H), 1 .19-1 .12 (m, 4H), 2.18 (septuplet, 1 H), 2.27-2.34 (m, 1 H), 3.97 (s, 3H), 4.21 (d, 2H), 7.55 (dd, 1 H), 7.98 (d, 1 H), 8.09 (dd, 1 H), 8.35 (d, 1 H), 8.58 (dd, 1 H).LCMS (Method A5) Rt 1 .83 min, MS m/z 400 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1289093-31-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; BELL, Andrew Simon; DE GROOT, Marcel John; LEWTHWAITE, Russell Andrew; MARSH, Ian Roger; SCIAMMETTA, Nunzio; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/95781; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 1289093-31-7

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1289093-31-7, 5-Bromo-3-chloro-2-isobutoxypyridine, and friends who are interested can also refer to it.

Application of 1289093-31-7, 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. 1289093-31-7, name is 5-Bromo-3-chloro-2-isobutoxypyridine. A new synthetic method of this compound is introduced below.

Preparation 32: 3-Chloro-2-isobutoxy-5-(4 A5,5-tetramethyl-H ,3,21dioxaborolan-2- -pyridine; Method (i):; To a dry flask was added 5-bromo-3-chloro-2-isobutoxy-pyridine [preparation 30] (825mg, 3.12mmol), KOAc (918mg, 9.35mmol), bis- pinocolatodiboronate (989mg, 3.90mmol) and Pd(dppf)2CI2 (127mg, 0.156mmol) followed by DMF (10ml). The mixture was degassed twice by evacuating and filling with nitrogen and heated at 80C for 6 hours under nitrogen. The reaction mixture was partitioned between EtOAc (30ml) and water (30ml), and the organics washed with brine (20ml), dried over MgS04, filtered and concentrated in vacuo. Purification by column chromatography (ISCO Companion, 40g, heptane – 30% EtOAc:heptane) gave the desired product as a colourless oil (227mg).1 H NM (400 MHz, CDCI3) delta ppm 1 .04 (d, J=6.64 Hz, 6 H) 1 .34 (s, 12 H) 2.09 – 2.21 (m, 1 H) 4.18 (d, J=6.64 Hz, 2 H) 7.97 (d, J=1 .56 Hz, 1 H) 8.37 (d, J=1 .56 Hz, 1 H) impurities present

Sources of common compounds: 1289093-31-7

The synthetic route of 1289093-31-7 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1289093-31-7, name is 5-Bromo-3-chloro-2-isobutoxypyridine, the common compound, a new synthetic route is introduced below. name: 5-Bromo-3-chloro-2-isobutoxypyridine

To a mixture of 6-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carbonitrile (step 5) (220 mg, 1.2 mmol) in dioxane (20 ml) was added 5-bromo-3-chloro-2-isobutoxypyridine (intermediate A) (980 mg, 3.7 mmol), CuI (470 mg, 2.5 mmol), K2CO3 (341 mg, 2.5 mmol), and DMEDA (260 mg, 2.5 mmol). After addition, the mixture was degassed and charged with N2 three times. Then the mixture was heated to 110 C. and stirred at that temperature under N2 atmosphere for 16 hrs. When LC/MS indicated the starting material was consumed, the reaction mixture was diluted with DCM (200 ml). The mixture was filtered over celite. The filtration was washed with brine (*3), dried over anhydrous Na2SO4 and filtered. The filtration was evaporated to afford a residue, which was purified by flash column chromatography on silica gel using a gradient 0-20% ethyl acetate in hexanes to afford the title compound as white solid. LC-MS: Rt=1.27 mins; MS m/z [M+H]+ 362.0; Method 5-95AB 1.5minLC_v003 1H NMR (400 MHz, CDCl3) delta 7.96 (1H, d), 7.56 (1H, d), 6.98 (1H, d), 6.22 (1H, d), 4.31 (2H, m), 4.11 (2H, d), 3.68 (2H, m), 2.16 (1H, m), 1.05 (6H, d).

The synthetic route of 1289093-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEN, Shuhui; HE, Haiyang; LAGU, Bharat; QIN, Hua; WU, Chengde; XIAO, Yisong; US2015/183802; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem