Category: 867279-13-8

Electric Literature of 867279-13-8, 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. 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. A new synthetic method of this compound is introduced below.

To a solution of 4-bromo-2-chloro-5-methylpyridine (0.15 g, 0.73 mmol) in DCM (5 ml) was added 77% mCPBA (0.33 g, 1.45 mmol). The resulting mixture was stirred at rt for 3 days. EtOAc was added followed by 1 : 1 mixture of Na2SO3 and Na2CO3 solutions. The resulting mixture was stirred vigorously for 0.5 hour and the organic phase was separated. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with aq. ‘Na2C03 solution and brine, dried with Na2S04, filtered and evaporated yielding 0.13 g of 4-bromo-2-chloro-5-methylpyridine 1 -oxide. 1H NMR (CDCi3) delta: 8.20-8.23 (m, 1 1 1), 7.66 (s, 1-Iota), 2.31-2.34 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Bromo-2-chloro-5-methylpyridine

A mixture of 66 (0.35g, 1.02mmol), 4-bromo-2-chloro-5-methylpyridine (0.32g, 1.53mmol) and K3PO4 (0.43g, 2.04mmol) in dioxane (15mL) was exchanged with argon twice, then PdPPh3)4 (0.11g, 0.1mmol) were added to the above mixture. The reaction mixture was heated to 100C and stirred for 4h under argon atmosphere. The mixture was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in 74 petroleum ether 5%) to give the product as a white solid (0.3g, yield=69%). 1H NMR (400MHz, CDCl3) delta 8.25 (s, 1H), 7.64 (m, 2H), 7.19 (s, 1H), 4.07 (d, J=7.0Hz, 2H), 3.99 (dd, J=11.3, 3.2Hz, 2H), 3.35 (td, J=11.8, 2.1Hz, 2H), 2.49 (s, 3H), 2.22-2.16 (m, 1H), 1.60 (s, 9H), 1.50-1.42 (m, 3H). LC/MS (ESI, m/z) 424.14 [M+H]+.

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, 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine.

Reference:
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, 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, Recommanded Product: 867279-13-8, blongs to pyridine-derivatives compound. Recommanded Product: 867279-13-8

Intermediate 8 (0496) 1-terf-But l 2-methyl 4-(2-chloro-5-methylpyridin-4-yl)- IH-pyrrole- 1 ,2-dicarboxylate (0497) (0498) Pd(Ph3P)4 (2.80 g, 2.42 mmol) was added to 1-tert-butyl 2-methyl 4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-lH-pyrrole-l,2-dicarboxylate (17.01 g, 48.43 mmol), 4-bromo-2- chloro-5-methylpyridine (10 g, 48.43 mmol) and Na2C03 (10.27 g, 96.87 mmol) in 1,4- dioxane (150 mL),water (30 mL) at 20 C under nitrogen. The resulting solution was stirred at 80 C for 4 hours. The reaction mixture was poured into water (200 mL), extracted with EtOAc (3 x 200 mL), the organic layer was dried over Na2S04, filtered and evaporated to afford yellow oil. The crude product was purified by flash silica (0499) chromatography (elution gradient 9 to 10% EtOAc in petroleum ether). Pure fractions were evaporated to dryness to afford l-tert-butyl 2-methyl 4-(2-chloro-5-methylpyridin-4-yl)- lH-pyrrole-l,2-dicarboxylate (Intermediate 8; 7.80 g, 45.9%) as a colourless oil. FontWeight=”Bold” FontSize=”10″ Eta NMR (300 MHz, CDC1 ) delta 1.64 (9H, s), 2.41 (3H, s), 3.91 (3H, s), 7.05 (1H, s), 7.32 (1H, s), 7.55 (1H, s), 8.25 (1H, s). m/z (ES+), [M+H]+ = 351.

The synthetic route of 867279-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; FERON, James, Lyman; (80 pag.)WO2017/80980; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 867279-13-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-(4,4,5,5-Tetramethyl- [1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H pyrrole-2- carboxylic acid methyl ester (125 mg, 0.29 mmol, 0.6 equiv. ) and 4-bromo-2- chloro-5-methylpyridine (96 mg, 0.47 mmol, 1.0 equiv. ) were dissolved in benzene (4 mL). After adding methanol (0.94 mL) and aqueous Na2C03, Pd (PPh3)4 (108 mg, 0.094 mol, 0.2 equiv. ) was then added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. After drying the organic layer over Na2S04, the solvent was removed under reduced pressure. The crude material was purified by reversed phase HPLC (acetonitrile/ water/TFA), yielding the title compound as a colorless solid (54 mg, 0.125 mmol, HPLC Rt 9.087 min, ES+ 433.0, ES- 431.0).

According to the analysis of related databases, 867279-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS, INCORPORATED; WO2005/100342; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5BrClN

General procedure: General Procedure A: (0312) A mixture of an arylbromide or aryliodide (1 mmol), an arylboronic acid, aryldioxaborolane or bis(pinacolato)diboron (1.5 mmol), a palladium catalyst (0.1 mmol) and K2CO3 (2-3 mmol) was placed in a reaction vessel which was then thoroughly purged with argon. Dioxane (3 mL) and water (1.5 mL) were added, and the mixture was stirred at 80-95 C. for 1 to 4 h. After cooling to rt, the mixture was poured into EtOAc/H2O (1:1, 10 mL) and the aqueous layer was extracted with EtOAc (5 mL×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the resultant residue by silica gel chromatography (EtOAc/heptanes) afforded the desired biaryl product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Player, Mark R.; Huang, Hui; Winters, Michael P.; (98 pag.)US2017/291908; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 867279-13-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-Bromo-2-chloro-5-methylpyridine (600 mg, 2.9 mmol) was added to a mixture of4-(tert-butyl)-1H-imidazole (431 mg, 3.48 mmol) and C52CO3 (2.83 g, 8.7 mmol) in DMF (2 mL). The resulting solution was stirred at 100C overnight. The mixture was cooled to rt, diluted with EtOAc (100 mL), and washed with water (3OmLx2) and brine (3OmL). The organic layer was dried over Na2504, filtered, and concentrated in vacuo. Purification of theresidue on a silica gel column with 30% EtOAc/PE provided 400 mg (55%) of 4-(4-(tert- butyl)- 1H-imidazol- 1 -yl)-2-chloro-5 -methyl pyridine as a light yellow solid.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WANG, Guoqiang; SHEN, Ruichao; LONG, Jiang; MA, Jun; XING, Xuechao; HE, Yong; GRANGER, Brett; HE, Jing; WANG, Bin; OR, Yat, Sun; (125 pag.)WO2018/209354; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, 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, Safety of 4-Bromo-2-chloro-5-methylpyridine, blongs to pyridine-derivatives compound. Safety of 4-Bromo-2-chloro-5-methylpyridine

Step 3: To a solution 4-bromo-2-chloro-5-methylpyridine (75 g, 363 mmol) in THF (500 mL) was added isopropylmagnesium chloride lithium chloride (1397 mL of 1.3M solution in THF,1816 mmol) at 0 C, The resulting mixture stirred at 22 C for 1 h. Then, the resulting mixture was stirred at 22 C under CO2 (1 atm) for 40 mm. The mixture was quenched with H20 (1500 mL) and extracted with EtOAc (300 mL x 2). The aqueous phase was adjusted to pH 5 withM aqueous HC1 and then was extracted with EtOAc (300 mL x 3). The resulting organic layers were washed with brine (300 mL) and concentrated in vacuum to give 2-chloro-5-methylisonicotinic acid as a light yellow solid, which was used directly in next step without further purification. MS: 172 (M + 1). ?H NMR (400 MHz, DMSO-d6) 8.39 (s, 1H), 7.68 (s, 1H), 2.43 (s, 3H).

The synthetic route of 867279-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CTXT PTY. LTD.; MACHACEK, Michelle, R.; WITTER, David, J.; REUTERSHAN, Michael Hale; ALTMAN, Michael, D.; STUPPLE, Paul Anthony; (67 pag.)WO2019/94311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 867279-13-8 , The common heterocyclic compound, 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine, molecular formula is C6H5BrClN, 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 stirred solution of 4-bromo-2-chloro-5-methylpyridine (2 g, 9.69 mmol, 1 equiv.) in t- BuOH (15 mL) was added t-BuONa (2.0 g, 20.34 mmol, 2.1 equiv.) at room temperature. The final reaction mixture was irradiated with microwave radiation for 5 h at 120 degrees C. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The reaction solution was acidified to pH 6 with HCl (aq.1M). The resulting mixture was extracted with CH2Cl2(3 x 50 mL). The combined organic layers were washed with brine (1×100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions (Column: C18 Column 330 g; Mobile Phase A: Water (10 mmol/L AcOH), Mobile Phase B: ACN; Flow rate: 80 mL/min; Gradient: 10% B to 30% B in 40 min; 254/220 nm) to afford 4- bromo-5-methylpyridin-2-ol(1.2g,65.89%) as an off-white solid.

The synthetic route of 867279-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem