Category: pyridine-derivatives

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 766-11-0, name is 5-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 5-Bromo-2-fluoropyridine

Phenol (8.02 g, 85.23 mmol) was dissolved in 50 ml of anhydrous tetrahydrofuran and stirred in an ice bath.Sodium hydride (2.5 g, 113.64 mmol) was gradually added and stirred for 30 min, and the reaction was continued at 80 C for 30 min.After cooling to room temperature, 2-fluoro-5-bromo-pyridine (10 g, 56.82 mmol) was added and refluxed at 80 C for 12 h.After the reaction was completed, it was cooled to room temperature, and the reaction was quenched with 100 ml of water, and extracted with ethyl acetate (100 ml×3).The organic phase was combined, washed with saturated brine, dried, filtered, and evaporated.Silica gel column chromatography gave 12.3 g of colorless oil, yield 86%.The elution system was petroleum ether: ethyl acetate = 100:1.

With the rapid development of chemical substances, we look forward to future research findings about 766-11-0.

Reference:
Patent; Shandong University; Zhao Guisen; Ran Fansheng; Liu Meixia; Liu Yang; Wang Luhua; (48 pag.)CN109369654; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 588729-99-1, 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 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: The 2-chloro-3-amino-5-bromo pyridine (500 mg, 2 . 46mmol) was dissolved in THF (10 ml), added LiHMDS (7.4 ml, 7 . 4mmol), stirring for ten minutes, then adding 4-fluorobenzenesulfonyl chloride (1.44g, 7 . 4mmol), stir at room temperature overnight. By adding dichloromethane (20 ml) dilution, washed with saturated sodium bicarbonate, with dichloromethane (4×30 ml) extraction, combined organic phase, dried, concentrated, the residue column chromatography (petroleum ether: ethyl acetate = 20:1) shall be N-(5-bromo-2-chloro-pyridine-3-yl) – 4-fluorobenzene sulfonaide (770 mg, 87%).

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 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; Shanghai Huilun Life Sciences & Technology Co., Ltd.; Cheng, Jianjun; Qin, Jihong; (61 pag.)CN103936762; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 791644-48-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 791644-48-9, name is 2-Chloro-5-fluoronicotinonitrile, molecular formula is C6H2ClFN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A suspension of 38.5 g (245.93 mmol) of 2-chloro-5-fluoronicotinonitrile was initially charged in 1,2-ethanediol (380 ml), and hydrazine hydrate (119.6 ml) was then added. With stirring, the mixture was heated at reflux for 4 h. The product precipitated on cooling. Water (380 ml) was added to the crystals, and the mixture was subjected to extractive stirring at RT for 10 min. The suspension was then filtered with suction over a frit, and the filter product was washed with water (200 ml) and with -10 C. cold THF (200 ml). Drying under high vacuum over phosphorus pentoxide. Yield: 22.8 g (61% of theory) 1H NMR (400 MHz, DMSO-d6): delta=5.54 (s, 2H), 7.96 (dd, 1H), 8.38 (m, 1H), 12.07 (m, 1H).

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 791644-48-9, 2-Chloro-5-fluoronicotinonitrile.

Reference:
Patent; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Griebenow, Nils; Lang, Dieter; Wunder, Frank; Huebsch, Walter; Vakalopoulos, Alexandros; Tersteegen, Adrian; US2014/357637; (2014); 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.13603-44-6, name is 2,6-Dimethylpyridin-4-ol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.name: 2,6-Dimethylpyridin-4-ol

Alternative procedure: Bromine (72.8 mL, 1.4 mol) was added via addition funnel over60 mm to a mechanically stirred cold (ice-water bath) solution of 2,6-dimethylpyridin-4- ol (87 g, 706 mmol) and 4-methylmorpholine (156 mL, 1.4 mol) in dichloromethane (1 L) and methanol (100 mL) and then stirred for 2 h at rt. Additional bromine (15 mL) was added based on monitoring by LCMS. The product was filtered, washed with ether, anddried under vacuum to give 3,5-dibromo-2,6-dimethylpyridin-4-ol 176.8 g (88%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13603-44-6, 2,6-Dimethylpyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; KADOW, John F.; NAIDU, B. Narasimhulu; WANG, Tao; YIN, Zhiwei; (82 pag.)WO2017/6261; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 944896-42-8 , The common heterocyclic compound, 944896-42-8, name is 6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5BrN2O2, 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 solution of 6-bromoimidazo[l,2-a]pyridine-3-carboxylic acid (50 mg, 0.21 mmol) in DMF (0.5 mL) was added 3-methoxybenzylamine (37 mg, 0.27 mmol) and HATU (95 mg, 0.25 mmol). The resulting mixture was stirred at room temperature overnight. After removal of solvent by rotary evaporation, the residue was dissolved in ethyl acetate (15 mL) and washed with a saturated aqueous Na2C03 solution (2 x 10 mL), and brine (10 mL), dried over Na2S04, and filtered. The solvent was removed in vacuo and the crude amide product was purified by flash chromatography on silica gel to afford the title compound (52 mg, 70%). LC-MS: single peak at 254 nm, MH+ calcd. for C16H15BrN302: 360, obtained: 360.

The synthetic route of 944896-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17228-69-2, 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. 17228-69-2, name is 2-Chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 2-chloro-4-methoxypyridine (10.0 g, 69.7 mmol) in 50 mL of sulfuric acid at 0C was added NBS. The reaction mixture was allowed to stir and warm up to room temperature for 2 h and then heated at 60C for 5 h. Next, the reaction mixture was cooled to room temperature, neutralized with 1 N NaOH (pH 7), diluted with water (50 ml) and the aqueous layer was extracted with ethyl acetate (2 x 100 mL).The organic layers were washed with water (2 x 50 mL), saturated NaHCO3, brine, dried over Mg2SO4 and concentrated to provide an oil, which was chromatographed to give 5-bromo-2- chloro-4-methoxypyridine eluting with 0-25% EtOAc/hexanes. ?HNMR (500 MHz, DMSO-d6) oe 8.4 (s, 1H), 7.29 (s, 1H), 3.97 (s, 3H); LC/MS: [(M+1)] = 223.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17228-69-2, 2-Chloro-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid, the common compound, a new synthetic route is introduced below. Formula: C7H3ClF3NO2

Example 187 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-3-chloro-5-(trifluoromethyl)picolinamide The title compound was synthesized by procedures and steps analogous to those described in Method Z, Example 186 above, but using 3-chloro-5-(trifluoromethyl)-2-pyridine carboxylic acid (Bionet Research). MS m/z=517.1 [M+H]+. Calculated for C19H13ClF8N4O2: 516.77 1H NMR (300 MHz, CHLOROFORM-d) delta=9.82 (br. s., 1H), 8.77 (s, 1H), 8.22-8.08 (m, 2H), 7.10-7.00 (m, 1H), 4.37 (br. s., 2H), 4.04 (dd, J=5.3, 9.7 Hz, 1H), 2.86-2.70 (m, 1H), 1.91 (t, J=13.2 Hz, 1H), 1.64 (s, 3H)

The synthetic route of 80194-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); 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. 37669-64-0, name is 5-Bromo-3-pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H6BrNO

To a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0 C was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was poured onto ice/water (20 mL), basified with NaOH cone. (8 mL) and extracted with EtOAc (2 x 50 mL). Combined organics were dried over Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtO Ac-heptane gradient to give the title compound (3.08 g, 93 %) as a white solid. MS: 206.0, 207.9 (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, 37669-64-0, 5-Bromo-3-pyridinemethanol.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 17920-35-3, name is 2-Amino-6-methoxypyridine, the common compound, a new synthetic route is introduced below. Quality Control of 2-Amino-6-methoxypyridine

A solution of 5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (254.0 mg, 0.75 mmol) and 6-methoxypyridine-2-amine (136.0 mg, 1.10 mmol) in pyridine (10 mL) was stirred for 2 h at 50 °C. The reaction mixture was poured into H2O and the solid was collected by filtration. The crude residue was purified by flash chromatography to give N-(6-methoxypyridin-2-yl)-2-methyl-5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (85.0 mg, 27percent yield). MS (ESI) calcd for C21H16F3N5O2 (m/z): 427.13; found: 428 [M+H

The synthetic route of 17920-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GlaxoSmithKline LLC; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; (583 pag.)EP2768509; (2017); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid. A new synthetic method of this compound is introduced below.

5-Bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example Apollo Scientific) was suspended in DCM (100 mL) and then oxalyl chloride (16.98 mL, 194 mmol) was added, followed by DMF (5.01 mL, 64.6 mmol) and the mixture was stirred for 18 h at rt. The solvent was evaporated in vacuo and the residue was redissolved in DCM (100 mL) and evaporated to dryness to give 5-bromo-2-methoxynicotinoyl chloride (16.33 g, 65.2 mmol, 101 % yield) which was used in the next step immediately. (0454) *H NMR (400 MHz, CDCI3) delta ppm 8.49 (d, J=2.7 Hz, 1 H) 8.44 (d, J=2.4 Hz, 1 H) 4.06 (s, 3 (0455) H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54916-66-4, 5-Bromo-2-methoxynicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen, John; DEMONT, Emmanuel, Hubert; HARRISON, Lee, Andrew; HAYHOW, Thomas, George, Christopher; LINDON, Matthew, J.; PRESTON, Alexander, G.; SEAL, Jonathan, Thomas; WALL, Ian, David; WATSON, Robert, J.; WOOLVEN, James, Michael; (91 pag.)WO2017/60180; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem