Category: pyridine-derivatives

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. 139585-48-1, name is 2-Chloro-5-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-5-methoxypyridine

a) 5′-Methoxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester To a stirred solution of piperidine-4-carboxylic acid ethyl ester (0.52 g, 3.34 mmol) and 2-chloro-5-methoxy-pyridine in 10 mL of toluene was added (13 mg, 0.057 mmol) of Pd(II) acetate, (17 mg, 0.027 mmol) of BINAP and tBuOK (0.44 g, 3.90 mmol). The mixture was heated at 120 C. for two hours, concentrated under vacuo and the residue was directly purified on column chromatography (SiO2, EtOAc/Hept 1:2) yielding 0.17 g (24%) of the title compound as a light yellow oil. ES-MS m/e: 265.3 (M-41′).

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, 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Patent; Jablonski, Philippe; Knust, Henner; Nettekoven, Matthias; Patiny-Adam, Angelique; Ratni, Hasane; Riemer, Claus; US2011/53948; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 69045-83-6 ,Some common heterocyclic compound, 69045-83-6, molecular formula is C6H2Cl5N, 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.

Take intermediate 2,3-dichloro-5-trichloromethylpyridine 50g,After adding the catalyst, the temperature is raised to 170C.Slowly introduce anhydrous hydrogen fluoride gas,Reaction 11h, after the end of the reaction, neutralized with 5% sodium bicarbonate solution,Separate the organic phase, washed,The crude product obtained after drying was 2,3-dichloro-5-trifluoromethylpyridine as the desired material in an amount of 85% and the yield was 65%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 69045-83-6, 2,3-Dichloro-5-(trichloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong Eastern Countries Nong Pharmaceutical Ji Industrial Co., Ltd.; Yu Lexiang; Li Yuan; Liu Weihua; Sun Meixin; Sun Fujiang; (7 pag.)CN106748985; (2017); A;,
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. 849067-97-6, name is (1H-Pyrrolo[2,3-b]pyridin-5-yl)methanol, the common compound, a new synthetic route is introduced below. name: (1H-Pyrrolo[2,3-b]pyridin-5-yl)methanol

B. lH-Pyrrolo[2,3-b]pyridine-5-carbaldehyde.; (1H-Pyrrolo[2,3- b]pyridin-5-yl)methanol (crude from previous reaction) was dissolved in anhydrous methylenechloride (50 mL). Pyridiniumchlorochromate (3.70 g, 17.0 mmol) was added to the solution and stirred at room temperature overnight. The reaction mixture was filtered through silica gel and washed with ethyl acetate. Organics were poured into water (150 mL), extracted with EtOAc (4×100 mL), combined organic layers were dried with sodium sulfate, and concentrated under reduced pressure to afford the title compound (0.72 g, 4.93 mmol, 87percent over 2 steps) as a white solid. MS (ESI) m/z 147.1 [M+ 1]+.

The synthetic route of 849067-97-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); 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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine

A stirred solution of 20% n-butyl magnesium chloride (63 mL, 127.2 mmol, 1.1 eq) in THF (50 mL) was cooled to 0 C and n-butyl lithium (48 mL, 115.8 mmol, le q, 2.5M in hexane) was added. The resulting reaction mixture was stirred for 10 mm, then diluted with THF (100 mL), cooled to -78 C and a solution of 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (30 g, 115.8 mmol, 1 eq) in THF (50 mL) was added. The reaction mixture was stirred for lh at -78 C. The mixture was quenched with crushed dry ice and allowed to warm to RT and stirred for 16 h. TLC analysis indicated the formation of a polar spot. The reaction mixture was concentrated, acidified with 2N HC1 (80 mL) and extracted with EtOAc (2 x 500 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was recrystallized from n-pentane (30 mL) and dried on high vacuum to give 6-chloro-4-(trifluoromethyl)nicotinic acid (14 g, 53.8% yield) as off white solid. LCMS: [M+Hj 226.29.

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, 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; PROPELLON THERAPEUTICS INC.; AL-AWAR, Rima; ISAAC, Methvin; JOSEPH, Babu; LIU, Yong; MAMAI, Ahmed; PODA, Gennady; SUBRAMANIAN, Pandiaraju; UEHLING, David; WILSON, Brian; ZEPEDA-VELAZQUEZ, Carlos Armando; (311 pag.)WO2019/46944; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1839-17-4, 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. 1839-17-4, name is N4-Methylpyridine-3,4-diamine. A new synthetic method of this compound is introduced below.

Example 121C1 ,2-Dimethyl- lH-imidazo[4,5-c]pyridine[00747] The solution of N4-methylpyridine-3,4-diamine (2.5 g, 20.3 mmol) in acetic anhydride (25 mL) was refluxed overnight. Then acetic anhydride was evaporated under reduced pressure and 1 N hydrochloride acid was added. Then the mixture was extracted with dichloromethane (50 mL x 3). The aqueous layer was neutralized with sodium bicarbonate, and extracted with dichloromethane (50 mL x 3). The organic layers were concentrated to give the title compound (1.9 g, yield 64%). LC-MS (ESI) m/z: 148 (M+l)+. ^-NMR (400 MHz, CDC13) delta (ppm): 2.64 (s, 3H), 3.74 (s, 3H), 7.23-7.24 (d, J= 5.2 Hz, 1H), 8.39-8.41 (d, J= 5.2 Hz, 1H), 8.98 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1839-17-4, N4-Methylpyridine-3,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; WO2011/130661; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 955372-86-8, 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 955372-86-8 as follows.

Step 2: Preparation of methyl 3-bromo-5-fluoroisonicotinate TMSCHN2 (180 mL, 360 mmol, 2 equiv) was added into a solution of 3-bromo-5-fluoroisonicotinic acid (40 g, 182 mmol, 1 equiv), THF (240 mL), and MeOH (80 mL) dropwise with stirring at 0 C. under nitrogen. The resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1/9) to afford the title compound (35 g, 83%) as yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,955372-86-8, its application will become more common.

Reference:
Patent; Genentech, Inc.; Terrett, Jack Alexander; Chen, Huifen; Constantineau-Forget, Lea; Larouche-Gauthier, Robin; Lepissier, Luce; Beaumier, Francis; Dery, Martin; Grand-Maitre, Chantal; Sturino, Claudio; Volgraf, Matthew; Villemure, Elisia; (138 pag.)US2019/284179; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 167884-17-5, Adding some certain compound to certain chemical reactions, such as: 167884-17-5, name is Imidazo[1,2-a]pyridin-5-ylmethanol,molecular formula is C8H8N2O, 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 167884-17-5.

(5) Imidazo[1,2-a]pyridine-5-carbaldehyde Ethyl imidazo[1,2-a]pyridine-5-carboxylate (824 mg) was dissolved in methylene chloride (40 mL). Diisobutylaluminum hydride (1 M solution in toluene) (5 mL) was added at -78C and the mixture was stirred at – 78C for two hours. Diisobutylaluminum hydride (1 M solution in toluene) (10 mL) was further added to the mixture, followed by stirring at -78C for two hours. Methanol (1 mL) was added to the reaction mixture at – 78C, followed by addition of a 20% (+)-potassium sodium tartrate solution. After stirring at room temperature, the reaction mixture was filtered through celite and washed with methylene chloride, followed by extraction with methylene chloride twice. The organic layers were combined, washed with a saturated sodium chloride solution and then dried over magnesium sulfate. The drying agent was removed by filtration and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in acetone (15 mL). 80% manganese dioxide (3 g) was added and the mixture was stirred at room temperature for 11 hours and 20 minutes. The reaction mixture was filtered and washed with acetone. The solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol) to obtain the title compound (96 mg). 1H-NMR (400 MHz, CDCl3) delta(ppm): 7.35-7.44 (m, 1H), 7.53 (d, J=6.8 Hz, 1H), 7.88 (s, 1H), 7.99 (d, J=8.8 Hz, 1H) , 9.04 (s, 1H) , 9.92 (s, 1H) .

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2017275; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 582303-10-4, (2,6-Dimethylpyridin-3-yl)methanol, 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, 582303-10-4, blongs to pyridine-derivatives compound. Product Details of 582303-10-4

To a mixture of methyl (4- (difluoromethyl) -6-hydroxy-l- benzothiophen-3-yl) acetate (78 mg) and THF (dry) (2 mL) were added (2, 6-dimethylpyridin-3-yl) methanol (43.2 mg) , tri-n- butylphosphine (0.212 mL) and ADDP (94 mg) at room temperature. The mixture was stirred at room temperature for 2 h. To the mixture were added ADDP (94 mg) and tri-n-butylphosphine (0.212 mL) , and the mixture was stirred at room temperature for 30 min. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by short pad of silica gel (EtOAc/hexane ) . To a mixture of the residue and THF (2 mL) was added IN NaOH (1 mL) at room temperature. The mixture was stirred at room temperature for 16 h. The mixture was neutralized with IN HCl at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgS04 and concentrated in vacuo. The crude product was purified by preparative HPLC (C18, H20/CH3CN (including 10 mM NH4HC03) ) . The fraction was extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgS0 and concentrated in vacuo. The residue was crystallized from EtOAc-hexane to give the title compound (29.1 mg) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,582303-10-4, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKAKURA, Nobuyuki; BANNO, Yoshihiro; TERAO, Yoshito; OCHIDA, Atsuko; MORIMOTO, Sachie; KITAMURA, Shuji; TOMATA, Yoshihide; YASUMA, Tsuneo; IKOMA, Minoru; MASUDA, Kei; WO2013/125732; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1796-84-5, 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. 1796-84-5, name is 4-Ethoxy-3-nitropyridine, molecular formula is C7H8N2O3, 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 solution consisting of 4-ethoxy-3-nitropyridine (15.0 g, 97.3 mmol) and EtNH2 (46.5 mL, 70% aq. solution, 584 mmol) in EtOH (30 mL) was stirred at 85 C in a pressure vessel for 2 h. Removal of all volatiles in vacuo afforded the title compound (16.2 g, 99 %). MS (ES+) m/z 168 (M+H) +.

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 1796-84-5, 4-Ethoxy-3-nitropyridine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/46678; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 97004-04-1, 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.97004-04-1, name is (6-Chloropyridin-3-yl)methanamine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

EXAMPLE 29 To a mixture of O-methyl-N-nitroisourea (1.25 g, 10.53 mmol), water (20 ml) and concentrated hydrochloric acid (0.85 ml, 10.03 mmol) was added 5-(aminomethyl)-2-chloropyridine (1.43 g, 10.03 mmol) dropwise over 5 minutes at room temperature with stirring. The reaction mixture was neutralized with 40% aqueous sodium hydroxide solution and adjusted to pH 7.2. After 17 hours of stirring at room temperature, the resulting crystals were collected. The crystals were washed with water and dried. As a result, 1.16 g (47.3% yield) of O-methyl-N-(6-chloro-3-pyridylmethyl)-N’-nitroisourea was obtained as white crystals. M.p. 112-113 C. 1 H-NMR (CDCl3) delta: 3.98 (3H, s), 4.57 (2H, d, J=6.0 Hz), 7.38 (1H, d, J=8.2 Hz), 7.63 (1H, dd, J=8.2 Hz, 2.4 Hz), 8.36 (1H, d, J=2.4 Hz), 9.43 (1H, br). IR (nujol): 3250, 1590, 1520, 1390, 1240, 1210 (cm-1).

The chemical industry reduces the impact on the environment during synthesis 97004-04-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6008363; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem