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

Electric Literature of 1137-67-3, Adding some certain compound to certain chemical reactions, such as: 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole,molecular formula is C12H9N3, 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 1137-67-3.

, weighing 0.25g cobalt chloride hexahydrate,0.2 g of 2- (3-pyridyl) benzimidazole,0.2 g of 1,3-benzenedicarboxylic acid and 15 mL of water in a 50 mL flask,The flask was placed on a magnetic stirrer and stirred for 30 minutes.(2)The mixed homogeneous solution was transferred to a 25 mL autoclave.,The autoclave was placed in an oven,Heated from room temperature to 170 C at a rate of 1 C / min,At this temperature for 72h,And then to 5 / h rate down to room temperature,Solid-liquid separation is shown in Figure 1-3,The dinuclear cobalt complex shown in Figures 4-6,The yield was about 65%.

According to the analysis of related databases, 1137-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Heifei University; Zhang, Quanzheng; Cheng, Xuan; Ding, Dong; Chen, Ying; (13 pag.)CN103923126; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 36953-37-4, 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 36953-37-4, name is 4-Bromopyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Example 26i 4-Bromo-2-(difluoromethoxy)pyridine 4-Bromopyridin-2(1H)-one (200 mg, 1.15 mmol) and sodium 2-chloro-2,2-difluoroacetate (210 mg, 1.38 mmol) were slurried in dry acetonitrile (8 mL). The mixture was refluxed overnight, allowed to cool to r.t. and directly extracted with pentane (3*5 mL). The combined organic phases were evaporated to give 219 mg (85% yield) of the title compound: 1H-NMR (500 MHz DMSO-d6) delta 8.18 (d, 1H), 7.70 (t, 1H), 7.56 (d, 1H), 7.50 (s, 1H); MS (CI+) m/z 226 224 [M+1]+

According to the analysis of related databases, 36953-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/125087; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1187322-51-5, 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. 1187322-51-5, name is 6-Amino-5-iodonicotinonitrile. A new synthetic method of this compound is introduced below.

To the degassed mixture of 6-amino-5-(prop-l -yn-l-yl)pyridine-3-carbonitrile (329 mg, 1.34 mmol), bis'(triphenylphosphine)dichloropailadium(0) (95 mg, 0.134 mmol), copper (I) iodide (128 mg, 0.671 mmol) and triethylamine (976 mg, 1.34 mL, 9.64 mmol) in ahs. THF (18 mL) a propyn solution (3-4 % in THF; 13.2 mL) was added via septum at 0-5 C. The mixture was stirred for 30 minutes at 0-5 C, then for a further 18 hours at room temperature. The reaction was quenched by the addition of NFLCl solution. The solid was removed by filtration and the cake was washed with CH2CI2. The combined organic layer was dried with anhydrous NaiSOr, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica, eluted by 40 % EtOAc in cyclohexane to give 150 mg of the title compound as a yellow solid (71 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1187322-51-5, 6-Amino-5-iodonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; ELES, Janos; DUDASNE MOLNAR, Katalin; LEDNECZKI, Istvan; TAPOLCSANYI, Pal; HORVATH, Anita; NEMETHY, Zsolt; LEVAY, Gyoergy Istvan; (0 pag.)WO2020/12422; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 95652-80-5, 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 95652-80-5 as follows.

To a stirred solution of 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.To a suspension of the crude material including 12and NaOAc (3.78 g, 46.1 mmol) in the 1 : 1 mixture of n-BuOH and toluene (total 120 mL) was added Pd(dppf) Cl2 (1.12 g, 1.54 mmol) at room temperature. The resulting mixture was stirred under ordinary CO pressure (balloon) at 100C for 18 h. The reaction was quenched with saturated aqueous NH4Cl, filtered through a pad of Celite and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, n-hexane-EtOAc=2 : 1) to afford 13(4.75 g, 65% 2 steps) as a yellow oil.13: IR (film, cm-1): 2963, 2876, 1721, 1692, 1595, 1481, 1337, 1277, 1261, 1219, 1138, 1072, 1022; 1H-NMR (CDCl3, 500 MHz) delta: 10.39 (s, 1H), 8.18 (d, J=8.50 Hz, 1H), 6.94 (d, J=8.50 Hz, 1H), 4.44 (t, J=6.80 Hz, 2H), 4.06 (s, 3H), 1.83-1.76 (m, 2H), 1.54-1.45 (m, 2H), 0.99 (t, J=7.37 Hz, 3H); 13C-NMR (CDCl3, 125 MHz) delta: 189.1, 166.1, 165.2, 150.7, 138.6, 125.9, 114.1, 66.3, 54.5, 30.5, 19.2, 13.7; HR-MS (ESITOF): Calcd for C12H15NO4Na [(M+Na)+] 260.0893. Found 260.0891.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,95652-80-5, its application will become more common.

Reference:
Article; Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 723 – 732;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide. This compound has unique chemical properties. The synthetic route is as follows. Formula: C10H13ClN2O

To a solution of N-(6-chloropyridin-2-yl)-2,2-dimethylpropanamide (10.6 g, 50 mmol) in THF (100 mL) n-butyllithium (2.5 M solution in hexane, 50 mL, 125 mmol) was added. The resulting mixture wasstirred at -20C for 3 h. After the addiction of DMF (4 mL) the reaction mixture was allowed to warm to room temperature and then was quenched with 0.5 M HCI. Ethyl acetate was added, the organic phase was washed with water, sat. K2003 and with brine. The crude material was purified by Si-column eluting with cy to cy/ethyl acetate 7:3 toobtain the title product (6.7 g, 27.8 mmol, 56% yield). LC-MS (M-H) =241.3

With the rapid development of chemical substances, we look forward to future research findings about 86847-84-9.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem