Pyridine-derivatives

Electric Literature of 153034-88-9, 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 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-chloro-4-iodo-3-methylpyridine (Aldrich cat724092: 303 mg, 1.20 mmol), phenylboronic acid (160 mg, 1.32 mmol), and sodium carbonate (317 mg, 2.99 mmol) in tert-butyl alcohol (9.5 mL) and Water (5.4 mL) was added bis(di-cyclohexylphosphino)ferrocene]dichloropalladium( II) (181 mg, 0.239 mmol). The reaction was purged with N2, then heated to 80 C. The crude reaction mixture was cooled to room temperature after 2 hours. The crude reaction mixture was diluted with water and extracted with DCM. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude residue was purified by column chromatography (020% ethyl acetate in hexanes). LC-MS calculated for C12H11ClN (M+H)+: m/z 204.1; found: 204.2.

According to the analysis of related databases, 153034-88-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 769-54-0, 3-Fluoro-4-nitropyridine 1-oxide, 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, Product Details of 769-54-0, blongs to pyridine-derivatives compound. Product Details of 769-54-0

Under ice-cooling, 3-fluoro-4-nitropyridine 1-oxide (9.75 g, 61.7 mmol) with the eyeThe mixed suspension of ethanol (145 mL), 28% sodium methoxide methanol solution (11.9 g, 61.7 mmol) was added. The temperature was raised to room temperature, the mixture was stirred at the same temperature for 1 hour. Reduced pressure methanolWas distilled off under Water (50 mL) was added and extracted with chloroform to the residue. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the solvent was evaporated under reduced pressure to obtain the desired product (9.54 g, 91% yield).

The synthetic route of 769-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA LIMITED; KIRIYAMA, KAZUHISA; JUKUROGI, TATSUYA; UMEMOTO, NAO; KANI, TATSUYA; MATSUDA, YOKO; TANAKA, KUMINO; (64 pag.)JP2016/11294; (2016); A;,
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. 42521-09-5, name is Methyl 2,6-dichloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Methyl 2,6-dichloroisonicotinate

Compound 99: 2,6-Dimethyl-isonicotinic acid methyl ester. Under inert atmosphere, a mixture of methyl 2,6-dichloropyridine-4-carboxylate (2,00 g), dimethylzinc (2N in toluene, 14.6 mL, 3.0 equiv.) and PdCl2(dppf)2 (400 mg, 0.05 equiv.) in dioxane (50 mL), was heated at 80C for 4Hrs. The reaction mixture was cooled by an ice bath, hydrolysed with water (100 mL) and filtered through a pad of celite. The pad was rinsed with water and EtAOc. The filtrate was extracted with EtOAc (250 mL). The organic layer was washed with brine (100 mL), dried over MgSO4 and concentrated. Purification by flash-chromatography (MeOH in CH2Cl2, 0 to 2%) afforded compound 99 as an orange oil in 96% yield. 1H-NMR (400 MHz, DMSO): 2.51 (s, 6H, 2CH3); 3.88 (s, 3H, O-CH3); 7.51 (s, 2H, Ar). M/Z (M+H)+ = 166.1.

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, 42521-09-5, Methyl 2,6-dichloroisonicotinate.

Reference:
Patent; Domain Therapeutics; Mayer, Stanislas; Schann, Stephan; EP2666775; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1254163-81-9, name is Methyl 6-chloro-5-cyanopicolinate. A new synthetic method of this compound is introduced below., HPLC of Formula: C8H5ClN2O2

Step 2: Preparation of 5-cyano-6-(1 ,3,5-trimethyl-1 H-pyrazol-4-yl)-pyridine-2- carboxylic acid methyl esterThe title compound may be prepared from 6-chloro-5-cyano-pyridine-2-carboxylic acid methyl ester by reaction with 1 ,3,5-trimethylpyrazol-4-yl boronic acid under Suzuki reaction conditions as described in the previous examples

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, 1254163-81-9, Methyl 6-chloro-5-cyanopicolinate.

Reference:
Patent; NOVARTIS AG; ASTEX THERAPEUTICS LIMITED; HOWARD, Steven; MORTENSON, Paul Neil; HISCOCK, Steven Douglas; WOOLFORD, Alison Jo-Anne; WOODHEAD, Andrew James; CHESSARI, Gianni; O’REILLY, Marc; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; CHO, Young Shin; YANG, Fan; CHEN, Christine Hiu-Tung; BRAIN, Christopher Thomas; LAGU, Bharat; WANG, Yaping; KIM, Sunkyu; GRIALDES, John; LUZZIO, Michael Joseph; PEREZ, Lawrence Blas; WO2010/125402; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1044872-40-3, Adding some certain compound to certain chemical reactions, such as: 1044872-40-3, name is Methyl 2-amino-4,6-dichloronicotinate,molecular formula is C7H6Cl2N2O2, 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 1044872-40-3.

A mixture of dimethyl acetone-1,3-dicarboxylate (200 g, 1.15 mol), cyanamide (48.3 g, 1.15 mol), and Ni(acac)2 (14.75 g, 0.0574 mol) in dioxane (200 mL) was heated to reflux for 16 h and then cooled to room temperature. The precipitate was filtered off, and the solid was mixed with methanol (200 mL) and stirred for 30 min and filtered again to give 93 g product (44% yield). In a 1 L flask with a reflux condenser was added the product from step one (93.0 g, 0.505 mol) and POCl3 (425 mL) and the reaction mixture was heated to reflux for 35 min. POCl3 (300 mL) was evaporated under vacuum. The residue was poured into ice and water (400 mL), which was neutralized with KOH to pH 6-7. The precipitate was filtered off and extracted with ethyl acetate (2×300 mL). The organic solution was concentrated and purified by column chromatography to give methyl 2-amino-4,6-dichloropyridine-3-carboxylate (22.5 g, 20.1%). In a 500 mL flask with reflux condenser was added methyl 2-amino-4,6-dichloropyridine-3-carboxylate (22.5 g, 0.101 mol) and 25 wt % sodium methoxide in methanol (88 mL, 0.407 mol), together with methanol (20 mL). The mixture was heated to reflux for 5 h then cooled to room temperature. Acetic acid (15 mL) was added to the mixture and the pH was adjusted to 7.0. Methanol was removed and the residue was poured into water (100 mL). The precipitated solid was filtered off and rinsed with water (3×200 mL) to give methyl 2-amino-4,6-dimethoxypyridine-3-carboxylate (18.5 g, 86.4%). In a 500 mL flask with a reflux condenser was added methyl 2-amino-4,6-dimethoxypyridine-3-carboxylate (18.5 g, 0.0872 mol), potassium hydroxide (19.5 g, 0.349 mol) in water (80 mL) and ethanol (100 mL). The mixture was heated to 80 C. for 16 h. The solvent was removed and aqueous HCl was used to adjust pH to 6.0. The water was removed by lyophilization. The obtained solid was extracted with methanol to yield 2-amino-4,6-dimethoxy-nicotinic acid in quantitative yield. 2-Amino-4,6-dimethoxy-nicotinic acid (17.2 g, 0.0872 mol) was added to THF (110 mL). 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (21.73 g, 0.113 mol), 1-hydroxybenzotriazole hydrate (12.96 g, 0.0959 mol) and 4-methyl morpholine (9.7 g, 0.0959 mol) were then added to the suspension. After stirring for 10 min at room temperature, 50% v/v ammonium hydroxide (18.3 g, 0.262 mol) was added. The reaction mixture was kept at room temperature for 16 h. THF was removed and the residue was poured into cold water (100 mL). The precipitate was filtered off and further washed with cold water to yield 5.3 g of the pure desired compound. The aqueous solution was further extracted with dichloromethane (3×150 mL) to yield 8.4 g crude product, which was further purified by column chromatography to give a total of 10.8 g (62.8%) of 2-amino-4,6-dimethoxy-nicotinamide.To a solution of 2-amino-4,6-dimethoxy-nicotinamide (1.40 g, 7.1 mmol) and 4-hydroxy-3,5-dimethylbenzaldehyde (1.07 g, 7.1 mmol) in N,N-dimethyl acetamide (20 mL), NaHSO3 (1.39 g, 7.81 mmol) and p-TSA (0.675 g, 3.55 mmol) were added and the reaction mixture was heated at 150 C. overnight. The solvent was removed under reduced pressure. The residue was diluted with water and the solid was collected and further washed with methanol. The crude product was purified by column chromatography (silica gel 230-400 mesh; 2% methanol in CH2Cl2 as eluent) to give 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxypyrido[2,3-d]pyrimidin-4(3H)-one (0.92 g, 39.6%). Selected data: MS (ES) m/z: 328.07; MP 297-299 C.

According to the analysis of related databases, 1044872-40-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wong, Norman C.W.; Tucker, Joseph E.L.; Hansen, Henrik C.; Chiacchia, Fabrizio S.; McCaffrey, David; US2008/188467; (2008); 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. 21190-87-4, name is 6-Bromo-2-pyridinecarboxylic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H4BrNO2

A) 6-(4-Fluorophenyl)picolinic acid A solution of 6-bromopicolinic acid (Aldrich) (2.02 g, 10 mmol) in DME containing 4 mL of 10% aq Na2CO3 was purged with Ar gas. To this mixture was added Pd(PPh3)4 followed by 2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane (2.40 g, 11.5 mmol, Wako Pure Chemical Industries, Ltd) and EtOH (20 mL), and the mixture was purged with Ar gas. The reaction mixture was heated at 100 C. for 2.5 h in a sealed tube. Additional 2-bromopicolinic acid (900 mg) and Pd (OAc)2 was added, and after purging with Ar gas it was heated at 100 C. for 4.5 h. Trifluoroacteic acid (20 mL) was added to the reaction mixture, concentrated and MeOH (150 mL) was added to the residue. The insoluble material was filtered, and the filtrate solution was concentrated. Purification by flash column on silica gel eluding with EtOAc/MeOH//900:100 followed by EtOAc/MeOH/HOAc//700:1500:50 provided the desired product (1.0 g, 40% based on borinane starting material) as a white solid. 1H NMR (CD3OD) delta8.01 (d, 1H, J=7.7 Hz), 7.94-7.87 (m, 3H), 7.73 (d, IH, J=7.7 Hz), 7.13 (t, 2H, 8.8 Hz); MS(ESI+) m/z 234 (M+H)+.

The synthetic route of 21190-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/60613; (2007); 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. 913839-73-3, name is 2-(6-(Trifluoromethyl)pyridin-3-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows. name: 2-(6-(Trifluoromethyl)pyridin-3-yl)acetic acid

56C. Preparation of N’-(5-bromo-4-(4-chlorophenyl)pyridin-2-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetohydrazide; To a suspension of 5-bromo-4-(4-chlorophenyl)-2-hydrazinylpyridine (37 mg, 0.12 mmol), 2-(6-(trifluoromethyl)pyridin-3-yl)acetic acid (26 mg, 0.12 mmol) and bromotripyrrolidinophosphonium hexafluorophosphate (PyBop, 70 mg, 0.13 mmol) in CH3CN (1.0 mL) was added (i-Pr)2EtN (32 mg, 0.25 mmol) at 20° C. The reaction mixture was stirred at 20° C. under argon for 15 h, then concentrated in vacuo. The residue was dissolved in EtOAc (15 mL). The organic solution was successively washed with saturated aqueous NaHCO3 (5 mL) and saturated aqueous NaCl (5 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified using reverse phase preparative HPLC (Conditions: Phemomenex Luna 5mu C18 30.x.75 mm; Eluted with 0percent to 100percent B, 10 min gradient, 100percent B hold for 2 min, (A=90percent H2O, 10percent CH3CN, 0.1percent trifluoroacetic acid and B=10percent H2O, 90percent CH3CN, 0.1percent trifluoroacetic acid); Flow rate at 40 mL/min, UV detection at 220 nm), followed by basification with 1N aqueous NaOH to pH 12 and extraction with EtOAc to afford 54 mg (92percent) of the title compound as a white solid. LC/MS (method B): retention time=1.91 min, [M+H]+=487.0.

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, 913839-73-3, 2-(6-(Trifluoromethyl)pyridin-3-yl)acetic acid.

Reference:
Patent; Sun, Chongqing; Huang, Yanting; Sitkoff, Doree F.; Lee, Taekyu; Ewing, William; US2006/287324; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 122306-01-8, 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.122306-01-8, name is (6-Bromopyridin-3-yl)methanol, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

Reference Example 16; 2-bromo-5-(chloromethyl)pyridine hydrochloride 2-Bromo-5-(hydroxymethyl)pyridine (2.64 g) was dissolved in THF (70 mL) and, after ice-cooling, thionyl chloride (5.11 mL) was added dropwise. The reaction mixture was stirred at the same temperature for 30 min, and concentrated. The obtained residue was washed with diethyl ether to give the title compound (2.65 g) as yellow crystals.1H-NMR (CDCl3) delta: 4.55 (2H, s), 7.52 (1H, d), 7.63 (1H, dd), 8.40 (1H, d).

Statistics shows that 122306-01-8 is playing an increasingly important role. we look forward to future research findings about (6-Bromopyridin-3-yl)methanol.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/270359; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75279-39-9, 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. 75279-39-9, name is N-(4-Aminopyridin-2-yl)acetamide. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 9-(4-methoxybenzyl)-2-(6-methylpyridin-2-yl)-6-phenoxy-9H-Purine (500 mg, 1.181 mmol) and 3-fluoropyridin-4-amine (529 mg, 4.72 mmol) in DMF (5 mL) was added a 60% dispersion of sodium hydride (236 mg, 5.90 mmol) in mineral oil and the mixture was stirred for 3 h. LCMS indicated completion of reaction. The reaction mixture was quenched carefully with water (25 mL) and allowed to stand for two hours. The resulting brown precipitate was filtered and washed with water followed by petroleum ether and dried to afford N-(3-fluoropyridin-4-yl)-9-(4-methoxybenzyl)-2-(6-methylpyridin-2-yl)-9H-purin-6-amine (400 mg, 0.634 mmol, 53.7 % yield) as a brown solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75279-39-9, N-(4-Aminopyridin-2-yl)acetamide, and friends who are interested can also refer to it.

Reference:
Article; Harikrishnan, Lalgudi S.; Warrier, Jayakumar; Tebben, Andrew J.; Tonukunuru, Gopikishan; Madduri, Sudhakara R.; Baligar, Vishweshwaraiah; Mannoori, Raju; Seshadri, Balaji; Rahaman, Hasibur; Arunachalam; Dikundwar, Amol G.; Fink, Brian E.; Fargnoli, Joseph; Fereshteh, Mark; Fan, Yi; Lippy, Jonathan; Ho, Ching-Ping; Wautlet, Barri; Sheriff, Steven; Ruzanov, Max; Borzilleri, Robert M.; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 1026 – 1034;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 33252-28-7 ,Some common heterocyclic compound, 33252-28-7, molecular formula is C6H3ClN2, 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.

2.0 g (14.4 mmol) 6-chloronicotinic acid nitrile are stirred in 7.0 ml (7.3 g, 144.4 mmol) hydrazine hydrate at a bath temperature of 100 C. for 15 min. The reaction mixture, cooled to RT, is diluted with water and stirred at RT for 30 min. The precipitate which has separated out is filtered off, the residue on the filter is washed with water and the crystals are dried in air overnight and recrystallized from ethyl acetate.Yield: 1.5 g (80% of th.)LC-MS (Method 1): Rt=0.51 min; MS (ESIpos): m/z=135 [M+H]+;1H-NMR (400 MHz, DMSO-d6)=8.56 (s, 1H), 8.35 (s, 1H), 7.73 (d, 1H), 6.75 (m, 1H), 4.42 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33252-28-7, its application will become more common.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/305085; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem