Category: pyridine-derivatives

Electric Literature of 881-86-7 ,Some common heterocyclic compound, 881-86-7, molecular formula is C9H9NO4, 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.

Step 1. Preparation of (c^)-dimethyl piperidine-2.5-dicarboxylate To dimethyl pyridine-2,5-dicarboxylate (50 g) was added AcOH (500 mL) and catalyst 5percent RI1/AI2O3 (5 g). The reaction mixture was shaked under H2 (100 psi) at 25 oC for 16 h. The catalyst was removed by filtartion. The AcOH was removed under vacuum and the residue was used without furtherpuirification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,881-86-7, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; ALHASSAN, Abdul-Basit; ANAND, Rajan; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; YU, Wensheng; YU, Younong; LIU, Shilan; WU, Hao; YANG, Chundao; (120 pag.)WO2016/109215; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-86-7, 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 153034-86-7, name is 2-Chloro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-chloro-4-iodopyridine (4.943 g, 20.6 mmol) and formic acid(88%, 10 mL) was stirred at 105 C. for 21 h. The excess of formic acid was removed in vacuo, and the mixture was quenched with 2 M aq Na2CO3, extracted with 0H2Cl2, dried over Na2SO4. After the solvent was removed under reduced pressure, the residue was purified by chromatography on silica gel eluted with CH2Cl2/MeOH to afford 1.716 g (38%) of 4-iodopyridin-2(1H)-one as a solid. LC-MS Method 1 tR=0.82 min, m/z=222 (MH+); 1H NMR (400 MHz, (0D3)2SO) delta 7.14 (d, J=6.5 Hz, 1H), 6.87 (s, 1H), 6.49 (d, J=7.0 Hz, 1H).

According to the analysis of related databases, 153034-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Boehringer Ingelheim International GmbH; US2010/331320; (2010); 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.66909-29-3, name is 6-Chloro-5-methylnicotinic acid, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.SDS of cas: 66909-29-3

A solution of e-chloro-delta-methyl-nicotinic acid (13.85 g, 80.75 mmol) in dry ethanol (200 ml_) containing some drops of concentrated H2SO4 is stirred at reflux for 2 days. The solution is cooled to rt, the solvent evaporated, the residue dissolved in EA (200 ml_) and washed with a solution of sat. aq. Na2CO3 (2 x 80 ml_), 1 M aq. KHSO4 (2 x 80 ml_) and brine (50 ml_). The org. phase is dried over MgSO4, filtered and evaporated to give e-chloro-delta-methyl-nicotinic acid ethyl ester (12.65 g) as a solid; LC-MS: tR = 0.92 min; [M+1]+ = 200.10; 1H NMR (CDCI3) delta 1.43 (t, J = 7.0 Hz, 3 H), 2.46 (s, 3 H), 4.43 (q, J = 7.3 Hz, 2 H), 8.16 (m, 1 H), 8.84 (d, J = 2.0 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,66909-29-3, 6-Chloro-5-methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/24905; (2009); A1;,
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 99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

D. lambda/-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)acetamideA mixture of 6-chloro-5-(trifluoromethyl)pyridin-3-amine (2.95 mmol, 0.58 g) and 30% HBr in acetic acid (6 ml) in a sealed tube was heated at 1000C overnight. The crude mixture was poured into ice water, the pH was set to10 with 2N aqueous NaOH and extracted withCHCI3.The solvent was removed under reduced pressure to afford 0.680 g (82% of yield) of the expected product.ESI/MS (m/e, %): 281.96 (100.0%), 283.96 (97.3%).

With the rapid development of chemical substances, we look forward to future research findings about 99368-68-0.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214334-70-9, 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid, molecular formula is C7H6BrNO3, 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.

To a solution of 5-bromo-6-methoxypyridine-2-carboxylic acid (500 mg, 2.15 mmol, 1 eq) in sulfuric acid (10 mL) in ice bath was added HNO3 (5 mL) dropwise. The solution was stirred at 60 C for 16 h. After cooling to rt, the solution was poured into ice/water (20 mL). The solids were collected by filtration to provide 3-amino-5-bromo-6-methoxypyridine-2-carboxylic acid as a light yellow solid (260 mg, 44%). LCMS (ES) [M-l]” m/z 275.0.

According to the analysis of related databases, 1214334-70-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; LI, Zhe; YU, Ming; XU, Qing; ZANCANELLA, Manuel; (246 pag.)WO2019/36377; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-81-9 ,Some common heterocyclic compound, 884494-81-9, molecular formula is C6H5BrFNO, 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.

3,5-Dimethyl-isoxazole-4-sulfonic acid 4-(5-fluoro-2-methoxy-pyridin-3-yl) benzylamide Di-tert-butyl dicarbonate (3.5 g, 16 mmol) and triethylamine (13 ml, 9.4 mmol) were added to a stirred solution of 4-aminomethylphenylboronic acid (3 g, 16 mmol) in tetrahydrofuran (100 ml). The reaction was stirred under reflux for 1 hour, then the solvent evaporated and the residue partitioned between water and ethyl acetate. The organic phase was concentrated under reduced pressure to give tert-butoxycarbonylaminomethyl-4-phenyl-boronic acid (2.67 g, 10.6 mmol) as a white solid. Toluene (16 ml), ethanol (4 ml), 2M sodium carbonate solution and tetrakis(triphenylphosphine) palladium (0) were added to tert-butoxycarbonylaminomethyl-4-phenyl-boronic acid (1.349 g, 5.4 mmol) and 3-bromo-5-fluoro-2-methoxy-pyridine (0.505 g, 2.45 mmol) and the mixture stirred under reflux for 24 h. Water was added and the mixture extracted with ethyl acetate. The organic phase was separated and the solvent evaporated. The residue was purified on silica gel eluting with 3:1 heptane/ethyl acetate to give [4-(5-fluoro-2-methoxy-pyridin-3-yl-benzyl]-carbamic acid-tert-butyl ester as a yellow oil. Trifluoroacetic acid (2 ml, 0.026 mmol) was added to a solution of [4-(5-fluoro-2-methoxy-pyridin-3-yl-benzyl]-carbamic acid-tert-butyl ester (0.8 g, 2.41 mmol) in dichloromethane (4 ml) and the reaction mixture stirred for 2 h. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The organic phase was separated and the solvent evaporated to give 4-(5-fluoro-2-methoxy-pyridin-3-yl)-benzylamine. The title compound was prepared in a similar manner to N-[1-(2-allyl-5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethyl]-3,4-difluoro-benzenesulfonamide (Example 34) using 4-(5-fluoro-2-methoxy-pyridin-3-yl)-benzylamine and 3,5-dimethyl-isoxazole-4-sulfonyl chloride. MS (ESI) m/z: 392 [M+H]+.

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. 884494-81-9, 3-Bromo-5-fluoro-2-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. Organon; Pharmacopeia Drug Discovery Inc.; US2007/149577; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5350-93-6, Adding some certain compound to certain chemical reactions, such as: 5350-93-6, name is 6-Chloropyridin-3-amine,molecular formula is C5H5ClN2, 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 5350-93-6.

To a solution of 3-amino-6-chloropyridine (lOOmg, 0.77mmol) in DCM (3mL) at -78¡ãC was added a solution of tBuOCl (leq, 87muL) in DCM (ImL) via cannula. After 10 min, a solution of thiomethylacetone (leq, 80 uL) in DCM (ImL) was added via cannula. The reaction stirred for 90 min before the addition of a solution OfNEt3 (leq, 108uL) in DCM (ImL). The mixture was warmed to 25¡ãC. After 2 h, the reaction was quenched with water and extracted with DCM (2x). The organic layer was dried over Na2SO4 and concentrated. Purification via flash chromatography eluding with a gradient of 0 to 100percent EtOAc/hexanes provided 5-chloro-2- methyl-3-(methylthio)-lH-pyrrolo[3,2-b]pyridine as a tan solid.1H NMR (500 MHz, CDCl3): delta 6.89 (bs, IH), 7.51 (d, IH), 7.08 (d, IH), 2.59 (s, 3H), 2.36 (s,3H).

According to the analysis of related databases, 5350-93-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/5672; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 71902-33-5, 3,5-Difluoropyridine, 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, 71902-33-5, blongs to pyridine-derivatives compound. name: 3,5-Difluoropyridine

Preparation Example 12 n-Butyl lithium (1.55M hexane solution, 7.5 mL) was added under an argon gas atmosphere at -78C to a mixture of N,N,N’,N’-tetramethylethylenediamine (1.5 g), and diethylether (40 mL), followed by stirring at the same temperature for 30 minutes. A mixture of 3,5-difluoropyridine (1.2 g) and diethylether (10 mL) was slowly added to the reaction mixture, followed by stirring at the same temperature for 2 hours. Iodine (4.0 g) was further added to the reaction mixture, followed by stirring at the same temperature for one hour and cooling to room temperature. The reaction mixture was diluted with water, the formed solid was separated by filtration, and the filtrate was extracted with diethyl ether and washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3,5-difluoro-4-iodopyridine (820 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71902-33-5, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; EP2394988; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1462-86-8, 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.1462-86-8, name is 3-Aminopicolinic acid, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

3-Aminopicolinic acid (145 mg, 1.05 mmol) was carefully added in 3 aliquots to a slurry of UAIH4 (143 mg, 3.78 mmol) in dry tetrahydrofuran (6 ml). The resulting mixture was stirred at 15C overnight. After cooling in an ice bath, the reaction mixture was quenched with careful addition of water (1 ml) dropwise, followed by 15% aqueous NaOH (1 ml), and then water (3 ml). The resulting solid was filtered and washed several times with tetrahydrofuran. The filtrate was concentrated. The residue was purified by flash chromatography on silica gel using 5% CH3OH (NH3) /ethyl acetate as eluent to yield the title compound as a yellow oil. 1 0 mg.MS (electrospray): m/z [M+H]+ = 125

Statistics shows that 1462-86-8 is playing an increasingly important role. we look forward to future research findings about 3-Aminopicolinic acid.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine, molecular formula is C6H7BrN2O, 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: 2-Bromo-6-methoxypyridin-4-amine

In a 50 mL single collar flask 500 mg (2.4 mmol, 1 eq) of 2 bromo-6-methoxy-pyridin-4- ylamine were introduced, to which was added 20 mL of toluene and 586 mg (4.92 mmol, 2 eq) of thionyl chloride, and the mixture heated at reflux for 3 hours. The reaction medium was dry concentrated under vacuum, and the residue was returned to solution in 20 mL of acetonitrile. 325 mg (2.46 mmol, 1 eq) of 2-hydroxy-2-methyl-pentanoic acid was then added at ambient temperature. After 16 hours at ambient temperature, the reaction mixture was heated to 80C for 4 hours, then to 60C for 3 days, and the reaction mixture was then dry concentrated. The residue was dissolved in 50 mL ethyl acetate. The solution was washed twice with 50 mL of an aqueous solution saturated with ammonium chloride, and then twice with 50 mL of water. The organic phase was then dried over magnesium sulphate and then dry concentrated under vacuum. A brown oil was obtained which was purified by chromatography on silica with a 1/1 (v/v)heptane/ethyl acetate mixture as the eluent. A brown solid was then obtained and purified by chromatography on grafted C18 silica with a water / acetonitrile mixture as the eluent (gradient 5 at 100% acetonitrile). 2-Hydroxy-2-methyl-pentanoic acid (2-bromo-6- methoxy-pyridin-4-yl)-amide was obtained in the form of a white solid. Melting point = 122C. NMR (1H, DMSO): 0.9 (t; 3H; J=4 Hz); 1.1 -1.3 (m; 1 H); 1.4 (s; 3H); 1.4-1 .5 (m; 1 H); 1.6 (m; 1 H); 1 .7 (m; 1 H); 3.9 (s; 3H); 5.8 (s; 1 H); 7.4 (d; 1 H; J=1 .4 Hz); 7.8 (d; 1 H; J=1 .4 Hz); 10.2 (s; 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 1196152-34-7.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; POINSARD, Cedric; WO2013/64681; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem