Pyridine-derivatives

Electric Literature of 274-76-0, 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.274-76-0, name is Imidazo[1,2-a]pyridine, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

a) Imidazo [1, 2-a] pyridine-3-carbaldehyde; Imidazo [1, 2-a] pyridine (0.500 g, 4.23 mmol) was dissolved in 1 mL of DMF and phosphorus oxychloride (0.71 g, 4.6 mmol) was added dropwise and the mixture was stirred and checked on LC-MS. After lh the mixture was poured into water and made alkaline with 1M NaOH. The mixture was extracted three times with EtOAc and the combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel with DCM: MeOH 99: 1-96: 4. Yield: 83 mg (13%). ‘H NMR (300 MHz, CDCl3) 6 9.95 (s, 1H), 9.50 (m, 1H), 8.32 (s, 1H), 7.80 (m, 1H), 7.56 (m, 1H), 7.13 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 274-76-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2005/66132; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5444-01-9, 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.5444-01-9, name is 4-Methylnicotinonitrile, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

1M LiHMDS (45mL, 44.794mmol) was added to a solution of 4- methylnicotinonitrile (2.52g, 21.33mmol) in THF (15mL) at -78C and the resulting reaction mass was stirred at -78C for 1 hour. This was followed by the addition of dimethyl carbonate (1.98mL, 23.464mmol) and stirred the resulting reaction mass at – 78C for 1 hour and further at 0C for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was quenched with saturated NH4C1 solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (25% ethyl acetate in hexane) afforded 530 mg of the product (14.10% yield).1H NMR (300 MHz, CDC13): delta 8.9 (s, 1H), 8.79 (d, 1H), 7.4 (d, 1H), 3.9 (s, 2H), 3.79 (s, 3H)

The chemical industry reduces the impact on the environment during synthesis 5444-01-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; MOEBITZ, Henrik; SENGUPTA, Saumitra; WO2012/35078; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88912-24-7, 5,6-Dichloropicolinic acid, 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, 88912-24-7, blongs to pyridine-derivatives compound. Recommanded Product: 88912-24-7

Sodium hydride (CAN 7646-69-7, 60% w/w, 1.05 g, 26 mmol) was added tocyclopropylmethanol (CAN 2516-33-8, 7.5 g) at 0C and the mixture was stirred for 1 h. 5,6-Dichloro-pyridine-2-carboxylic acid (1 g, 5 mmol) was added and the mixture was heated to 95C for 3 h. The solvent was removed under reduced pressure. The residue was diluted with water (10 mL) and adjusted to pH = 3.0 by hydrochloric acid (3 N). The solution was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with water (3 x 30 mL) and brine (2 x 40 mL) and evaporated to dryness to give the crude product (0.35 g, 25%>), which was used in the next step without further purification, MS (EI): m/e = 228.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,88912-24-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58819-88-8, 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 58819-88-8 as follows.

To an oven-dried 40 mL vial was added 6-bromo-2-methoxynicotinaldehyde, dichloromethane (0.5M), and (R)-2-methylpropane-2-sulfmamide (1.0 equiv.) at room temperature. To the vial was then added titanium tetraethoxide (2.0 equiv.). The mixture was stirred overnight before being diluted with sodium bicarbonate solution. The contents of the vial were filtered through celite, and the filtrate was washed once with water and once with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography using hexanes/ethyl acetate gradient to yield (R,E)-N-((6-bromo-2-methoxypyridin-3-yl)methylene)-2-methylpropane-2- sulfmamide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58819-88-8, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (300 pag.)WO2019/204609; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 29681-44-5, Adding some certain compound to certain chemical reactions, such as: 29681-44-5, name is Methyl 5-bromonicotinate,molecular formula is C7H6BrNO2, 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 29681-44-5.

To a solution methyl 5-bromonicotinate (5 g, 23 mmol) in ethanol (40 mL) was added hydrazine hydrate (6 mL, 115 mmol). The reaction mixture was refluxed at 90 C for 4 h. After this time, the reaction mixture was evaporated to dryness and then redissolved in ethyl acetate. The organic layer was washed with water, dried and evaporated to yield 5 -bromonicotinohydrazide (3.4 g, 72 %). LCMS Method T: retention time 0.573 min; [M+l] = 216.0, 218.0.

According to the analysis of related databases, 29681-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JOHNSON, James A.; LLOYD, John; FINLAY, Heather; JIANG, Ji; NEELS, James; DHONDI, Naveen Kumar; GUNAGA, Prashantha; BANERJEE, Abhisek; ADISECHAN, Ashokkumar; WO2011/28741; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 929617-30-1, Adding some certain compound to certain chemical reactions, such as: 929617-30-1, name is 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine,molecular formula is C7H6BrN3, 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 929617-30-1.

To a solution of 5-Bromo-3-methyl-lH-pyrazolo[3,4-c]pyridine from Example 102 (106 mg, 0.5 mmol) in DMF (5 mL) was added Pd(dppf)Cl2 ( 20 mg ), saturated solution of Na2C03 ( 1 mL ) and lH-pyrazol-3-ylboronic acid ( 67 mg, 0.6 mmol ). The mixture was stirred under argon for 16 h at 80 C. After cooling down, the solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE = 1 : 1) to afford 103 (15 mg, 15% ). 1H NMR (500 MHz, MeOD) delta 8.96 (s, 1H), 8.23 (s, 1H), 7.71 (s, 1H), 6.90 (d, J= 1.5, 1H), 2.65 (s, 3H). ESI MS m/z = 200.1 (M+l)

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. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; LEE, Wendy; TSUI, Vickie Hsiao-Wei; WANG, Xiaojing; WEN, Zhaoyang; WO2013/24002; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, 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, 112110-07-3, blongs to pyridine-derivatives compound. Formula: C6H5F3N2

A mixture of Pd2(dba)3 (11 mg, 0.012 mmol) and BrettPhos (13 mg, 0.025 mmol) in l,4-dioxane (1 mL) was stirred at 50 C for 10 min. l-(3-chloro-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (80 mg, 0.25 mmol), 5-(trifluoromethyl)pyridin-3-amine (49 mg, 0.30 mmol) in dioxane (5 mL) and CS2CO3 (248 mg, 0.762 mmol) were added and the resulting mixture was stirred at 100 C for 16 h. A black brown mixture was formed. LCMS (Rt = 0.702 min; MS Calcd: 440.2; MS Found: 440.9 [M+H]+). The reaction mixture was diluted with DCM (10 mL), filtered and concentrated. The residue was purified by prep-HPLC (0.05% NH32O as an additive) and lyophilized to give l-(5-methyl-3-((5- (trifluoromethyl)pyridin-3-yl)amino)-5H-chromeno[4,3-c]pyridin-8-yl)pynOlidin-2-one (25.0 mg, yield: 22%) as a white solid. (1164) NMR (400 MHz, DMSO-r/e) d 1.53 (3H, d, J= 6.8 Hz), 2.00-2.09 (2H, m), 2.52 (2H, overlap with DMSO), 3.83 (2H, t , J= 7.6 Hz), 5.29 (1H, q, J= 6.8 Hz), 6.77 (1H, s), 7.30 (1H, dd, J = 8.4, 2.0 Hz), 7.39 (1H, d, J= 2.0 Hz), 7.91 (1H, d, J= 8.4 Hz), 8.42 (1H, s), 8.74 (1H, s), 9.79 (1H, t, J = 2.0 Hz), 8.94 (1H, d, J= 2.4 Hz), 9.85 (1H, brs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,112110-07-3, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89282-03-1, 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 89282-03-1 as follows.

A reaction mixture containing 3-ethynyl-5-nitro-1 -trityl-1 H-indazole (215 mg, 0.5 mmol), 3-iodo-pyridin-4-ol (132 mg, 0.6 mmol), copper (I) iodide (4.5 mg, 0.025 mmol), PdCI2(PPh3)2 and triethylamine (120 mg, 1.2 mmol) in DMF (3 ml_) was heated at 100 C overnight under argon. After the completion of reaction (shown by TLC), ethyl acetate (50 mL)was added and the reaction mixture was added to water. The organic layer was collected, washed with water, brine and concentrated under vacuum. After purification using silica (7% methanol in dichloromethane), the desired product was obtained (210 mg, 0.4 mmol ) in 80% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89282-03-1, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2008/153858; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 188425-85-6, 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. 188425-85-6, name is 2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide. A new synthetic method of this compound is introduced below.

Add in a 100ml round bottom flask11-bromodecanoic acid 1 g (3.77 mmol),EDCI (0.72 g, 3.77 mmol) and HoBT (0.5 g, 3.77 mmol),Add 40 ml of dichloromethane to react for 15 min.Then, Boscalid {2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide} 1.24 g (3.6 mmol) was added. After 4 h of reaction, 1.5 g of 2-chloro-N-(4-chlorobiphenyl-2-yl)-N-(11-bromoundecyl)nicotinamide was obtained in a yield of 93%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,188425-85-6, its application will become more common.

Reference:
Patent; China Agricultural University; Tan Zhaohai; Wang Jiayao; Liu Xuelian; Tang Dachao; Xiao Yumei; Li Jiaqi; (46 pag.)CN109053801; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1149-24-2 , The common heterocyclic compound, 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, 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.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

The synthetic route of 1149-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem