Category: pyridine-derivatives

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 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

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

Related Products of 849068-61-7, 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 849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 1; Methyl 5-bromo-l/7-pyrrolo [2,3-/>] pyridine-3-carboxylate; A solution of 5-bromo-l//-pyrrolo[2,3-6]pyridine (0.200 g, 1.01 mmol; described in: Mazeas,D. et al, Heterocycles 1999, 50, 1065-1080) in dichloromethane (12 mL) was added to asuspension of aluminum chloride (0.704 g, 5.28 mmol) in dichloromethane (5 mL) under anatmosphere of nitrogen. The resulting mixture was stirred at room temperature for 40 min togive a brownish solution. Trichloroacetyl chloride (0.56 mL, 5.0 mmol) was added and themixture was stirred at room temperature for 17 h. Methanol (10 mL) was added and thesolvent was evaporated in vacuo. The residue was treated with aqueous potassium hydroxide(3 M, 10 mL) and methanol (5 mL) and heated at 60 C for 1 h and 15 min. The mixture wasallowed to cool to room temperature and the pH was adjusted to 1-2 using aqueoushydrochloric acid (2 M). The aqueous phase was extracted with ethyl acetate, dried oversodium sulfate, and the solvent was evaporated to give a brown residue. Acetyl chloride (10mL) was added dropwise to cooled methanol (0 C, 20 mL). The resulting solution was addedto a solution of the brown residue in methanol (10 mL) at room temperature, and the resultingmixture was heated at reflux for 3 h. The mixture was allowed to cool to room temperatureand the solvent was evaporated to give a yellow solid. The crude product was purified on asilica gel column using a gradient, ethyl acetate/heptane mixture (10, 20, 30,40, 50% ethylacetate), as the eluent to give 0.165 g (64% yield) of the title compound as a pale pink solid:’H NMR (DMSO-d6, 300 MHz) 5 12.80 (br s, 1 H), 8.41 (s, 2 H), 8.30 (d, J= 3.0 Hz, 1 H),3.83 (s, 3 H); 13C NMR (DMSO-d6, 75 MHz) 6 163.9, 147.0, 144.1, 134.5,130.5, 119.6,113.1, 105.0, 51.1; MS (ES) m/z 255 and 257 (M++l).

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 849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; WO2006/1754; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 76006-11-6, 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.76006-11-6, name is 7-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Pyrazolopyridine 6 (0.44 g, 2.9 mmol) was dissolvedin dry methanol (50 mL) and N-iodosuccinimide (1.0 g,4.4 mmol) was added in portions. The mixture was stirred atroom temperature for 2h. Then, the solvent was removedunder reduced pressure and the residue was extracted withethyl acetate. The combined organic extracts were washedwith aqueous sodium thiosulfate (10% w/v) solution, thendried over sodium sulfate, filtered and concentrated. Thecrude product was purified by column chromatography (silicagel) using a mixture of cyclohexane/ethyl acetate (6/4,v/v) as the eluent to provide pure 7 as a yellow solid, in 99% yield. mp 252-3 C (EtOAc). 1H NMR (600 MHz, DMSO-d6) 7.50 (d, 1H, H-4, J = 5.5Hz), 8.08 (d, 1H, H-5, J =5.5Hz). HR-MS (ESI) m/z: calcd for C6H4ClIN3, [M1+H]+ =279.9133, found 279.9128. Anal. Calcd for C6H3ClIN3: C,25.79; H, 1.08; N, 15.04. Found: C, 25.91; H, 1.13; N, 14.88.

Statistics shows that 76006-11-6 is playing an increasingly important role. we look forward to future research findings about 7-Chloro-1H-pyrazolo[3,4-c]pyridine.

Reference:
Article; Gavriil, Efthymios-Spyridon; Lougiakis, Nikolaos; Pouli, Nicole; Marakos, Panagiotis; Skaltsounis, Alexios-Leandros; Nam, Sangkil; Jove, Richard; Horne, David; Gioti, Katerina; Pratsinis, Harris; Kletsas, Dimitris; Tenta, Roxane; Medicinal Chemistry; vol. 13; 4; (2017); p. 365 – 374;,
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. 184368-74-9, name is 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C12H19NO4

To a solution of 1-tert-butyl 4-methyl 3,6-dihydro-2H-pyridine-l,4-dicarboxylate (500 mg, 2.07 mmol) in toluene (2.5 mL) was added tetrabutylammoniumbromide (33 mg, 0.10 mmol) under N2, then [bromo(difluoro)methyl]-trimethyl-silane (842 mg, 4.14 mmol) was added drop-wise under N2. The reaction mixture was heated at 110 C and stirred for 16 h in a sealed tube. The residue was filtered and concentrated under reduced pressure to provide the title compound (700 mg) as a brown oil, which was used in the next step without further purification. LC-MS: m/z = 192.1 [M+H]+.

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, 184368-74-9, 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate.

Reference:
Patent; DENALI THERAPEUTICS INC.; DE VICENTE FIDALGO, Javier; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; FRANCINI, Cinzia Maria; HALE, Christopher R.H.; HU, Cheng; LESLIE, Colin Philip; OSIPOV, Maksim; SERRA, Elena; SWEENEY, Zachary K.; THOTTUMKARA, Arun; (226 pag.)WO2018/213632; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 67058-77-9, Adding some certain compound to certain chemical reactions, such as: 67058-77-9, name is 3-Nitro-1H-pyrrolo[2,3-c]pyridine,molecular formula is C7H5N3O2, 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 67058-77-9.

To a solution of 3-nitro-1H-pyrrolo[2,3-c]pyridine (200 mg, 1.23 mmol) in MeOH (20 mL) was added 10% Pd/C (130 mg, 0.12 mmol). After stirred at balloon hydrogen atmosphere for 2 hrs, the mixture was filtered. The filtrate was evaporated in vacuum to give 1H- pyrrolo[2,3-c]pyridin-3-amineas a crude product which was used for next step without further purification.

According to the analysis of related databases, 67058-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); 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.98273-79-1, name is Methyl 3-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Quality Control of Methyl 3-chloroisonicotinate

A solution of 1-(bromomethyl)-4-(methylsulfanyl)benzene (prepared according to D. D. M. Wayner, D. R. Arnold, Can J. Chem., 1984, 62, 1164) (2.54 g, 11.7 mmol) in THF (10 mL) was added dropwise to a slurry of Riecke Zinc in THF (22.8 mL of a commercial suspension [5g Zn/100 mL], 17.5 mmol) under nitrogen. During this time the temperature rose steadily to 35C. After allowing the black slurry to cool to room temperature over 30 min bis(triphenylphosphine)nickel (II) chloride (762 mg, 1.17 mmol) was added followed by a solution of methyl 3-chloroisonicotinate (prepared according to J. Epsztajn, M. W. Plotka, A. Grabowska, Synth. Commun., 1997, 27, 1075) (1.0 g, 5.83 mmol) in THF (10 mL), dropwise, taking care to keep the temperature below 30C. After the addition was complete the reaction was allowed to cool to room temperature over 1 h before being quenched by the addition of sat. NH4Cl (aq) (20 mL) while cooling with an ice bath. The mixture was filtered through Celite ), washing well with EtOAc (3 x 20 mL), the organic layer was separated, dried (MgS04) and evaporated to give a brown oil. The residue was purified by column chromatography [SiO2; EtOAc:pentane, 1:3 increasing polarity to EtOAc:pentane, 1:1 and then to (EtOAc:MeOH:NH40H, 95:5:0.5):pentane, 1:1] to give the title compound as an orange oil; & delta H (CDCl3, 400 MHz) 2.43 (3H, s), 3.82 (3H, s), 4.30 (2H, s), 7.05 (2H, d), 7.18 (2H, d), 7.67 (1H, br), 8.59 (2H, br); MS m/z (TS+) 274 (MH+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Limited; Pfizer Inc.; WO2004/16593; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256561-65-5, 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. 1256561-65-5, name is 3-(Bromomethyl)-5-fluoropyridine hydrobromide. A new synthetic method of this compound is introduced below.

A mixture of 3-(bromomethyl)-5-fluoropyridine hydrobromide (3.4 mmol), 6-methyl- 2-sulfanylpyrimidin-4-ol (370 mg, 2.6 mmol), and triethylamine (1.7 mL, 12.0 mmol) in absolute ethanol (40 mL) was stirred at room temperature overnight. The solid material was removed by filtration. The filtrate was recovered, evaporated, co- evaporated with EtOAc (20 mL), and then dried in vacuo. The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (1 x 20 mL) and diethyl ether (2 x 20 mL), and then dried in vacuo, affording the 2-{[(5-fluoropyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (200 mg, 23% yield); 1H NMR (400 MHz, OMS0-d6): delta 2.21 (s, 3H), 4.41 (s, 2H), 6.02 (s (br), IH), 7. 80 (m, IH), 8.05 (dd, IH, / = 2.0 Hz, 7.6 Hz), 8.46 (d, IH, J = 2.7 Hz), 8.54 (t, IH, J = 1.6 Hz); M+ 252. The product was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256561-65-5, its application will become more common.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); 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 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1196152-34-7

[00177] A solution of 1-methylpiperidine-4-carboxylic acid (1 eq, 0.49 mmol) in thionyl chloride (2 ml_) was stirred under nitrogen atmosphere at RT for 1 h. The reaction was concentrated in vacuo under nitrogen to give a pale yellow solid which was dissolved in DCM (1.5 ml_) and cooled to 0 C. Then pyridine (2.5 eq, 0.1 ml_) and 2-bromo-6-methoxy-pyridin-4- amine (0.8 eq, 0.39 mmol) were added. The mixture was stirred at 0C for 5 mins then a RT for 1 h. The compound was extracted with dichloromethane, washed with water, brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The compound was then purified by reverse phase preparative HPLC-MS to afford A/-(2-bromo-6-methoxy-4-pyridyl)-1- methyl-piperidine-4-carboxamide (90 mg, 56%) as a white solid.

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

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; RABBITTS, Terrence; QUEVEDO, Camilo; CRUZ, Abimael; PHILIPS, Simon; FALLON, Philip Spencer; DUNN, Jonathan Neil; FREEM, Joshua Robert; LEE, Lydia Yuen-Wah; TRAORE, Tenin; WILLIAMS, Sophie Caroline; (219 pag.)WO2019/145718; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem