Pyridine-derivatives

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 86873-60-1, name is 5-Chloro-2-picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 86873-60-1

A mixture of 5-chloro-2-pyridinecarboxylic acid (1.0 g, 6.35 mmol) and cone. H2SO4 (0.1 ml) was heated in EtOH (10 ml) at 80 0C for 16 hours. After cooling and concentrating at reduced pressure, the residue was dissolved in EtOAc (50 ml), washed with saturated NaHCO3 (25 ml) and brine (25 ml), dried (MgSO4), filtered and re-concentrated at reduced pressure giving the title compound (990 mg, 84%).LCMS data: Calculated MH+ (186); Found 98% (MH+) m/z 186, Rt = 1.13 min. NMR data: 1H NMR (250 MHz, CDCl3) delta ppm 8.63 – 8.76 (1 H, m), 8.10 (1 H, d, J=8.4 Hz), 7.82 (1 H, dd, J=8.5, 2.4 Hz), 4.49 (2 H, q, J=7.2 Hz), 1.45 (3 H, t, J=7.2 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 86873-60-1.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; WO2009/135842; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15827-84-6, 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 15827-84-6, name is 4-Aminonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Example 11 4-Amino-3-(5-morpholin-4-yl-1H-benzimidazol-2-yl)-1,6-naphthyridin-2(1H)-one LiHMDS (3.3 eq) was added to ethyl (5-morpholin-4-yl-1H-benzimidazol-2-yl)acetate (1.0 eq) and 4-aminopyridine-3-carbonitrile (see J. Chem. Soc. 1967, p1558-1564; 1.0 eq) in THF at 0 C. The reaction was stirred overnight. The resulting mixture was quenched with an aqueous saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. The crude material was washed successively with CH2Cl2 and MeOH, and then was purified by reverse phase HPLC to provide the desired product. LC/MS m/z 363.2 (MH+), Rt 1.55 minutes.

According to the analysis of related databases, 15827-84-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Renhowe, Paul A.; Machajewski, Timothy; Shafer, Cynthia M.; Wernette-Hammond, Mary Ellen; Pecchi, Sabina; US2002/103230; (2002); 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. 67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-Bromo-2-chloro-3-nitropyridine

In a vial are introduced 1 ml of MeOH and 50 8 rng (2.21 mmol) of Na. After dissolution of the metal, the solution was added to a suspension of 5-bromo-2-chloro-3-nrtropyridine (Matrix, Columbia, USA, 500 mg, 2.11 mmol) in MeOH (2 ml) The reaction mixture is stirred for 1 h at O6C and for 15 h at rt, then concentrated and quenched with water. The precipitate was filtered, washed with water (2x) and dried under vacuum to give the title compound as a pale yellow solid (HPLC. tR 3.06 mm (Method A)

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, 67443-38-3, 5-Bromo-2-chloro-3-nitropyridine.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15128-82-2 ,Some common heterocyclic compound, 15128-82-2, molecular formula is C5H4N2O3, 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.

Preparation 3; Preparation of 3-Oxo-3.4-dihydro-2H-pyrido[3,2-bi? ,41oxazine-6-carboxaldehyde; a) 2-Bromo-5-hydroxy-6-nitropyridine; 3-Hydroxy-2-nitropyridine (20 g, 0.143 mole) was dissolved in methanol (400 ml_) and a solution of 25% sodium methoxide in methanol (33 ml_, 0.13 mole) was added at room temperature. The mixture was stirred for 30 min, then was cooled to 0 0C, and bromine (7.2 ml_, 0.14 mole) was added slowly. The reaction was stirred at 0 0C for 30 min, then was quenched with glacial AcOH (2.5 ml_). The solvent was removed in vacuo to afford material (30 g, 96%), which was used without further purification. EPO MS (ES) m/z219.0 (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,15128-82-2, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/81264; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1215387-58-8, 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 1215387-58-8 as follows.

To a solution of 5-bromo-lH-pyrrolo[2,3-c]pyridine (0.9 g, 4.57 mmol, 1.0 eq), Zn(CN)2 (0.32 g, 2.74 mmol, 0.6 eq), Pd(PPh3)4 (234.5 mg, 0.457 mmol, 0.1 eq) in DMF (11.0 mL) at 147 C for 3.5 h under microwave irridiation. After the reaction was complete, it was extracted with EA. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (EA/PE = 1/1, v/v) to provide lH-pyrrolo[2,3-c]pyridine-5-carbonitrile (0.567 g, 78%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1215387-58-8, its application will become more common.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2016-99-1, 2,6-Dibromoisonicotinic 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, Application In Synthesis of 2,6-Dibromoisonicotinic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 2,6-Dibromoisonicotinic acid

To a stirred solution of commercially available 2,6-dibromoisonicotinic acid (3 g, 10.7 mmol) in THF (77 ml) was added N,N-diisopropylethylamine (3.45 g, 4.66 ml, 26.7 mmol), commercially available 2-methylpropan-2-amine (956 mg, 1.37 ml, 12.8 mmol) and TBTU (4.46 g, 13.9 mmol). The reaction mixture was allowed to stir for 17h at room temperature, filtered, evaporated and purified by flash chromatography on silica gel [heptane/ ethyl acetate (0-50%)] to yield 2,6-dibromo-N-tert-butylpyridine-4-carboxamide (3.28 g, 91%) as an off-white solid, MS (ISP) m/z = 337.0 [(M+H)+], mp 148C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2016-99-1, 2,6-Dibromoisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HOENER, Marius; WICHMANN, Juergen; (65 pag.)WO2017/9274; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15862-37-0, 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 15862-37-0, name is 2,5-Dibromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: 5-Bromo-2-(4-chloro-3,5-difluorophenyl)-3-nitropyridine A 24/40-100 mL round bottom flask was charged with 2,5-dibromo-3-nitropyridine (2.00 g, 7.09 mmol) and 2-(4-chloro-3 ,5 -difluorophenyl)-4,4,5 ,5 -tetramethyl-1,3,2-dioxaborolane (1.95 g, 7.09 mmol). The mixture was diluted with THF(30 mL), and PdC12(dppf) (0.0520 g, 0.07 10 mmol) was added followed by aq. potassiumphosphate tribasic, (2.0 M, 7.09 mL, 14.2 mmol). The vial was sealed and degassed usingultra pure argon and sonication for 2 mm. The vial was placed in an oil bath preheated to65 C. After 35 mm, the reaction mixture was concentrated under reduced pressure,diluted with ethyl acetate and a brine solution, and filtered through a pad of Celite. The contents of the flask were transferred into a separatory funnel, and the organic was washed with brine (3X) and then back extracted with ethyl acetate. The combined organics were dried with magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (40 g ISCO RediSep Rf, loaded inlwith:DCM and dried, initial waste: 0 mL, fraction size: 9 mL 13x 100 mm, and eluted with dichloromethane in hexanes 0% [102 mL], 0-20% [150 mL], 20% [501 mL], 20-50% [252 mL], 50% [150 mL]). The fractions were collected to give 1.59 g (64%). ?H NMR (400MHz, CDC13) oe 8.94 (d, J=2.0 Hz, 1H), 8.37 (d, J=2.3 Hz, 1H), 7.23-7.16 (m, 2H). Mass found 350 [M+H].

According to the analysis of related databases, 15862-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59237-53-5, 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 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A flask was charged with methyl-6-chloro-5-nitronicotinate (2.00 g, 9.23 mmol), PdC12(PPh3)2 (324.00 mg, 461.70 jimol) and Cul (87.90 mg, 461.70 jimol). The system was evacuated and filled thrice with N2 before addition of TEA (44 mL) and DMF (88 mL) and the resulting solution was degassed with N2 for 10 mm. Thencyclopropylacetylene (1 .56 mL, 18.49 mmol) was added and the reaction mixture was stirred at rt for 18 h. Then, the reaction mixture was concentrated. The residue was purified by column chromatography on silica gel (Irregular SiOH 15-40 jim, 80 g, dry loading on celite®, mobile phase: heptane/DCM, gradient from 50:50 to 0:100). The fractions containing the product were combined and concentrated under vacuum to give1.3 g of intermediate 293 (58percent yield, brown solid).

According to the analysis of related databases, 59237-53-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18605-16-8 , The common heterocyclic compound, 18605-16-8, name is 6-Fluoro-2-methyl-3-nitropyridine, molecular formula is C6H5FN2O2, 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.

N-(2-Methyl-6-morpholin-4-ylpyridin-3-yl)guanidine; Step 1 : 4-(6-Methyl-5-nitropyridin-2-yl) morpholine; To a solution of 2-fluoro-5-nitro-6-picoline (3.0 g, 19.2 mmol) in DMSO (26 mL) were added morpholine (3.35 mL, 38.4 mmol) and potassium carbonate (6.64 g, 48.0 mmol). The reaction mixture was allowed to stir overnight, at 70C. The reaction mixture was then partitioned between EtOAc (40 mL) and water (40 mL). The organic solution was separated and the aqueous solution was extracted with EtOAc (2 x 40 mL). The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated to give 4-(6-methyl-5-nitropyridin-2-yl) morpholine (4.0 g, 99%), as a muddy green solid. LCMS (FA): Rt = 1.59 min, m/? = 224.0 (M+H).

The synthetic route of 18605-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu, T.; DUFFEY, Matthew, O.; ELDER, Amy, M.; GUO, Jianping; LI, Gang; REYNOLDS, Dominic; SOUCY, Francois; VOS, Tricia, J.; WO2010/65134; (2010); 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. 101066-61-9, name is 2-Chloroisonicotinaldehyde. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4ClNO

To a solution of 2-chloroisonicotinaidehyde (230 mg, 1.60 mmoi) in DCM (3 mL) was added DAST (773 mg, 4,80 rnrnol) at 0C under N2 and the mixture stirred at 0C for lh. Saturated aq. NaHCO3 was added and the mixture extracted with EtOAc (30 rnL x 3). The combined organic layers were dried over MgSO4, filtered, the filtrate concentrated in vacuo and the crude product purified by chromatography on silica (50% EtOAc in petroleum ether) to givethe title compound as an oil. LRMS mlz (M+H) 164.1 found, 164.1 required.

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, 101066-61-9, 2-Chloroisonicotinaldehyde.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem