Category: pyridine-derivatives

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. 142337-95-9, name is 3-Bromo-5-ethylpyridine. A new synthetic method of this compound is introduced below., Formula: C7H8BrN

Commercially available 3-acetyl-5- bromopyridine (6.53 g, 32.8 mmol), solid NaOH (13.1 g, 326 mmol), and hydrazine hydrate (13 mL) was heated in di ethylene glycol (25 mL) at 140 0C for 4 hours. The reaction mixture was partitioned between ether and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give an oil. This was dissolved in tetrahydrofuran (40 mL) and cooled to 0 0C. Isopropylmagnesiumchloride (20 mL, 2.0 M in THF) was syringed in and the reaction mixture was stirred for 2 hours at room temperature. N,N-dimethylformamide (7 mL) in tetrahydrofuran (15 mL) was added and stirring was continued for. an additional hour. The solution was quenched with 2 N HCl to pH of 3 then partitioned between ethyl acetate and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give 3- ethyl-5-formylpyridine (0.78 g, 18%) as a solid. 1H NMR (DMSO-^6): delta 10.1 (s, IH), 8.91 (s, IH), 8.71 (s, IH), 8.00 (s, IH), 2.75 (q, 2H), 1.31 (t, 3H). MS m/z calculated for (M + H)+ 152, found 152.

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, 142337-95-9, 3-Bromo-5-ethylpyridine.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 145934-89-0, 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 145934-89-0, name is 2-Chloro-5-hydrazinylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step B: 1 -(6-fluoropyridin-3-yl)-3-pyridin-3-yl-5-ftrifiuoromethyl)-4,5-dihydro-l H-pgammarazol-5-olA solution of 2-chloro-5-hydrazinopyridine (136 mg, 0.95 mmol) and acetic acid (0.29 mL, 5,00 mmol) in ethanol (2 mL) is added to a stirred solution of (lZ)-45454-trifluoro-l-pyridin-3-ylbut-l- ene-l,3,3-triol (160 mg, 0,68 mmol) in ethanol (2 mL) in a pressure tube. The reaction mixture is heated at 90 0C (oil bath temp) overnight, cooled and concentrated. The residue was purified by silica gel chromatography (2% to 10% MeOH in CH2Cl2). LRMS: m/z found: 343.5 (M+l).

According to the analysis of related databases, 145934-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/151800; (2009); 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. 54864-83-4, name is 6-Chloro-N,N-dimethylnicotinamide, the common compound, a new synthetic route is introduced below. Computed Properties of C8H9ClN2O

1 -(4-/Lery-Butylphenyl)-6-chloro-2-ethoxycarbonylmethyl-5-hydroxyindole-3- carboxylic acid ethyl ester (120 mg, 0.26 mmol, see step (b) above), 6-chloro-Lambda^7V- dimethylriicotinamide (72 mg, 0.39 mmol), K2CO3 (181 mg, 1.31 mmol) and DMF (3 mL) was heated at 115 0C for 96 h and filtered through Celite. The solids were washed with EtOAc and the combined filtrates concentrated and purified by chromatography to give the sub-title compound. Yield 48 mg (78%).

The synthetic route of 54864-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2006/77366; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13958-93-5, 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 13958-93-5 as follows.

Preparation of 3,5-Dichloro-N-[4-(2-hydroxy-ethyl)-benzyl]-isonicotinamide: Using the EDCI coupling general procedure F: Reaction of 2-(4-Aminomethyl-phenyl)-ethanol (306 mg, 2.03 mmol), 3,5-dichloroisonicotinic acid (385 mg, 2.03 mmol), 1-hydroxybenzotriazole (301 mg, 2.22 mmol), 4-methyl morpholine (0.50 mL, 4.45 mmol), and EDCI (426 mg, 2.22 mmol) in anhydrous DMF (5 mL) overnight at room temperature and overnight at 40 C. followed by column chromatography on silica gel (2:2:96 MeOH-NH4OH-CH2Cl2) gave the title compound (291 mg, 44%) as a white foam.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13958-93-5, its application will become more common.

Reference:
Patent; Bridger, Gary; Skerlj, Renato; Kaller, Al; Harwig, Curtis; Bogucki, David; Wilson, Trevor R.; Crawford, Jason; McEachern, Ernest J.; Atsma, Bem; Nan, Siqiao; Zhou, Yuanxi; Schols, Dominique; Smith, Christopher Dennis; Di Fluri, Maria Rosaria; US2002/147192; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 113293-70-2, 2,6-Dichloroisonicotinaldehyde, 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, 113293-70-2, blongs to pyridine-derivatives compound. Application In Synthesis of 2,6-Dichloroisonicotinaldehyde

To a solution of commercially available 2,6-dichloropyridine-4-carbaldehyde (0.3 g, 1.7 mmol) in CH2CI2 (34 ml.) under N2 at -78 0C is added DAST (0.67 ml_, 5.1 mmol). The reaction is allowed to warm to room temperature, stirred 1 h, and poured into cold water. The separated aqueous layer is extracted with fresh CH2CI2 The combined organic layers are dried (Na2SO4), concentrated, and purified by flash chromatography (10% EtOAc/heptanes) to yield an orange oil: 1H NMR (400 MHz, CDCI3) delta ppm 6.60 (t, J=55.1 Hz, 1 H), 7.40 (s, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113293-70-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); 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, Safety of 5,6-Dichloropicolinic acid, blongs to pyridine-derivatives compound. Safety of 5,6-Dichloropicolinic acid

A four-neck 500 milliliter (mL) round bottomed flask was fitted with a thermocouple/J-KEM controller, mechanical stirrer, condenser that vented to a knock-out pot then to a 12% sodium hydroxide (NaOH) scrubber and a stopper. To the vessel was added concentrated sulfuric acid (H2SO4; 27.0 grams (g), 0.28 moles (mol)) and sulfolane (28.9 g). This mixture was warmed to 130 C. and then the solid trichloromethyl-pyridine (70.2 g, 0.26 mol) was added in portions over ca. 1 hour (h). Vigorous degassing to the caustic trap was observed. After the addition was complete, the mixture was stirred at 130 C. for 2 h and then allowed to cool to room temperature with stirring overnight resulting in a thick taffy. The mixture was warmed to 70 C., and a sample was taken for high performance liquid chromatography (HPLC) analysis which indicated a very clean conversion to the corresponding carboxylic acid. To the pot at 70 C. was carefully added isopropyl alcohol (IPA; 83.2 g, 1.39 mol) in portions over about 45 minutes (min) Initially there was vigorous degassing to the NaOH/caustic trap. After the addition was complete, the clear brown solution was stirred at 70 C. for 1 h. The 70 C. solution was added to crushed ice (361 g) with swirling of the flask. At the end of the addition, there was very little ice in the slurry. The slurry was cooled in the refrigerator for 1 h, and the solid was collected via filtration. The cake was washed with IPA/water (31 g/31 g) and then water (65 g). The material was allowed to air dry in a hood to a constant weight providing the product as a light beige solid (55 g, ca. 89%): HPLC purity was 98.5%; EIMS (70 eV) m/z 235, 233 (M+, 1%, 2%), 220, 218, 194, 192, 176, 174, 149, 147 (100%); 1H NMR (400 MHz, CDCl3) 7.98, 7.91 (ABq, J=8.0 Hz, 2H), 5.30 (m, 1H), 1.41 (d, J=4.0 Hz, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88912-24-7, 5,6-Dichloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Allen, Laura; Sanford, Melanie; Lee, Shin Hee; Bland, Douglas; Cheng, Yang; Roth, Gary; Muhuhi, Joseck M.; US2015/141654; (2015); 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. 1206775-52-1, name is 5-Bromo-6-methoxypicolinaldehyde, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-6-methoxypicolinaldehyde

(1) (5R) -5 – [(1,3- benzothiazol-2-ylsulfonyl) methyl] pyrrolidin-2-one (2.80 g), in tetrahydrofuran (170 mL) solution of lithium chloride (824 mg), argon gas atmosphere, at -78 , toluene solution (0.5M, 39mL) of potassium hexamethyldisilazide, and the mixture was stirred at the same temperature for 1 hour. Tetrahydrofuran (10 mL) solution was added to thereto 5-bromo-6-methoxy-pyridine-2-carbaldehyde (1.75g), and stirred at the same temperature for 30 minutes. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, after filtration, concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform: ethyl acetate = 50: 50) to give, (5R) -5 – [(Z) -2- (5- bromo-6-methoxy-pyridin-2-yl) ethenyl] pyrrolidin-2-one (900 mg) as a pale yellow oily substance.

The synthetic route of 1206775-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 189230-41-9, 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 189230-41-9 as follows.

b) Preparation of intermediate 34A mixture of intermediate 33 (1.8 g, 9.57 mmol) and 4-fluoro-benzoic acid (1.34 g, 9.57 mmol) in polyphosphoric acid (25 g) was stirred and heated for 1 h at 180 0C. The r.m. was cooled to r.t, and water was added. The resulting sol. was neutralized with K2Ctheta3, and the resulting precipitate was filtered off and washed with water. Yield: 1 g of crude intermediate 34, which was used as such in the next reaction step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; BISCHOFF, Francois Paul; ZHUANG, Wei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; MACDONALD, Gregor, James; OEHLRICH, Daniel; WO2010/94647; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1403899-44-4 ,Some common heterocyclic compound, 1403899-44-4, molecular formula is C9H11ClN2, 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.

Alternative procedure: Potassium teit-butoxide (600 mg, 5.36 mmol) was added to a stirred solution of 6-chloro-3,3-dimethyl-2,3-dihydro-1 H-pyrrolo[3,2-c]pyridine (800 mg, 4.38 mmol) in anhydrous THF (15 mL) and the mixture was stirred at room temperature for 10 minutes. Asolution of di-teit-butyl dicarbonate (1.07 g, 4.89 mmol) in anhydrous THF (15 mL) was added and the mixture was stirred at room temperature overnight. The organic solvent was removed in vacuo, the aqueous residues were diluted with water (100 mL) and extracted with EtOAc (2 x 200 mL). The organic layers were combined and the solvent was removed in vacuo to afford the title compound (1.19g, 96%), NMR data consistent with those previouslyobtained.

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. 1403899-44-4, 6-Chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; MILLEMAGGI, Alessia; HOWARD, Steven; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; WO2014/60768; (2014); 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. 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid, molecular formula is C8H8N2O2, 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. Formula: C8H8N2O2

EDC (231 mg, 1.2 mmol) was added to a solution of (E)-3- (6-AMINO-PYRIDIN-3- yl) acrylic acid (164 mg, 1.0 mmol), methyl- (3-methyl-benzofuran-2-ylmethyl) amine (193 mg, 1.1 mmol), HOBTNo.H2O (149 mg, 1.1 mmol) and DIPEA (525 PL, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2X20 mL). The oraganic layer was washed with brine (2 x 30 mL), dried and evaporated. Flash chromatography (silica 1-3% MEOH in CH2Cl2) of the residue furnished pure free base which was dissolved in CH2C12 (10 mL). After addition OF HCL (1.5 mL, 1M in ether), the solvents were evaporated, washed with ether and dried to afford the title compound (195 mg, 54%). 1H NMR (300 MHz, DMSO-d6) 8 8.36 (m, 3H), 7.50 (m, 3H), 7.25 (m, 3H), 7.02 (m, 1H), 4.98 and 4.79 (rotamers, 2s, 2H), 3.17 and 2.92 (rotamers, 2s, 3H), 2.26 (s, 3H). MS (ESI) nile 322 (M+H) +.

With the rapid development of chemical substances, we look forward to future research findings about 167837-43-6.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem