Pyridine-derivatives

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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H2BrClF3N

Step C. (1 S, 1 aS,6aR)-4-((5-(6-chloro-4-(trifluoromethyl)pyridin-3-yl)-2-fluorobenzyl)oxy)- l, la,6,6a-tetrahvdrocyclopropara1indene-l -carboxylic acid, ethyl ester 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine (974 mg, 3.74 mmol) was added to a solution of (l S,laS,6aR)-4-((2-fluoro-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)benzyl)oxy)-l, la,6,6a-tetrahydrocyclopropa[a]indene-l -carboxylic acid, ethyl ester (1.583 g, 3.5 mmol) in DME (20 ml) under N2, followed by potassium carbonate (2.43 g, 17.58 mmol) and l,l’-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex (35 mg, 0.043 mmol). The mixture was heated at 90C overnight. It was poured into saturated NH4CI solution and extracted with EtOAc (lx). The organic phase was washed with brine, dried (MgS04), filtered and the solvent evaporated. The residue was purified on silica gel using hexane and to give the title compound. MS m/e: (M+H)+ 506, 508.

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, 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); 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.951625-93-7, name is Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7ClN2O2, molecular weight is 210.62, as common compound, the synthetic route is as follows.SDS of cas: 951625-93-7

A suspension of 1 equivalent of compound 15 and 10 equivalents of phenyl hydrazine was heated to 90 C. for 16 hours. Water was added to the reaction mixture at room temperature and decanted to remove the excess phenyl hydrazine. The crude reaction mixture was dissolved in MeOH and 0.1 N NaOH (2:1, 0.033 M) and stirred for 3.5 hours before concentrating to dryness. Purification by column chromatography afforded the title compound 16 as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 6.43-6.72 (m, 1H) 7.04-7.28 (m, 1H) 7.37-7.56 (m, 4H) 7.84-8.13 (m, 2H) 8.33-8.55 (m, 1H) 11.99 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,951625-93-7, Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Helicon Therapeutics, Inc.; US2012/95016; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 944900-06-5, 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.944900-06-5, name is 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, molecular formula is C7H3ClF3NO, molecular weight is 209.55, as common compound, the synthetic route is as follows.

A mixture of 2-chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde 8 (19.0 g, 90.8 mmol), Ti(OEt)4 (41.4 g, 182 mmol), and (S)-(-)-tert-butylsulfinamide (11.2 g, 92.6 mmol) in THF (200 mL) was stirred at reflux for 5 h. The cooled reaction mixture was concentrated, and dissolved in AcOEt (500 mL). The resulting suspension was filtered through a Celite pad, and the filtrate was concentrated and purified by column chromatography (hexane/AcOEt = 4:1) to provide the imine (28.9 g, 99%) as a light yellow solid. 1H NMR (CDCl3) delta: 9.00 (1H, s), 8.53 (1H, d, J = 7.8 Hz), 7.73 (1H, d, J = 7.8 Hz), 1.29 (9H, s). A mixture of the imine (28.9 g, 90.0 mmol), allyl bromide (55.9 g, 0.46 mol), and indium (42.5 g, 0.37 mol) was vigorously stirred in saturated NaBr aq at room temperature for 21 h. After addition of saturated NaHCO3 aq (500 mL), the reaction mixture was extracted with AcOEt (250 mL * 3). The organic layers were filtered through a Celite pad, and dried (Na2SO4), concentrated and purified by column chromatography (hexane/AcOEt = 1:4 with 5% of Et3N) to provide 12 as a colorless solid (30.7 g, 94%). 1H NMR (CDCl3) delta: 7.95 (1H, d, J = 7.8 Hz), 7.64 (1H, d, J = 7.8 Hz), 5.79-5.68 (1H, m), 5.24 (2H, t, J = 14.1 Hz), 5.03-4.99 (1H, m), 3.78 (1H, s), 2.79-2.73 (1H, m), 2.51-2.43 (1H, m), 1.24 (9H, s).

The chemical industry reduces the impact on the environment during synthesis 944900-06-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Matsufuji, Tetsuyoshi; Shimada, Kousei; Kobayashi, Shozo; Ichikawa, Masanori; Kawamura, Asuka; Fujimoto, Teppei; Arita, Tsuyoshi; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Sogawa, Yoshitaka; Nagai, Yoko; Yoshida, Kazuhiro; Abe, Yasuyuki; Kimura, Takako; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 89 – 104;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 188577-68-6, 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.188577-68-6, name is 4,5-Dichloropyridin-2-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.

INTERMEDIATE 2 4,5-Dichloro- V-nitropyridine-2-amine 4,5-Dichloropyridin-2-amine (INTERMEDIATE 1, 45.2 g, 283.0 mmol) was added to 270 mL of ice cold cone. H2SO4, in small portions over ca 20 min. When dissolved, cone. HNO3 (22 g) was added dropwise and the mixture was stirred at ca 5 C for 3.5 h. LCMS indicated total conversion to expected product. The cold mixture was poured on crushed ice/water mixture (3 L), stirred for ca 5 min and then filtered. The solid was collected and slurried in ice cold water (500 mL) and filtered. The procedure was repeated until neutral pH. When semi dry on the filter, the solid was dissolved in EtOAc (ca. 3 L) , washed with brine (ca. 100 mL) and the organic layer was dried with Na2S04, filtered, and evaporated to furnish 46.2 g (78%) of 97% pure title product as beige-orange solid. 1H NMR (600 MHz, CD3OD) delta ppm 8.47 (s, 1 H) 8.08 (s, 1 H). MS: (ESI+) m/z 208, 210, 212 [M+H]+, di-chlorine isotopic pattern. INTERMEDIATE 3 4,5-Dichloro-3-nitropyridine-2-amine 4,5-Dichloro-N-nitropyridin-2-amine (INTERMEDIATE 2, 20.0 g, 96.2 mmol) was added to 200 mL of cone. H2S04 at room temperature. After stirring at 40 C for 2.5 h the mixture was cooled to below room temperature and poured onto crushed ice (2 L) while stirring. After the ice had melted, the volume was adjusted to ca. 2 L with ice cold water and the yellow precipitate was collected by filtration and washed with ice cold water until neutral pH (3 x 250 mL). The solid was allowed to semi-dry on the filter and was then dissolved in EtOAc (ca. 800 mL). The organic phase was washed with 0.25 M NaOH (3×30 mL), water (3×15 mL) and brine (15 mL), dried (Na2S04), filtered and the solvent evaporated to furnish 11.7 g (59%) of 99% pure title product as yellow solid. 1H NMR (600 MHz, CD3OD) delta ppm 8.26 (s, 1 H). MS: (ESI+) m/z 208, 210, 212 [M+H]+ chlorine isotopic pattern.

Statistics shows that 188577-68-6 is playing an increasingly important role. we look forward to future research findings about 4,5-Dichloropyridin-2-amine.

Reference:
Patent; KANCERA AB; MELLSTEDT, Hakan; BYSTROeM, Styrbjoern; VAGBERG, Jan; OLSSON, Elisabeth; (274 pag.)WO2016/124553; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75806-86-9, Adding some certain compound to certain chemical reactions, such as: 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine,molecular formula is C5H2BrClN2O2, 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 75806-86-9.

Example 121 : 5-Chloro-3-(4-chloro-3- (trifluoromethyl)phenylsulfonamido)picolinic acid; [00525] Step 1 : A dry 250 mL flask was charged with 2-bromo-5-chloro-3- nitropyridine (24 g, 10 mmol), CuCN (19 g, 20 mmol) and DMF (100 mL). The resultant mixture was stirred at 110 C for 2 h and then concentrated under reduced pressure. Water (100 mL) was added and the aqueous layer was extracted with EtOAc (250 mL X 3). The combined organic layer was washed with brine, dried (MgSO4), and evaporated in vacuo to afford a light yellow solid (15 g) which was used directly for the next step.

According to the analysis of related databases, 75806-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1095823-39-4, Adding some certain compound to certain chemical reactions, such as: 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine,molecular formula is C6H4ClF3N2, 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 1095823-39-4.

Synthesis of Compound A.7. A 20 mL vial was charged with compound A.5 (191.8 mg, 0.0006561 mol), methylene chloride (3.0 mL), a 2.0 M solution of oxalyl chloride in methylene chloride (390 muL) and DMF (10.0 muL, 0.000129 mol). The reaction mixture was stirred for 15 minutes at RT, then concentrated in vacuo and the resultant residue was taken up in acetonitrile (3.0 mL). To this solution was added a solution of compound A.6 (129 mg, 0.000656 mol) and pyridine (0.5 mL, 0.006 mol) in acetonitrile (1.5 mL). The reaction mixture was stirred at RT overnight. The solvent was removed under reduced pressure, and the residue was purified by combiflash (0-30% EtOAc/CH2Cl2) to give compound A.7 in 49% yield. MS: m/z 471 [M+1]+.

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. 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, 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, COA of Formula: C6H5ClN2O2, blongs to pyridine-derivatives compound. COA of Formula: C6H5ClN2O2

To a stirred solution of 55 (5 g, 29 mmol) in EtOH (20 mL) and cone HC1 (20 mL) was added Fe powder (16.2 g, 289 mmole) in small portions at RT over 30 min. The resulting reaction mixture was stirred at RT for an additional 30 min. The solvent was removed in vacuo and water was added to the residue which was then neutralized with NaHC03 and diluted with EtOAc. The reaction mixture was filtered through Celite and washed with EtOAc. The filtrate was transferred to a separatory funnel and the phases separated. The organic layer was washed with water and brine, dried over Na2S0 and concentrated to afford 56 (4.1 g, 99 %) as a yellow solid.

The synthetic route of 22280-60-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; XU, Wei; (170 pag.)WO2017/4609; (2017); 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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine, molecular formula is C6H4Cl2N2O2, 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: 2,6-Dichloro-4-methyl-3-nitropyridine

Cyclopropylmethylamine (8.4 mmol, 0.72 mL, ) was added drop-wise to a solution of 3-nitro-2,6- dichloropyridine (-4.8 mmol, 1.32 g at -75% purity) in THF (10 mL) . The resulting solution was stirred at room temperature for 18 hours. Additional (1272) cyclopropylmethylamine (2.7 mmol, 0.23 mL) was added and the reaction mixture was stirred for 18 hours. The yellow suspension was diluted with ethyl acetate and the solution was washed with saturated sodium hydrogen carbonate solution, dried ( gS04) and evaporated to afford the crude title compound as yellow oil (1.35 g) which was used without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 60010-03-9.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 867279-13-8, 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. 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. A new synthetic method of this compound is introduced below.

To a solution of 4-bromo-2-chloro-5-methylpyridine (0.15 g, 0.73 mmol) in DCM (5 ml) was added 77% mCPBA (0.33 g, 1.45 mmol). The resulting mixture was stirred at rt for 3 days. EtOAc was added followed by 1 : 1 mixture of Na2SO3 and Na2CO3 solutions. The resulting mixture was stirred vigorously for 0.5 hour and the organic phase was separated. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with aq. ‘Na2C03 solution and brine, dried with Na2S04, filtered and evaporated yielding 0.13 g of 4-bromo-2-chloro-5-methylpyridine 1 -oxide. 1H NMR (CDCi3) delta: 8.20-8.23 (m, 1 1 1), 7.66 (s, 1-Iota), 2.31-2.34 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); 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. 884495-00-5, name is 4-Bromo-5-fluoro-2-methoxypyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 884495-00-5

A solution of 4-bromo-5-fluoro-2-methoxypyridine (1.0 g, 4.8 mmol) in THF (15 mL) was cooled to -78 C and n-butyllithium (2.2 mL, 5.5 mmol, 2.5 M in THF) was added drop-wise. The resulting mixture was stirred at -78 C for 10 min and a solution of ethyl 4-oxocyclohexanecarboxylate (1.2 g, 7.3 mmol) in THF (5 mL) was added drop-wise with stirring. The resulting solution was stirred for 2 h at -78 C, poured into 100 mL of saturated, aq. H4CI and extracted with ethyl acetate (3 x 100 mL). The separated organic layers were combined, dried over Na2S04 and concentrated. The residue obtained was purified on silica gel with ethyl acetate/petroleum ether (0-20%) to give compound 25a. Mass Spectrum (LCMS, ESI pos.): Calcd. For C15H20FNO4: 298.1 [M+H]+; found: 297.9.

The synthetic route of 884495-00-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; LANTER, James C.; MEEGALLA, Sanath K.; PLAYER, Mark R.; (275 pag.)WO2018/81047; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem