Category: pyridine-derivatives

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.

Preparation 13: 6-Chloro-3,3-di methyl-2,3-di hydro-pyrrolo[3,2-c] pyridi ne-I -carboxyl ic acid tert-butyl ester Alternative procedure: Potassium tert-butoxide (600 mg, 5.36 mmol) was added to a stirredsolution 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 addedand 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 x200 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 previously obtained.

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; BUCK, Ildiko Maria; DAY, James Edward Harvey; HOWARD, Steven; SAXTY, Gordon; MURRAY, Christopher William; HOPKINS, Anna; WO2014/60767; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6515-09-9, 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. 6515-09-9, name is 2,3,6-Trichloropyridine, molecular formula is C5H2Cl3N, 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.

2, 3, 6-Trichloropyridine (62 mmol, 11.27 g) was dissolved in a mixture of fuming nitric acid (62 mL) and concentrated sulphuric acid (50 mL) and heated at 100C for 12 hours. The mixture was cooled, carefully poured into ice/water then extracted with dichloromethane. The organic extract was dried (MgS04) then concentrated under reduced pressure to give the title compound as pale green oil which solidified on standing (9.65 g, 68%).

According to the analysis of related databases, 6515-09-9, the application of this compound in the production field has become more and more popular.

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

Reference of 116855-03-9, Adding some certain compound to certain chemical reactions, such as: 116855-03-9, name is 3-Bromo-1-methyl-1H-pyrazolo[3,4-b]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 116855-03-9.

3-bromo-1-methyl-pyrazolo[3,4-b]pyridine (100 mg, 0.472 mmol) is dissolved in toluene (5 mL) and tributyl(1-ethoxyvinyl)tin (187 mg, 0.519 mmol) and tetrakis(triphenylphosphine) palladium(0) (54 mg, 0.047 mmol) are added to the solution and the reaction is refluxed for 2 h. Volatiles are evaporated under reduced pressure and the resulting residue is suspended in THE/aqueous 2M HCI 1:1 andstirring is continued for lh. The reaction mixture is basified with Na2CO3 saturated solution, and extracted with ethyl acetate. The organic layer is dried, evaporated and the resulting residue is purified by flash chromatography (eluent 0-100% EtOAc/Cyclohexane) to give the title compound (70 mg, 85 %)UPLC-MS (Method 2): R = 0.78 mmMS (ESI pos): m/z = 176 (M+H)+

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. 116855-03-9, 3-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13269-19-7, 2-Nitropyridin-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, Formula: C5H5N3O2, blongs to pyridine-derivatives compound. Formula: C5H5N3O2

General procedure: A magnetically stirred solution of pyrazole 4 (500 mg, 3.46 mmol) in DMF (7 mL)was treated with KOH (387 mg, 6.90 mmol) and nitroaniline 7a-e, 10 or 13a-b (3equiv., 10.38 mmol) then heated at 100 C for 1 h. The resulting mixture was cooledto room temperature then treated with NH4Cl (100 mL of a saturated aqueoussolution) and extracted with ethyl acetate (3 × 25 mL). The combined organic phaseswere washed with brine (1 × 50 mL) before being dried (MgSO4), filtered andconcentrated under reduced pressure to afford a yellow oil. Subjection of this residueto flash column chromatography (silica, 1:4 ? 1:1 v/v ethyl acetate/n-hexane gradientelution) and concentration of the relevant fractions afforded the target pyrazole 8a-e,11 or 14a-b.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13269-19-7, 2-Nitropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Article; Reekie, Tristan A.; McGregor, Iain S.; Kassiou, Michael; Tetrahedron Letters; vol. 55; 33; (2014); p. 4568 – 4571;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84487-15-0, 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 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

4-Amino-5-nitropicolinonitrile (Compound 64) A solution of 2-bromo-5-nitropyridin-4-amine (135 mg, 0.619 mmol) and copper cyanide (67 mg, 0.743 mmol) in DMA was heated to 200 C. for 1 h using a microwave reactor. The reaction mixture was partitioned between water and EtOAc and filtered over celite. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by combiflash SiO2 chromatography using (0-50% EtOAc-hexanes) to give 4-amino-5-nitropicolinonitrile (70 mg, 69%) as a pale brown solid. 1H-NMR (400 MHz, CD3OD) delta ppm 9.07 (s, 1H), 7.37 (s, 1H); ESI-MS: m/z 164.77 (M+H)+.

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 84487-15-0, 2-Bromo-5-nitropyridin-4-amine.

Reference:
Patent; Stingray Therapeutics, Inc.; Vankayalapati, Hariprasad; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (117 pag.)US2020/39979; (2020); 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. 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H8BrNO2

Into a vial was weighed methyl 5-bromo-4-methylpicolinate (1.00 g, 4.35 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (181 mg, 0.217 mmol), bis(pinacolato)diboron (1.21 g, 4.78 mmol), and potassium acetate (1.28 g, 13.0 mmol). Under nitrogen, anhydrous 1,4-dioxane (11 mL) was added and the vial was sealed. The reaction mixture was stirred at 100 C. for 18 h. After cooling to rt, the reaction mixture was concentrated and the residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10) to afford 756 mg of crude aryl pinacolboranate intermediate (contaminated with pinacolborane by 1H NMR). Combining this intermediate (323 mg, ?1.17 mmol) with (+-)-(1S,2S)-N-(8-(bis(2,4-dimethoxybenzyl)amino)-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (500 mg, 0.777 mmol), chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (32.8 mg, 0.0389 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (18.9 mg, 0.0389 mmol), and potassium phosphate tribasic monohydrate (554 mg, 2.33 mmol) in a vial, tetrahydrofuran (3.9 mL) and water (0.7 mL) were added under nitrogen and the vial was sealed and stirred at 80 C. for 19 h. The reaction mixture still contained starting material and so an equal aliquot of catalyst, ligand and water, as well as potassium phosphate tribasic monohydrate (184 mg, 0.777 mmol) and crude aryl pinacolboranate (215 mg, ?0.77 mmol) were added and stirred at 80 C. for 3 days. The mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10). The crude compound thus obtained was a yellow oil that contained the product according to HPLC-MS.

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, 886365-06-6, Methyl 5-bromo-4-methylpicolinate.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73672-37-4, 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. 73672-37-4, name is Ethyl 2-oxo-2-(pyridin-3-yl)acetate. A new synthetic method of this compound is introduced below.

Reference Example 36 A mixture of ethyl 3-pyridylglyoxylate (6.00 g), hydroxylamine hydrochloride (2.79 g), sodium acetate (4.13 g) and ethanol (80 ml) was heated to reflux for 15 hours. The reaction mixture was concentrated, water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate to obtain ethyl E-2-hydroxyimino-2-(3-pyridyl)-acetate (3.30 g, yield 51%) as colorless crystals. m.p. 172-173 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73672-37-4, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6251926; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1033772-26-7, 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. 1033772-26-7, name is Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, molecular formula is C8H7N3O2, 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.

To a solution of 1 H-pyrazolo[3,4-c]pyridine-5-carboxylic acid, methyl ester (1.5 g, 8.5 mmol) in THF (350 mL) at 0 0C was added LAH (958 mg) in two portions. The reaction was stirred at 0 0C for 1.5 hr, and at rt for 1 hr. The reaction was quenched with con. NaOH at 0 0C, and the solid was filtered off and washed with MeOH. The filtrate was concentrated. Purification by column afforded 1 H-pyrazolo[3,4-c]pyridine-5-methanol (1.23 g, 96%).

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 1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2008/71451; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109306-86-7, 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.109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.

Add 2g of magnesium turnings, one iodine, a small amount of tetrahydrofuran (THF), and a small amount of 2-(2-bromophenyl)pyridine in a 500ml three-necked flask.After the reaction was initiated, 200 ml of a solution of 2-(2-bromophenyl)pyridine (19 g) in tetrahydrofuran (THF) was slowly added dropwise.After refluxing until the magnesium dust disappeared, 15 g of a solution of compound 3 in THF was added dropwise, 100 ml.The reflux reaction was continued for 8 hours, then the temperature was lowered to room temperature, and 2N hydrochloric acid was added to quench the reaction.The solvent was evaporated under reduced pressure, and 300 ml of acetic acid was added to the obtained solid, and the mixture was heated to reflux for 2 hours.The solvent was removed by filtration at room temperature.After the obtained white solid was dissolved in 100 THF, an equal amount of methanol was slowly added.The white solid product was precipitated to 16.3 g, and the yield was 72.6%.

Statistics shows that 109306-86-7 is playing an increasingly important role. we look forward to future research findings about 2-(2-Bromophenyl)pyridine.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Liu Kaipeng; Yang Yan; Yang Dandan; Zhang Hongke; Gao Renxiao; (25 pag.)CN108948030; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72093-04-0, 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. 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, 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.

Under the protection of nitrogen,Add (0.188 mmol) to the reaction flask in turn.[Ir(COD)Cl] 2 (1,5-cyclooctadiene chloride dimer),R-(+)-1,1′-binaphthyl-2,2′-diphenylphosphine (0.188 mmol),150ml of dichloromethane,Stir at room temperature for 20 min,Then add potassium iodide 20.07g (0.0938mol)And 11.96 g (0.0938 mol) of 3-chloro-4-methylpyridine,The reaction flask was placed in a stainless steel autoclave and replaced with hydrogen three times.Finally, the required hydrogen pressure is 200 psi.After reacting for 12 hours at room temperature,Slowly release hydrogen,The reaction system was diluted with 150 mL of dichloromethane.Add 150 mL of saturated sodium carbonate solution, stir for 15 min, and separateOrganic layer,The aqueous layer was extracted with dichloromethane (3×150 mL).The organic layers were combined and dried over Na 2 SO 4 .The solvent was removed to give Compound III 16.84 g.The yield was 82.3%, and the HPLC purity was 99.55%.The ee value is 82%.

According to the analysis of related databases, 72093-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Luoxin Pharmaceutical Group Hengxin Pharmaceutical Co., Ltd.; Shandong Luoxin Pharmaceutical Group Co., Ltd.; Shandong Yuxin Pharmaceutical Co., Ltd.; Song Lili; Meng Fanna; Liu Mingming; (8 pag.)CN108948021; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem