Category: pyridine-derivatives

Application of 18699-87-1, 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.18699-87-1, name is 2-Methyl-3-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

INTERMEDIATE 13 Ethyl 2Z)-2-hydroxy-3-(3-nitropyridin-2-yl)acrylate Sodium metal (400 mg, [17.] 4 mmol) was added portionwise to [ETOH] (50 ml), followed by diethyl oxalate (2.4 [ML,] 17.4 mmol), and stirred at r. t. for 5 min. 2-Methyl-3- nitropyridine [(2. 00] g, 14.6 mmol) was added, giving a deep purple solution that changed over time to red-orange. After stirring for 3 days at r. t. a red precipitate had formed which was collected by filtration and washed with ether (4 x 20 [ML).] The solid residue was suspended in water and the suspension acidified to pH 4 with AcOH. The resulting orange precipitate was collected by filtration, washed with ethanol (10 [ML)] and dried in vacuo to give the title compound (1.17 g, [34%).] [6H] [(CDC13)] 8. [77-8.] 75 [(1H,] m), [8.] [54-8.] 50 [(1H,] m), 7.47-7. 43 (2H, m), 4.48 (2H, q, [J 7.] 1 Hz), 1.49 (3H, t, J7. 1 Hz). LCMS [(ES] RT 3.32 minutes, 239 [(MI]

The chemical industry reduces the impact on the environment during synthesis 18699-87-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CELLTECH R & D LIMITED; WO2004/31188; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59146-67-7, Adding some certain compound to certain chemical reactions, such as: 59146-67-7, name is 5,6-Dimethylpicolinonitrile,molecular formula is C8H8N2, 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 59146-67-7.

5,6-Dimethylpicolinic acid: 5,6-dimethylpicolinonitrile (example 91b) was refluxed in concentrated HCl (15 mL) overnight. The solvent was evaporated and the solid residue was co-evaporated several times with EtOH. Drying provided 453 mg of 5,6-Dimethylpicolinic acid (80%) as a white solid. MS (M+H, 152.1).

According to the analysis of related databases, 59146-67-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tachdjian, Catherine; Patron, Andrew P.; Adamski-Werner, Sara L.; Bakir, Farid; Chen, Qing; Darmohusodo, Vincent; Hobson, Stephen Terrence; Li, Xiaodong; Qi, Ming; Rogers, Daniel Harry; Rinnova, Marketa; Servant, Guy; Tang, Xiao-Qing; Zoller, Mark; Wallace, David; Xing, Amy; Gubernator, Klaus; US2005/84506; (2005); 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., Product Details of 63237-88-7

Compound 5 was reported previously.30 For this study, 5 wasre synthesized using a modified synthesis as follows: To a solution of pyrazolo[1,5-a]pyridine-2-carboxylic acid (150 mg, 0.93 mmol)and 4 (230 mg, 0.93 mmol) in anhydrous DMF (5 mL) was added DIPEA (0.33 mL, 1.86 mmol) and HATU (372 mg, 0.98 mmol). After stirring the reaction mixture at room temperature for 16 h the solvent was removed under reduced pressure. The crude mixture was suspended in aqueous 5% NaHCO3 solution and extracted with ethyl acetate (3). The combined organic phases were washed with water and brine and were dried (MgSO4). After removal of solvents under reduced pressure the crude material was purified by flash chromatography (CH2Cl2/MeOH/NH3 aq., 20:1:0.01) to give5 (314 mg, 86%) as a colorless solid. 1H NMR (600 MHz, CDCl3) d8.38-8.34 (m, 1H), 7.61-7.51 (m, 1H), 7.29 (br s, J = 5.2 Hz, 1H),7.18-7.12 (m, 2H), 7.09-7.04 (m, 2H), 6.94 (dd, J = 8.0, 1.4 Hz,1H), 6.88-6.81 (m, 2H), 3.58-3.50 (m, 2H), 2.98-2.87 (m, 4H),2.63 (br s, 4H), 2.51-2.45 (m, 2H), 1.76-1.63 (m, 4H); 13C NMR(150 MHz, CDCl3) d 162.2, 151.5, 148.1, 141.4, 139.0, 128.4,126.4, 123.7, 121.5, 120.0, 119.3, 114.0, 113.6, 98.0, 58.1, 53.9,52.6, 39.1, 27.6, 24.4; ESI-MS m/z 394.2 [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, 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid.

Reference:
Article; Stoessel, Anne; Brox, Regine; Purkayastha, Nirupam; Huebner, Harald; Hocke, Carsten; Prante, Olaf; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3491 – 3499;,
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. 29241-65-4, name is 5-Bromo-2-chloronicotinic acid, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To 0.5 L flask charged with 5-Bromo-2-chloronicotinic acid (25.0 g, 106.4 mmol) in MeOH (250 mL) was added H2SO4 (5 mL). The mixture was heated to 60 C., stirred for 1.5 day. LC-MS indicated full conversion of starting material at this time. The reaction was cooled to RT and the volatile components removed in vacuo. The crude residue was dissolved in EtOAc (300 mL), quenched with sat. aqueous Na(HCO3)2 (200 mL). The organic layer was separated, washed with brine, dried over MgSO4 and concentrated to afford the compound, methyl-5-bromo-2-chloronicotinate, as a while solid (quantitative yield). LC-MS (M+H)=250.1.

The synthetic route of 29241-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Conn, P. Jeffrey; Lindsley, Craig W.; Stauffer, Shaun R.; Manka, Jason; Jacobs, Jon; Zhou, Ya; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Jones, Carrie K.; US2012/172391; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7584-08-9, 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 7584-08-9 as follows.

Dissolved 3,5-dimethylpyridine-4-carbonitrile (1.57 g, 11.88 mmol) in DCM (100 mL). Charged with m-Chloroperbenzoic acid (4.10 g, 23.76 mmol). Stirred at room temperature for 16 hours. Washed the reaction mixture with NaHCO3 (100 mL). Washed organic layer with brine and dried over Na2SO4. Filtered and removed solvent. Purified using normal phase chromatography (0-10% MeOH in DCM) to yield 1.57 g of product; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.48 (s, 6H) 8.01 (s, 2H); LCMS (M/Z): 149.2 (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,7584-08-9, its application will become more common.

Reference:
Patent; Avista Pharma Solutions, Inc.; Speake, Jason D.; (22 pag.)US10239885; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1620-71-9, 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.1620-71-9, name is 5-Methyl-2-(trifluoromethyl)pyridine, molecular formula is C7H6F3N, molecular weight is 161.12, as common compound, the synthetic route is as follows.

Step A: 5-methyl-2-(trifluoromethyl)pyridine 1-oxide 5-methyl-2-trifluoromethyl-pyridine (commercially available, 0.164g) was dissolved in dichloromethane (5 mL). Meta-chloroperoxybenzoic acid (m-CPBA, 0.486 g) was added, and the mixture was stirred 48 hours at ambient (rt) temperature. The solvent was remove under reduce pressure and the crude product was purified by chromatography (solvent: isohexane/diethyl ether 7/3 to diethylether) to give the title compound (120mg) as a white solid. 1H NMR (300MHz, CDCI3): oe (ppm) 8.17 (s, 1H), 7.57 (d,1H), 7.16 (d, 1H), 2.38 (s, 3H) ppm.

Statistics shows that 1620-71-9 is playing an increasingly important role. we look forward to future research findings about 5-Methyl-2-(trifluoromethyl)pyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HALL, Roger Graham; GOEGH, Tibor; JUNG, Pierre Joseph Marcel; EDMUNDS, Andrew; JEANGUENAT, Andre; MUEHLEBACH, Michel; STOLLER, Andre; (98 pag.)WO2016/20286; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-06-6, Methyl 5-bromo-4-methylpicolinate, 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, Product Details of 886365-06-6, blongs to pyridine-derivatives compound. Product Details of 886365-06-6

Into a vial was weighed methyl 5-bromo-4-methylpicolinate (300 mg, 1.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), bis(pinacolato)diboron (364 mg, 1.43 mmol), and potassium acetate (384 mg, 3.91 mmol). Under nitrogen, anhydrous 1,4-dioxane (6.5 mL) was added and the vial was sealed. The reaction mixture was stirred at 120 C. for 18 h. After cooling to rt, under nitrogen, to the reaction vessel was added (+-)-(trans)-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (447 mg, 1.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), and potassium carbonate (540 mg, 3.91 mmol), and water (1.3 mL). The vial was sealed and stirred at 100 C. for 23 h. The reaction mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-85:15) to afford the target compound as a brown solid (126 mg, 21% over 2 steps); 1H NMR (400 MHz, DMSO-d6) delta 10.95 (s, 1H), 9.38 (s, 1H), 8.71 (s, 1H), 8.28 (s, 1H), 8.01 (s, 1H), 7.56 (s, 1H), 7.37 (br s, 2H), 7.29 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H), 3.77 (s, 3H), 2.25-2.16 (m, 2H), 1.90 (s, 3H), 1.43-1.34 (m, 1H), 1.24-1.14 (m, 1H).

The synthetic route of 886365-06-6 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one, 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, Product Details of 92138-35-7, blongs to pyridine-derivatives compound. Product Details of 92138-35-7

100 L jacketed reactor equipped with a temperature probe, nitrogen inlet and reflux condenser was charged with toluene (27.0 L, 30 vol.) and EtOH (5.4 L, 6 vol.) followed by 6-chloro-3-nitropyridin-2(1H)-one (900.0 g, 5.15 mol) and phenyl boronic acid (640.4 g, 5.253 mol). The mixture was stirred at ambient temperature for 15 minutes before a solution of K2CO3 (173.9 g, 11.33 mol) in DI water (5.4 L, 6 vol.) was added. The reaction mixture was degassed with argon for 30 minutes at room temperature. Tetrakis triphenylphosphine palladium (178.2 g, 3 mol %) was added and the solution was heated to 95-100 C. (internal temperature was 77-79 C.) and stirred for 3 hours. After 3 hours HPLC showed 2.8% of starting material and another single impurity (15.3%, 1.17 RRT). The reaction was maintained for 3 hours at same temperature. After 6 hours, there was no progress in the reaction and the mixture was cooled to room temperature, degassed for 30 minutes, and another 5.0 g of tetrakis triphenylphosphine palladium was added and the solution was heated to 95-100 C. Reaction was deemed complete after one hour by HPLC. The reaction mixture was cooled to room temperature, the reaction was diluted with DI water (11.7 L, 13 vol.) followed by EtOAc (18.0 L, 20 vol.) and stirred for 1 hour. The two layers were separated, leaving the solids in aqueous layer. The aqueous layer was extracted with EtOAc (13.5 L, 15 vol.). The combined aqueous layers were neutralized pH to 6.2-6.8 with 3N HCl, when more solids precipitated out, the solids were filtered off, washed with water (2×2.5 L, 5 vol.) and dried under vacuum at 45-50 C. for 48 hours, to furnish 1a (761.1 g, 68.9% yield, 78.0% purity) as yellow solid. The compound was characterized by 1H NMR (DMSO-d6) and MS. (0157) The combined organic (ethyl acetate) layers were extracted with 3N NaOH (15 L), when solids were formed. The organic layer was separated. The aqueous layer was then acidified pH to 5-6 with 3N HCl, when more solids were precipitated out, which were filtered off and washed with DI water (2.0 L) and dried to obtain compound 1a (140.0 g, 12.7%, 93.8% purity, 2nd crop).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; Bates, Craig; Chen, Jian-Xie; Mao, Jianmin; Reed, David P.; US2015/266876; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 103058-87-3, 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 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 1; 4- (5-formgammal-6-methoxypyridin-3-gammal) benzonitrile; A mixture of 5-bromo-2-methoxynicotinaldehyde (2.0 g) synthesized by a known method (Journal of Heterocyclic Chemistry 1985, 22(6), 1583-1592), (4- cyanophenyl) boronic acid (1.36 g) , Pd(PPh3)4 (0.32 g) and potassium carbonate (2.6 g) in THF (20 mL) and water (10 mL) was heated under reflux for 12 hrs. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated under reduced pressure. The obtained residue was crystallized from acetone/ethanol/IPE to give the title compound (0.93 g) as white crystals . melting point: 157C

According to the analysis of related databases, 103058-87-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/89031; (2007); 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.1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.COA of Formula: C6H4ClF3N2

To a solution of S.6 (205 mg, 0.64 mmol) in methylene chloride (4 mL) at RT was added oxalyl chloride (160 muL, 0.0019 mol) followed by the addition of DMF (50 muL) and stirred at RT for 1 hr. Separately a solution of A.6 (132 mg, 0.000672 mol), acetonitrile (2 ml) and pyridine (520 muL, 0.0065 mol) was stirred at RT followed by the addition of chlorotrimethylsilane (100 muL, 0.0008 mol). The acid chloride was concentrated under reduced pressure to a tan solid and redissolved in acetonitrile (2 mL). To the acid chloride solution was added the activated aniline. After 3 hr, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with dilute citric acid (50 mL), aqueous sodium bicarbonate (50 mL) and water. The organic layer was dried over sodium sulfate and concentrated to a residue which was purified by to give compound S.7. LCMS m/z: 498.95 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem