Pyridine-derivatives

Synthetic Route of 1452-63-7 , The common heterocyclic compound, 1452-63-7, name is Picolinohydrazide, molecular formula is C6H7N3O, 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.

General procedure: In a typical reaction, brevenal was dissolved in DMF and the hydrazide (2 eq) was added, followed by addition of a catalytic amount of tungstophosphoric acid. The reaction mixture was heated at 60 C for 4 h. The solvents were evaporated under vacuum and the residue was taken up in methanol. The mixture was filtered through a 0.2 mum nylon filter and subjected to purification by HPLC. Desired products were positively identified by HRMS mass spectrometry and NMR. Spectroscopic data collected for all compounds can be found in the supplementary data document.

The synthetic route of 1452-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Goodman, Allan; McCall, Jennifer R.; Jacocks, Henry M.; Thompson, Alysha; Baden, Daniel; Abraham, William M.; Bourdelais, Andrea; Marine Drugs; vol. 12; 4; (2014); p. 1839 – 1858;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1204296-03-6 ,Some common heterocyclic compound, 1204296-03-6, molecular formula is C6H4ClF2N, 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.

2-Chloro-4-(difluoromethyl)pyridine (2.0 g, 12 mmol) and (R)-3-methylbutan-2-amine (4.3 g, 49 mmol) were added to a 30 mL microwave tube. The resultant mixture was stirred while heating at 180 C. for 16 hours and at 200 C. for another 16 hours before cooling to room temperature and concentrating to dryness under reduced pressure to give the crude product, which was purified by FCC (0-10% ethyl acetate/petroleum ether) to afford the title compound as a yellow oil

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1204296-03-6, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; McClure, Kelly; Tanis, Virginia M.; Fennema, Elizabeth G.; Lebsack, Alec D.; Martin, Connor L.; Venkatesan, Hariharan; Xue, Xiaohua; Woods, Craig R.; (531 pag.)US2017/313691; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-89-9, 2,3-Dibromopyridine, 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: C5H3Br2N, blongs to pyridine-derivatives compound. Formula: C5H3Br2N

General procedure: 2,4-Dibromopyridine (0.236 g, 1 mmol) and phenol (0.094 g, 1 mmol), CuI (19.0 mg, 0.1 mmol), TMEDA (11.6 mg, 0.1 mmol), and cesium carbonate (0.65 g, 2 mmol) were placed in DMSO (5 mL). The reaction was stirred at 110 C under nitrogen atmosphere for 24 h. When the reaction mixture was cooled, the reaction mixture was filtered. The mixture was dissolved with dichloromethane (25 mL). Then the mixture was washed with brine (3×30 mL). The organic phase was dried over sodium sulfate. After evaporation of the solvent, the mixture was subjected to column chromatography with petroleum ether/ethyl acetate (20:1) as eluent to give pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-89-9, 2,3-Dibromopyridine, and friends who are interested can also refer to it.

Reference:
Article; Zhou, Qizhong; Zhang, Bin; Du, Tieqi; Gu, Haining; Ye, Yuyuan; Jiang, Huajiang; Chen, Rener; Tetrahedron; vol. 69; 1; (2013); p. 327 – 333;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 104830-06-0, 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 104830-06-0, name is 2-Amino-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-Dimethylamino-1-(3-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-4-phenylcyclohexanol 2-Amino-3-iodopyridine (3,108 mg, 14.13 mmol), 4-(dimethylamino)-4-phenyl-1-(prop-1-ynyl)cyclohexanol (4,000 mg, 15.54 mmol), lithium chloride (630 mg, 14.83 mmol) and sodium carbonate (4.49 g, 42.38 mmol) were combined in dimethylformamide (absolute, 60 ml) in an argon atmosphere. The catalyst ([Pd(dppf)Cl2*CH2Cl2], 1,154 mg, 1.41 mmol) was then added. The red solution was heated at 79 C. (oil bath temperature) for 5 h. To bring the reaction to completion, a further 0.3 equivalent of 2-amino-3-iodopyridine (932 mg, 4.24 mmol) and 0.05 equivalent of catalyst (577 mg, 0.71 mmol) were added. Thereafter, the mixture was stirred at 99 C. (oil bath temperature) for a further 2 h. The black reaction mixture was cooled to room temperature and water (50 ml; stirring for 10 min) and methylene chloride (50 ml) were added in succession. The phases were separated (the mixture was filtered over kieselguhr) and the aqueous phase was extracted with methylene chloride (3*20 ml). The combined organic phases were washed with saturated NaCl solution (3*20 ml) and dried over sodium sulfate. After filtration, the volatile constituents were removed completely in vacuo. The residue was absorbed on kieselguhr and separated by chromatography (silica gel [200 g]; chloroform/ethanol [9:1 1,000 ml]). 1,200 mg (3.43 mmol; 22% of the non-polar diastereomer were isolated as a colourless solid.

According to the analysis of related databases, 104830-06-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUNENTHAL GmbH; US2010/9986; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 170886-13-2, 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 170886-13-2, name is 2-(Trifluoromethyl)pyridin-4-ol. This compound has unique chemical properties. The synthetic route is as follows.

An alternative synthetic process is provided: A mixture of 2-(trifluoromethyl)pyridin-4-ol (5 g, 30.7 mmol), 3,4-difluorobenzaldehyde (4.36 g, 30.7 mmol) and potassium carbonate (8.47 g, 61.3 mmol) in Nu,Nu-dimethylformamide (DMF) (30 mL) was sealed and heated under microwave at 110 C for 3 h. Then the reaction mixture was cooled, and concentrated in vacuo. The concentrate was purified via Biotage column (Hexane/EtOAc 100% to 3/1) to afford the title compound (6.4 g, 37.6%) as a white solid. LCMS (ESI): m/z 286 [M + H]+; 1.35 min (ret time)

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 170886-13-2, 2-(Trifluoromethyl)pyridin-4-ol.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; SANG, Yingxia; WAN, Zehong; ZHANG, Qing; WO2014/114694; (2014); 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.97483-77-7, name is 5-Bromopicolinonitrile, molecular formula is C6H3BrN2, molecular weight is 183.01, as common compound, the synthetic route is as follows.Computed Properties of C6H3BrN2

Intermediate 10: 1-(5-Bromopyridin-2-yl)ethanone; See W098/46605; 5-Bromo-2-cyanopyridine (Markevitch, David Y. ; Rapta, Miroslav; Hecker, Scott J. ; Renau, Thomas E. ; Synth. Commun.; 33; 19; 2003; 3285 – 3290) (8 g, 43.7 mmol) was dissolved in dry THF (200 mL) and cooled to – 20C. Methylmagnesium bromide (43.7 mL, 3M) was added drop wise and the temperature was held between -20C and -10C for 3 hours. The reaction mixture was cooled to -40C and concentrated HCl (4.5 mL) in water (15 mL) was added dropwise. It was stirred for 10 minutes at -35C and then poured into a beaker with potassium phosphate buffer (300 mL, 1M, pH 7), under stirring. Ethyl acetate (300 mL) was added and the organic phase was dried over sodium sulfate. Upon concentration at room temperature under reduced pressure to – 50 mL the product crystallized, 2.4 g, mp 112C. The mother liquor was further concentrated and chromatographed on silica gel with dichloromethane/ ethylacetate (100:1) to give another 3.25 g product (65% combined yield). (at)H-NMR (DMSO-d(at)) No.: 2.60 (s, 3H) ; 7.88 (dd, 1H) ; 8.25 (dd, 1H) ; 8.86 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,97483-77-7, 5-Bromopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA UK LIMITED; WO2005/116023; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6200-60-8, Imidazo[1,2-a]pyridine-3-carboxylic 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, Quality Control of Imidazo[1,2-a]pyridine-3-carboxylic acid, blongs to pyridine-derivatives compound. Quality Control of Imidazo[1,2-a]pyridine-3-carboxylic acid

General procedure: To a solution of 2-methyl-3-phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine, Intermediate 1, (150 mg, 0.7 mmol) in dichloromethane (DCM) (5.0 mL) was added HATU (348 mg, 0.91 mmol), followed by DIPEA (0.6 mL, 3.5 mmol) and 1-naphthoic acid (222 mg, 1.3 mmol), and the mixture stirred at room temperature for 1 h. The reaction mixture was diluted with water and the aqueous layer extracted with DCM (*2). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase HPLC (Method A) to afford the title compound as a white solid (94 mg, 36% yield). MS (ESI): mass calcd. for C24H21N3O, 367.1; m/z found, 368.1 [M+H]+. 1H NMR (400 MHz, Methanol-d4) delta 8.12-7.93 (m, 2H), 7.89-7.74 (m, 1H), 7.67-7.35 (m, 9H), 5.20-4.92 (m, 2H), 4.46-4.22 (m, 1H), 4.13-3.98 (m, 0.3H), 3.76 (d, J=54.9 Hz, 3H), 3.52-3.41 (m, 1H), 2.93-2.75 (m, 0.7H), 2.57-2.30 (m, 1H).

The synthetic route of 6200-60-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Chen, Gang; Huang, Chaofeng; Laforteza, Brian Ngo; Ravula, Suchitra; Southgate, Emma Helen; Zhang, Wei; US2020/102303; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1211516-25-4, 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. 1211516-25-4, name is 6-Bromo-5-methylpicolinic acid. A new synthetic method of this compound is introduced below.

3-Chlorophenylboronic acid (CAN 63503-60-6, 0.61 g, 3.9 mmol), 1 , l’-bis(diphenyl- phosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464- 05-4, 53 mg, 0.065 mmol) and potassium carbonate (CAN 584-08-7, 0.54 g, 3.9 mmol) was added to a solution of 6-bromo-5-methyl-pyridine-2-carboxylic acid (0.7 g, 3.2 mmol) in water ( 30 mL). The mixture was stirred at 100°C overnight. The reaction mixture was adjusted to pH = 3 and the mixture was extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated in vacuo to give product (0.55 g, 56.9percent); MS (EI): m/e 248.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211516-25-4, 6-Bromo-5-methylpicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 677728-92-6, 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 677728-92-6 as follows.

A suspension of 6-fluoro-pyridine-3-carbaldehyde (125 mg, 1.0 mmol), N-[3-(3-fluoro-4-hydroxy-phenyl)-2-oxo-oxazolidin-5(S)-ylmethyl]- acetamide (200 mg, 0.746 mmol), K2CO3 (552 mg, 4.0 mmol) in acetonitrile (20 niL) was stirred at 60 C under nitrogen for 15 h. The reaction mixture was diluted with EtOAc, filtered and evaporated. The crude product was purified by flash chromatography (1 : 1 hexane/EtOAc followed by 1 % MeOH in EtOAc) to give the title product as oil (235 mg, 84 %). ESI MS m/z 31 A (M + H+); 1H NMR (400 MHz, CD3OD) delta 9.97 (s, 1 H), 8.60 (d, J= 2.0 Hz, 1 H), 8.29 (dd, J= 8.4, 2.4 Hz, 1 H), 7.70 (dd, J= 12.0, 1.6 Hz, 1 H), 7.33-7.20 (m, 3 H), 4.80-4.78 (m, 1 H), 4.19 (t, J= 9.0 Hz, 1 H), 3.85 (dd, J= 9.6, 6.4 Hz, 1 H), 3.58 (d, J= 4.8 Hz, 2 H), 1.97 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; WO2009/120789; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62068-78-4, 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.62068-78-4, name is 2,6-Dichloronicotinamide, molecular formula is C6H4Cl2N2O, molecular weight is 191.02, as common compound, the synthetic route is as follows.

To a stuffed solution of 2,6-dichloro-nicotinamide (500.00 mg; 2.62 mmol; 1.00 eq.) in DMF (5.00 ml; 10.00 V) was added 3-(4-hydroxy-phenoxy)-benzonitrile (670.16 mg; 3.14 mmol; 1.20 eq.) and cesium carbonate (1722.97 mg; 5.24 mmol; 2.00 eq.) at RT. The resulting reaction mixture was stirred for 5h. The reaction completion was confirmed by TLC. After completion of the reaction, the reaction mixture was quenched by the addition of water (20 mL). The solid was collected by filtration and dried under vacuum. The solid was further triturated with acetonitrile (25 mL) and filtered and dried under vacuum to afford 6-chloro-2-[4-(3-cyano- phenoxy)-phenoxy]-nicotinamide (800.00 mg; 83.6 %; off white solid). HPLC: 98.06% purity. MS: m/z = 364.0 [M+H].

The chemical industry reduces the impact on the environment during synthesis 62068-78-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GMBH; QIU, Hui; CALDWELL, Richard D.; NEAGU, Constantin; MOCHALKIN, Igor; LIU-BUJALSKI, Lesley; JONES, Reinaldo; TATE, Devon; JOHNSON, Theresa L.; GARDBERG, Anna; WO2015/61247; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem