Pyridine-derivatives

Application of 107504-08-5, 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 107504-08-5, name is 5-Fluoro-2-picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

5-fluoro-pyridine-2-carboxylic acid methyl ester2.7 mL Thionylchloride was dropped to 5 g 5-fluor-pyridine-2-carboxylic acid in 50 mL methanol. The reaction was stirred for 2 h at 65C in a sealded micro wave vial. The solvents were removed and the residue was desolved in a mixture of DCM and methanol and filtered over silica gel. The filtrate was evaporated to give 5.9 g of the desired product.Rt: 0.77 (method K). (M+H)+: 156

According to the analysis of related databases, 107504-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WO2013/79460; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 588729-99-1, 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. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, molecular formula is C5H4BrClN2, 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.

In vessel 1, thionyl chloride (110.0 kg) was added into water (430 kg) at Ca. 0C. The mixture was stirred at Ca. 3 C for 7 h before copper(I) chloride (0.27 kg) was added at Ca. 3 C.In vessel 2, 5-bromo-2-chloropyridin-3-amine (28.2 kg, 136 Mol) was mixed with 35% aqueous hydrochloric acid solution (202 kg) at Ca. 5C. A solution of sodium nitrite (8.5-14.1 kg) in water (19.7-25.4 kg) was then added at Ca. -10 C.The solution in Vessel 2 was added to the solution in vessel 1 while maintaining the temperature at Ca. -7C. The reaction mixture was stirred for 2 h at Ca. -2C. The solid product wasisolated by filtration and dried in vacuo at Ca. 23 C for 18 h. 30.9 kg of the title Compound was obtained in 66 %th yield and 84.3 % assay.

According to the analysis of related databases, 588729-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (129 pag.)WO2019/20657; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 823-56-3, 2-Fluoro-3,5-dichloropyridine, 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: C5H2Cl2FN, blongs to pyridine-derivatives compound. Formula: C5H2Cl2FN

Example 11 Preparing 2,3-difluoro-5-chloropyridine by Reacting 2-fluoro-3,5-dichloropyridine Using tetrakis(diethylamino)phosphonium bromide A 500 ml four-necked flask which is equipped with thermometer, anchor stirrer and reflux condenser with bubble counter is charged with 166 g (1 mol) of 2-fluoro-3,5-dichloropyridine, 68.4 g (1.2 mol) of potassium fluoride and 3.99 g (0.01 mol) of tetrakis(diethylamino)phosphonium bromide. The reaction mixture is then heated with stirring to the predetermined reaction temperature and is allowed to react for the time indicated. After the end of the reaction the reaction mixture is cooled and poured into water which is employed in excess, the mixture is subjected to extraction with methylene chloride, and the isolated methylene chloride phase is washed with water, dried and then subjected to fractional distillation under reduced pressure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823-56-3, 2-Fluoro-3,5-dichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Aventis Research & Technologies GmbH & Co.; US6184425; (2001); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1173081-96-3, 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 1173081-96-3 as follows.

Example 38V-[(4,6-Dimethyl-2-oxo-l,2-dihydro-3-pyridinyl)methyl]-l-(l-methylethyl)-6-phenyl- lH-pyrazo -6]pyridine-4-carboxamideIn a 25 mL sealable tube under nitrogen were combined l-(l-methylethyl)-6- phenyl-lH-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.25 mmol) and 3- (aminomethyl)-4,6-dimethyl-2(lH)-pyridinone.HCl (56.3 mg, 0.3 mmol) in DMSO (3 mL). l-hydroxy-7-azabenzotriazole (51 mg, 0.37 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. N-methylmorpholine (0.1 ml, 0.87 mmol) and EDC (72 mg, 0.37 mmol) were added, the vessel was sealed, and the bright yellow mixture was stirred at room temperature for 2 days. Next added 2 mL of water, and the contents were stirred for 10 min. Solids that precipitated were sonicated, and allowed to stand at room temperature for 10 min. The reaction contents were filtered and washed with water. The solid was treated with 2 mL of EtOH, sonicated and heated, and then allowed to cool to room temperature. The contents were filtered, washed with water and dried to afford the title compound (74 mg, 70%) as a white solid. LCMS E-S (M+H) = 416.3. 1H NMR (400 MHz, DMSO-d6) ? ppm 11.58 (s, 1 H), 8.98 (t, J=4.80 Hz, 1 H), 8.38 (s, 1 H), 8.25 – 8.30 (m, 2 H), 8.17 (s, 1 H), 7.49 – 7.59 (m, 3 H), 5.91 (s, 1 H), 5.30 – 5.38 (m, 1 H), 4.42 (d, J=4.80 Hz, 2 H), 2.23 (s, 3 H), 2.13 (s, 3 H), 1.55 (d, J=6.57 Hz, 6 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1173081-96-3, its application will become more common.

Reference:
Patent; GLAX0SMITHKLINE LLC; BURGESS, Joelle, Lorraine; JOHNSON, Neil, W.; KNIGHT, Steven, David; LAFRANCE, Louis, Vincent, III; MILLER, William, H.; NEWLANDER, Kenneth, Allen; ROMERIL, Stuart, Paul; ROUSE, Meagan, B.; SUAREZ, Dominic; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2013/39988; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5470-22-4, 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 5470-22-4, name is 4-Chloropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of (56) 4-(4-benzothiazol-2-yl-phenylamino)-pyridine-2-carbogylic acid methylamide: [Show Image] Step 1: A mixture of methylamine hydrochloride (544 mg, 8.05 mmol) and 4-chloropicolinic acid (296 mg, 2.30 mmol) in DMF (5 mL) was treated with EDC*HCl (661 mg, 3.45 mmol) and DIEA (2.0 mL, 11.5 mmol) at r.t. for 40 h. was continued over night (LCMS: ST179_21h). Reaction mixture was partitioned between aq. satd NaHCO3 (50 mL) and CHCl3 (3 x 35 mL). Combined org. phases were washed with aq. satd NH4Cl (2 x 50 mL) and dried over MgSO4. The organic phase was purified by chromatography on silica gel using petroleum ether/ethyl acetate 2:1 1 to pure ethyl acetate. Product was finally purified by prep. HPLC. Product fraction was again partitioned between satd aq. NaHCO3 (20 mL) and CHCl3 (3 x 30 mL) to remove any formic acid still present from HPLC, and dried over MgSO4. Resulting oil was dried only under reduced pressure, 25 mbar, as product is volatile at high vacuum.

According to the analysis of related databases, 5470-22-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 4SC AG; EP1746096; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 771579-27-2, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Formula: C8H12N2O

[01751 ] The above acid (0.6 g, 2.2mmol) was then dissolved in DMSO (5 mL) and 3-(amino methyl)-4, 6-dimethylpyridin-2(l H)-one (0.67 g, 4.44 mmol) was added. The reaction mixture was stirred at room temperature for 1 5 min before PYBOP ( 1 .7 g, 3.33 mmol) was added and stirring was continued overnight. After completion of the reaction, the reaction mass was poured into ice; extraction was carried out using 10 % MeOH/DCM. The combined organic layers were dried over sodium sulphate and concentrated under reduced pressure to obtain crude material which was then purified by solvent washings giving the title compound (0.45 g, 50%). LCMS:402.20 (M + 1 )+; HPLC: 98.73% ((at) 254 nm) (R,;4.096; Method: Column: YMC ODS-A 150 mm x 4.6 mm x 5 mu; Mobile Phase: A; 0.05% TFA in water/ B; 0.05% TFA in acetonitrile; Inj . Vol: 10 mu, Col. Temp.: 30 C; Flow rate: 1 .4 mL/min.; Gradient: 5% B to 95% B in 8 min, Hold for 1.5 min, 9.51 -12 min 5% B); ‘H NMR (DMSO-<¾, 400 MHz) delta 1 1 .47 (s, 1 H), 8.22 (t, 1 H, J=4.4 Hz), 6.97 (s, 1 H), 6.92 (s, 1 H), 5.85 (s, 1 H), 4.23 (d, 2H, J=4.4 Hz), 3.75-3.79 (m, 1 H), 2.87-2.93 (m,2H), 2.18 (s, 3H), 2.15 (s, 3H), 2.10 (s, 3H), 1 .99 (m, 2H), 1 .58- 1 .69 (m, 4H), 0.77 (t, 3H, J=6.8 Hz). With the rapid development of chemical substances, we look forward to future research findings about 771579-27-2. Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 851759-19-8 ,Some common heterocyclic compound, 851759-19-8, molecular formula is C8H8ClNO2, 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.

To a solution of tert-butyl 2,2-dimethyl-3-oxo-piperazine-1-carboxylate (1.60 g, 7.01 mmol) in DMF (10 mL) is added 60% NaH/mineral (280 mg, 7.00 mmol). The mixture is stirred at rt for 20 mm, till the bubbling subsided. Then to it are added TBAI (70 mg, 0.19 mmol) and tertbutyl 2,2-dimethyl-3-oxo-piperazine-1-carboxylate (1.6 g, 7.1 mmol). The mixture is stirred at rt for lh under nitrogen, LC-MS of the crude shows a littlew conversion. Then the temperature is raised to 60C, stirred for 3h. After cooling to rt, the mixture is neutralized with formic acid, diluted with Et0Ac (80 mL), washed with water and brine consecutively, dried over sodium sulfate, filtered. The filtrate is concentrated to dryness under reduced pressure and the residue is purified on Biotage SNAP 50g silica gel cartridge eluting with Et0Ac/hexanes 0-30% in 2OCV to obtain tert-butyl 4-(5-methoxycarbonyl-6-methyl-2-pyridyl )-2,2-dimethyl-3-oxo-piperazine-1- carboxylate (755 mg, 37%) as a yellowish solid. LC-MS: 378.77 M(+H+), calc. 378.2028. RT: 1.9 mm using Method C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851759-19-8, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LIU, Bingcan; DORICH, Stephane; DE LESELEUC, Mylene; DUPONT-GAUDET, Kristina; JAMES, Clint, Alwyn; VAILLANCOURT, Louis; BEAULIEU, Marc-Andre; STURINO, Claudio; (236 pag.)WO2018/57588; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19524-06-2, Adding some certain compound to certain chemical reactions, such as: 19524-06-2, name is 4-Bromopyridine hydrochloride,molecular formula is C5H5BrClN, 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 19524-06-2.

4-Bromopyridine hydrochloride (3.0 g, 15.4 mmol) was dissolved in water (15 mL). After addition of N-benzylpiperazine (14.8 mL, 85.0 mmol) and 500 mg copper sulfate, the reaction mixture was heated overnight to 140 C. The resulting product was extracted with ether (5?75 mL), dried over sodium sulfate and concentrated. Final purification by column chromatography (dichloromethane/methanol/NH4OH=10/1/0.1) yielded the desired product (2.16 g, 55percent). 1H NMR (300 MHz, d-CDCl3) 2.68 (dd, 4H), 3.45 (dd, 4H), 6.76 (d, 2H), 7.40 (m, 5H), 8.38 (d, 2H).

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. 19524-06-2, 4-Bromopyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Schering Corporation; US2004/106794; (2004); 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. 84249-14-9, name is 2-Amino-4-bromopyridine. A new synthetic method of this compound is introduced below., name: 2-Amino-4-bromopyridine

4-Phenyl-2-pyridinamine Phenylboronic acid (141 mg, 1.156 mmol), 4-bromo-2-pyridinamine (200 mg, 1.156 mmol) and PdCl2(dppf)CH2Cl2 adduct (94 mg, 0.116 mmol) were collected and suspended in 1,2-dimethoxyethane (3 ml) and 1M aq sodium carbonate solution (3.47 ml, 3.47 mmol). The resulting mixture was stirred at 90 C. for 5 hours then it was cooled to r.t. and filtered over a celite pad washing with DCM. The solvent was evaporated (in vacuo) and the crude was purified by silica gel chromatography (Biotage 40M column) and eluding in gradient with 0%-10% MeOHDCM to afford the title compound (195 mg, 1.146 mmol, 99%). 1H NMR (400 MHz, CDCl3): delta 4.49 (dd, 2H), 6.69-6.78 (m, 1H), 6.90 (dd, 1H), 7.39-7.52 (m, 3H), 7.56-7.68 (m, 2H), 8.10-8.17 (m, 1H); UPLC-MS: 0.42 min, 171 [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, 84249-14-9, 2-Amino-4-bromopyridine.

Reference:
Patent; Biagetti, Matteo; Contini, Stefania Anna; Genski, Thorsten; Guery, Sebastien; Leslie, Colin Philip; Mazzali, Angelica; Pizzi, Domenica Antonia; Sabbatini, Fabio Maria; Seri, Catia; US2009/203705; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79055-52-0, 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. 79055-52-0, name is 2,4-Dibromo-6-methylpyridine, molecular formula is C6H5Br2N, 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.

A Mixture of 13.85 g of 2,4-dibromo-6-methyl-pyridine [79055-52-0], 1.80 g of bis(triphenylphosphine) palladium(II)chloride and 0.50 g of copper(I)iodide in 330 ml of triethylamine is treated with 4.30 ml of 3-butin-1-ol [927-74-2] under Ar atmosphere at 0C. The reaction mixture is stirred for 4 hours at room temperature, diluted with water and extracted with tert-butyl methyl ether (2x). The combined organic phases are dried over sodium sulphate and filtered, and the filtrate is concentrated by evaporation. From the residue, the title compound is obtained as beige solid by re-crystallization from hot ethyl acetate-heptane 3:2. Rf = 0.15 (EtOAc-heptane 2:1); Rt = 2.51 (gradient I). Radicals NR1R2:

According to the analysis of related databases, 79055-52-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Speedel Experimenta AG; EP1764099; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem