Category: pyridine-derivatives

Application of 189230-41-9, 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. 189230-41-9, name is 2-Bromopyridine-3,4-diamine. A new synthetic method of this compound is introduced below.

A mixture of intermediate 22 (1.8 g, 9.57 mmol) and 4-fluoro-benzoic acid (1.34 g, 9.57 mmol) in polyphosphoric acid (25 g) was stirred and heated at 180 0C for Ih. The r.m. was cooled to r.t, and water was added. The resulting sol. was neutralized with K2CO3, and the resulting precipitate was filtered off and washed with water. Yield: 1 g of crude intermediate 23, which was used as such in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189230-41-9, 2-Bromopyridine-3,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; WU, Tongfei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; OEHLRICH, Daniel; WO2010/89292; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 150114-71-9, 4-Amino-3,6-dichloropicolinic 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, SDS of cas: 150114-71-9, blongs to pyridine-derivatives compound. SDS of cas: 150114-71-9

24. Preparation of Methyl 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylate A solution of 4-amino-3,6-dichloropyridine-2-carboxylic acid (1100 g, 5.31 mol), 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane-bis(tetrafluoroborate) (2100 g, 5.93 mol) in water (6000 mL) was warmed to 65 C. for six hours. After cooling to ambient temperature, the reaction mixture was stirred an additional eighteen hours. The solution was concentrated and the resulting solid washed with 6 N hydrochloric acid (5*1000 mL) and dried to give 4-amino-3, 6-dichloro-5-fluoropyridine-2-carboxylic acid (757 g, 3.53 mol. 58% purity). This crude material was added to methanol (3000 ML) which had been saturated with anhydrous hydrogen chloride and the reaction mixture was warmed to 45 C. for two hours. The solution was added with vigorous stirring to ice water (4000 mL) and the resulting solid collected. The crude ester was dissolved in ethyl acetate (1000 mL) and washed with saturated sodium bicarbonate solution (2*1000 mL), dried, and concentrated. The resulting solid was recrystallized from ethyl acetate/hexanes to give methyl 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylate (402.5 g, 1.67 mol), mp 128-131 C.

The synthetic route of 150114-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Balko, Terry William; Buysse, Ann Marie; Epp, Jeffrey Brian; Fields, Stephen Craig; Lowe, Christian Thomas; Keese, Renee Joan; Richburg III, John Sanders; Ruiz, James Melvin; Weimer, Monte Ray; Green, Renard Antonio; Gast, Roger Eugene; Bryan, Kristy; US2003/114311; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 97004-04-1, Adding some certain compound to certain chemical reactions, such as: 97004-04-1, name is (6-Chloropyridin-3-yl)methanamine,molecular formula is C6H7ClN2, 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 97004-04-1.

The acid 3-(5-carboxyindol-2-yl)indazole and the 5-(aminomethyl)-2-chloropyridine dissolved in 5 ml of CH2Cl2 are introduced into a 30 ml round-bottomed flask. The EDC and the HOBt dissolved in 5 ml of CH2Cl2 are then added at room temperature under nitrogen. The reaction mixture is stirred at room temperature under nitrogen for 24 hours. A sufficient amount of DMF to fully dissolve the reaction medium is added. A further 0.355 mmol of the reagents EDCI and HOBt are then added. The reaction medium is stirred at room temperature for 5 hours and then poured into water and extracted with EtOAc. After drying and concentrating, 268.5 mg of a yellow oil are thus obtained, which product is purified by chromatography on silica (Biotage), eluting with a 99.5/0.5, 98/2, 95/5, 91/10 CH2Cl2/MeOH mixture by volume. 23.9 mg of 3-(5-(N-(2-chloropyrid-5-yl)methyl)carboxamideindol-2-yl)indazole are thus obtained in the form of a beige-coloured powder. 118.6 mg of a mixture are also obtained, which mixture is repurified by chromatography on a column of 60H silica (12 g), eluting with 99/1, 98/2 CH2Cl2/MeOH by volume. Two fractions of comparable purity of 3-(5-(N-(2-chloropyrid-5-yl)methyl)carboxamideindol-2-yl)indazole are thus obtained (41.8 mg and 49.6 mg, respectively) in the form of whitish powders.

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. 97004-04-1, (6-Chloropyridin-3-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aventis Pharma S.A.; US2004/242559; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 905563-79-3 ,Some common heterocyclic compound, 905563-79-3, molecular formula is C7H6ClNO2, 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.

(S)-N- [( 1 Z -(2-Chloro-4-methoxypyridin-3 -yDmethylidene] -2-methylpropane-2- sulfmamide (0640) To a solution of 2-chloro-4-methoxypyridine-3-carbaldehyde (15 g, 87.4 mmol) in THF (180 mL) at 0C were added sequentially 2-methylpropane-2-sulfinamide (11.72 g, 96.7 mmol), tripotassium phosphate (56.0 g, 264 mmol) and dipotassium hydrogen phosphate (46.0 g, 264 mmol). The cooling bath was removed and the resultant suspension was stirred at r.t. for 18 h. The reaction mixture was filtered through celite, – – (0641) washing through with EtOAc. The filtrate was diluted with EtOAc (250 mL) and washed with brine (200 mL), then dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The crude material was purified by flash column chromatography (Si02, 0-50% EtOAc in heptane) to afford the title compound (22.0 g, 94%) as a pale yellow solid. 5H (500 MHz, CDCls) 8.88 (s, 1H), 8.33 (d, J5.8 Hz, 1H), 6.88 (d, J 5.8 Hz, 1H), 3.96 (s, 3H), 1.29 (s, 9H). LCMS Method 1 (ES+) RT 1.51 minutes, 275/277 (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,905563-79-3, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; SANOFI; DELIGNY, Michael Louis Robert; HEER, Jag Paul; (86 pag.)WO2017/167993; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1026796-81-5, Adding some certain compound to certain chemical reactions, such as: 1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide,molecular formula is C7H7BrN2O, 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 1026796-81-5.

Intermediate 46: N-(4-bromopyridin-2-yl)-N-methylacetamide A/-(4-Bromopyridin-2-yl)acetamide (for a preparation see Intermediate 45, 406 mg, 1.888 mmol) was dissolved in DMF and cooled to 0C. Sodium hydride (60 % w/w) (91 mg, 2.266 mmol) was added and the mixture was stirred for 15 minutes, lodomethane (142 muIota, 2.266 mmol) was added at rt and the reaction was stirred for 2 h. Water was added and the product was extracted with diethyl ether (x 4). The combined organics were evaporated to leave a residue which was purified by silica gel column chromatography (50-100 % EtOAc/cyclohexane). Fractions containing product were combined and concentrated in vacuo to give the title compound as a colourless oil (252 mg, 1.100 mmol, 58.3 % yield). LCMS (2 min, High pH): Rt = 0.69 min, MH+ 229/231

According to the analysis of related databases, 1026796-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 56673-34-8, 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 56673-34-8, name is 3-Bromo-6-mercaptopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To MeOH (40 mL) cooled to 0 C with an ice-bath, was added sodium hydride (60% in mineral oil) in portions. The cooling bath was removed and the mixture was stirred at rt for 15 min. 5-bromopyridine-2-thiol (l.Og, 5.3 mmol) was added in one portion and the reaction mixture stirred at rt for 15 min until the solid dissolved. diethyl 2-chloromalonate was added dropwise, and the reaction mixture was stirred at rt for 2 hr. MeOH was removed under reduced pressure and the reaction mixture was diluted with diethyl ether and quenched by the addition of 1.0 N HC1. The resulting mixture was partitioned between water/diethyl ether. The organic layer was collected, washed with brine and dried over sodium sulfate. The residue was purified by flash chromatography (loading in chloroform, 0% to 30% EtOAc in hexane over 18 min using a 120 g silica gel cartridge). The desired fractions were combined and concentrated under reduced pressure to yield 98a (1.3 g, 71% yield) as a clear oil. LCMS (Method M) retention time = 0.96 min, m/z = 349.8 (M+H)+. NMR (500MHz, chloroFORM-d) 8.47 (dd, J=2.3, 0.7 Hz, IH), 7.66 (dd, J=8.5, 2.5 Hz, IH), 7.17 (dd, J=8.5, 0.8 Hz, IH), 4.29 (q, J=7.2 Hz, 4H), 1.31 (t, J=7.2 Hz, 6H)

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 56673-34-8, 3-Bromo-6-mercaptopyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TORA, George, O.; FINLAY, Heather; JIANG, Wen; MENG, Wei; ZHANG, Xiaojun; (303 pag.)WO2017/218633; (2017); 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. 327056-62-2, name is 2-Cyano-5-fluoropyridine. A new synthetic method of this compound is introduced below., name: 2-Cyano-5-fluoropyridine

The mixture of 5-fluoro-pyridine-2-carbonitrile (0.16 g, 1.27 mmol) and Pd/C (0.030 g, 10% wt) in 15 ml of MeOH and 0.50 ml of concentrated HCl was placed under H2 which was provided by a balloon and stirred at RT for 4 h, filtered through Celite, condensed, the residue was purified by flash column chromatography. The titled compound was obtained as a light yellowish solid. MS (ES+): 127.2 (free base)(M+H)+. Calc’d for C6H7FN2 (free base) 126.13.

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, 327056-62-2, 2-Cyano-5-fluoropyridine.

Reference:
Patent; Amgen Inc.; US2003/225106; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16744-81-3, 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 16744-81-3 as follows.

To the solution of 4-methoxypyridine-2-carbaldehyde (3.00 g, 21 mmol) in 50 ml of dichloromethane was dropwise added ethylenediamine (23 mmol, 1.6 ml) in an ice-water bath. The mixture was stirred for 1 h. Then N-bromosuccinimide (4.1 g, 23 mmol) was added at 0 °C, The mixture was slowly warmed to room temperature and stirred overnight. Washing the reaction mixture with 5percent NaOH solution (50 mL) and then saturated Na2S2O3 solution (50 mL), drying with Na2S04 and removal of the dichloromethane under vacuum directly gave the desired crude product 2-(4,5-dihydro-1H-imidazol-2-yl)-4-methoxypyridine (3.55 g, yield 95percent), which could be used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16744-81-3, its application will become more common.

Reference:
Patent; TIGER INSTRUMENTS, LLC; TANG, Weiping; ZHENG, Junrong; (23 pag.)WO2018/194537; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 688782-02-7, 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 688782-02-7, name is 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 21A N-(2-Fluoro-4-nitrophenyl)-3-methyl-1H-pyrrolo[2,3-b]pyridine-4-amine A solution of 8 mg (50 mumol) of 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, 9 mg (60 mumol) of 2-fluoro-4-nitroaniline, 4 mg (5 mmol) of tris(dibenzylideneacetone)dipalladium and 5 mg (10 mumol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine and 10 mg (70 mumol) of potassium carbonate in 1.00 ml of degassed tert-butanol is stirred at 100 C. in a sealed pressure vessel for 3 h. After cooling to RT, the mixture is filtered through Celite, the Celite is washed with methanol and the filtrates are concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1). Yield: 12 mg (87% of theory) LC-MS (Method 3): Rt=1.63 nm n. MS (ESI pos.): m/z=287 (M+H)+. 1H-NMR (DMSO-d6, 300 MHz): delta=2.13 (s, 3H), 6.82-6.96 (m, 2H), 7.18 (s, 1H), 7.94 (d, 1H), 8.08-8.18 (m, 2H).

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 688782-02-7, 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; Bayer HealthCare AG; US2008/269268; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75806-86-9 ,Some common heterocyclic compound, 75806-86-9, molecular formula is C5H2BrClN2O2, 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 2-bromo-5-chloro-3-nitro-pyridine (CAS RN: 75806-86-9, 360 mg, 1.5 mmol) in DMSO (2 ml) was added thiophene-2-sulfonic acid amide (CAS RN: 6339-87-3, 165 mg, 1.0 mmol) and K2CO3 (276 mg, 2.0 mmol). The mixture was stirred at 60C for 24 h, diluted with EtOAc, extracted with 1 M HCl, brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (0%-100% EtOAc in hexanes) to yield Intermediate 9 (245 mg, 77%) as light brown solid. 1H NMR (METHANOL-d4) delta: 8.57 – 8.63 (m, 2H), 7.95 (dd, J = 4.0, 1.3 Hz, 1 H), 7.86 (dd, J = 5.0, 1.5 Hz, 1H), 7.14 (dd, J = 5.1, 4.0 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75806-86-9, its application will become more common.

Reference:
Patent; ALLERGAN, INC.; Yuan, Haiqing; Beard, Richard, L.; Liu, Xiaoxia; Donello, John E.; Viswanath, Veena; Garst, Michael E.; EP2955173; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem