Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, 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, 10592-27-5, blongs to pyridine-derivatives compound. Application In Synthesis of 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine

A solution OF BR2 (18.1 ML, 56.2 g, 0. 351 mol) in dry CH2CL2 (250 mL) was added dropwise over a period of 1 h 45 min to a stirred and cooled (-5 C) solution of 2 (42. 22 g, 0.351 mol) in dry CH2CL2 (410 ML)-PYRIDINE (40 mL). The yellow suspension WAS STIRRED AT 0 C for 45 min and poured into A mixture of saturated aqueous NaHCO3 (800 ML) and saturated aqueous NA2S203 (100 mL). Methanol (10 ML) was added and the lower organic layer was separated and dried over MGS04. The aqueous layer was extracted with AcOEt: MEOH=99 : 1 (7×1000 mL). These extracts were also dried with MgSO4. The organic solutions were combined and concentrated to afford 5 (59. 17 g, 85%), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) No. 3. 07 (tt, J = 8.4, 1.1 Hz, 2H), 3.64 (T, J = 8. 4 Hz, 2H), 4.47 (bs, 1H), 7.31 (m, 1H), 7. 85 (dt, J= 2.1, 0.9 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,10592-27-5, its application will become more common.

Reference:
Patent; EISAI LONDON RESEARCH LABORATORIES LIMITED; WO2004/78757; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14432-12-3, 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 14432-12-3, name is 4-Amino-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-amino-2-chloropyridine (193 mg, 1.50 mmol), di-tert-butyl-di- carbonate (393 mg, 1.80 mmol) and 4-dimethylaminopyridine (1.8 mg, 0.02 mmol) in acetonitrile (5 mL) was stirred at room temperature for 18 hours. This mixture was concentrated under reduced pressure. The residue was purified by column chroma- tography on silica-gel (hexane/ethyl acetate, 20: 1) to give tert-butyl (2-chloropyridin- 4-YL) carbamate (250 mg, 73%).

According to the analysis of related databases, 14432-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/43926; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 845827-15-8, Adding some certain compound to certain chemical reactions, such as: 845827-15-8, name is Methyl [2,3′-bipyridine]-6′-carboxylate,molecular formula is C12H10N2O2, 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 845827-15-8.

2,3′-Dipyridine-6′-carboxylic acid (1) Conducting the operations similar to those of Production Example 14 using 2-iodopyridine and 6-bromo-3-pyridineboronic acid, 6′-bromo-2,3′-dipyridine was obtained. (2) The compound (330 mg) as obtained in above (1), catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium and triethylamine (0.7 ml) were added to a DMF-methanol mixed solution (DMF/methanol; 5/1 ml) and stirred in carbon monoxide atmosphere at 80C for a day and night, to provide methyl-2,3′- dipyridine-6′-carboxylate (160 mg). Hydrolyzing this with 5N aqueous sodium hydroxide solution, the title compound (110 mg) was obtained as white solid. ESI-MS Found:m/z 201 [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. 845827-15-8, Methyl [2,3′-bipyridine]-6′-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1657242; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 171178-45-3, 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 171178-45-3 as follows.

EXAMPLE 181-(((5S JS)-3-(6-Chloropyridin-3-yl)-7-methyl-2-oxo-1-oxa-3-azaspiror4.5ldecan-7-yl)methyl)-1 H-benzordlimidazole-6-carbonitrileA 5 ml. microwave vial was charged with 1-(((3S,5S)-5-methyl-1-oxaspiro[2.5]octan-5- yl)methyl)-1 H-benzo[d]imidazole-6-carbonitrile (200 mg, 0.711 mmol), tert-butyl (6-chloropyridin- 3-yl)carbamate (195 mg, 0.853 mmol), potassium tert-butoxide (96 mg, 0.853 mmol) and DMF. The tube was sealed and heated to 70 C for 16 h. The reaction mixture was loaded onto a 10 g SCX SPE and eluted with 3 volumes of MeOH followed by 3 volumes of 2N ammonia in MeOH. The ammonia fractions were combined and concentrated and the crude product then purified by Waters reverse phase HPLC (20% to 60% MeCN, 0.1 %TFA, 16 min, 50 mL/min, Sunfire column) to afford the TFA salt of 1-(((5S,7S)-3-(6-chloropyridin-3-yl)-7-methyl-2-oxo-1- oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1 H-benzo[d]imidazole-6-carbonitrile as a cream solid (55 mg, 12.67 % yield). MS (m/z) 435.9 (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,171178-45-3, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, 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: 175205-82-0, blongs to pyridine-derivatives compound. SDS of cas: 175205-82-0

Step 2. Synthesis of methyl 3-amino-6-(3-(trifluoromethyl)pyridin-2-yl)pyrazine-2- carboxylate In a 500 mL round-bottom flask equipped with a magnetic stirrer and argon inlet, methyl 3-amino-6-(trimethylstannyl)pyrazine-2-carboxylate (20.92 g, 55.0 mmol), 2-Bromo-3- (trifluoromethyl) pyridine (14.38 g, 60.5 mmol), Pd2(dba)3 (5.54 g, 6.05 mmol) and P(o-Tol)3 (3.79 g, 12.09 mmol) were dissolved in DMF (100 ml) at rt, followed by addition of NEt3 (10.72 ml, 77 mmol). The reaction mixture was heated to 110C under argon for 1 h. After cooling to rt, the reaction mixture was filtered through celite, washed with ethyl acetate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using ethyl acetate heptane which gave methyl 3-amino-6-(3-(trifluoromethyl)pyridin-2-yl)pyrazine-2- carboxylate (7.8 g) as a yellow solid. LC-MS (Basic Method ): ret.time= 0.93 min, M+H = 299.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LUZZIO, Michael Joseph; PAPILLON, Julien; VISSER, Michael Scott; (213 pag.)WO2016/20864; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83004-10-8, 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 83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: General procedure B: To a 5 mL vial back-filled with dried air,compound 1 (1.0 equiv., 0.2 mmol), benzyl bromides (6.0 equiv., 1.2 mmol), and Na2CO3 (2.0 equiv. 0.4 mmol, 42 mg) in sulfolane (0.5 mL) were added, and the reaction was heated at 90 C for 18 h. Upon the completion of the starting materials, the reaction mixture was dissolved in 100 mL H2O, and extracted with dichloromethane (40 mL 3). The organic layers were combined, dried over anhydrous Na2SO4, and removed. The crude was purified by using silica gel column chromatography (PE/EA 10:1e1:2 as eluents) to afford the target compound 2.

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 83004-10-8, 2-Bromo-6-(bromomethyl)pyridine.

Reference:
Article; Xu, Huayan; Xu, Liang; Luo, Xiaowei; Wang, Junfeng; Zhou, Xuefeng; Yang, Bin; Li, Ding; Luo, Zaigang; Liu, Yonghong; Liao, Shengrong; Tetrahedron; vol. 75; 19; (2019); p. 2785 – 2796;,
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. 76006-13-8, name is 3-Bromo-1H-pyrazolo[3,4-c]pyridine, the common compound, a new synthetic route is introduced below. Safety of 3-Bromo-1H-pyrazolo[3,4-c]pyridine

ii) Preparation of 3-bromo-1-(2-chloro-6-(trifluoromethyl)benzyl)-1H-pyrazolo[4,3-b]pyridine (A-4) A mixture of 2-chloro-6-(trifluoromethyl)benzyl 4-methylbenzenesulfonate (A-2) (0.19 g, 0.51 mmol), 3-bromo-1H-pyrazolo[3,4-c]pyridine (A-3) (0.1 g, 0.51 mmol), t-BuOK (0.11 g, 1.02 mmol) and TBAI (75 mg, 0.20 mmol) in THF (5 ml) was heated at 60 C. for 14 h. The reaction mixture was cooled down, diluted with saturated NH4Cl solution (20 ml) and extracted with ethyl acetate (30 ml*2). The combined organic layers were washed with brine (20 ml), dried over anhydrous Na2SO4 and concentrated to give the title compound A-4 as a brown oil. LCMS (ESI) calc’d for C14H8BrClF3N3 [M+H]+: 390. found: 390.

The synthetic route of 76006-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barr, Kenneth J.; Bienstock, Corey E.; MacLean, John K.; Zhang, Hongjun; Beresis, Richard T.; Anthony, Neville J.; Lapointe, Blair T.; Sciammetta, Nunzio; US2015/210687; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, 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. Product Details of 15862-37-0

A 150 mL pressure flask was charged with (6-chloro-2-methoxypyridin-3- yl)boronic acid (2.5 g, 13.3 mmol) and 2,5-dibromo-3-nitropyridine (3.38 g, 12.01 mmol). The solids were suspended in THF (60 mL). The mixture was treated with PdCl2(dppf)-CH2Cl2 adduct (0.545 g, 0.667 mmol) and K3P04 (2M, 20 mL, 40 mmol). Argon was bubbled through the mixture for 5 min while sonicating. The flask was capped and heated to 80C in a preheated oil bath. The reaction was cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated to remove THF. The remaining water layer was diluted further with water and was extracted with ethyl acetate. The organic layer was dried over MgS04, filtered and concentrated under vacuum to give a solid. The material was taken up in DCM and a minimum of ethyl acetate and purified by flash column chromatography (80g ISCO column, 0-30% ethyl acetate/hexanes over 600 mL, then 50-100% over 300 mL). Like fractions were concentrated to give 4.5g (78%). NMR (400MHz, CDCh) delta 8.94 (d, J=2.0 Hz, 1H), 8.44 (d, J=2.0 Hz, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.14 (d, J=7.8 Hz, 1H), 3.89 (s, 3H). LC/MS (M+H) = 345.95

With the rapid development of chemical substances, we look forward to future research findings about 15862-37-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); 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 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Safety of tert-Butyl (6-chloropyridin-3-yl)carbamate

1,1-Dimethylethyl (6-Chloro-4-iodo-3-pyridinyl)carbamate n-Butyllithium (1.6M in hexanes, 22 mL, 35 mmol) was added dropwise to a stirred, cooled (-78 C.) solution of 1,1-dimethylethyl (6-chloro-3-pyridinyl)carbamate (Description 6, 2.68 g, 11.7 mmol) and N,N,N’,N’-tetramethylethylenediamine (5.3 mL, 4.1 g, 35 mmol) in ether (60 mL). The mixture was allowed to warm to -10 C. and stirred for 2 h. The mixture was cooled to -78 C. and a cooled (-10 C.) solution of iodine (6.0 g, 24 mmol) in ether (20 mL) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 18 h. Saturated aqueous ammonium chloride was added and the mixture was extracted with ether. The combined organic fractions were washed with aqueous sodium metabisulfite (10%), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with hexane and the solid was collected and dried in vacuo to give the title compound as a brown solid (2.3 g, 55%). 1H NMR (400 MHz, CDCl3) delta 8.94 (1H, s), 7.73 (1H, s), 6.64 (1H, br s), and 1.54 (9H, s).

With the rapid development of chemical substances, we look forward to future research findings about 171178-45-3.

Reference:
Patent; Dinnell, Kevin; Elliott, Jason Matthew; Hollingworth, Gregory John; Shaw, Duncan Edward; US2002/22624; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 21427-62-3 ,Some common heterocyclic compound, 21427-62-3, molecular formula is C5H2Cl2N2O2, 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.

Example 10; (+/-)-9-[Acetyl-(3,5-bis-trifluoromethylbenzyl)amino]-3-chloro-2-methoxy-6,7,8,9- tetrahydro-pyrido[3,2-b]azepine-5-carboxylic acid isopropyl ester; Step 1;. Preparation of 5-Chloro-3-nitro-pyridine-2-carbonitrile; Add 3-nitro-5-chloro-pyridin-2-ol (3.9 g, 22.3 mmol) to a mixture of phosphorous oxychloride (4.17 mL) and dimethylformamide (10 mL). Heat the resulting mixture at 110 C for 30 min. Cool the reaction mixture to room temperature and pour onto ice- water. Add sodium bicarbonate slowly until neutralization occurs and extract with ethyl acetate. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Dissolve the residue in N-methyl pyrrolidinone (4 mL), add copper (I) cyanide (2.39 g, 26.7 mmol) and heat at 160 C for 15 min. Cool the reaction mixture to room temperature and pour onto ice water and ethyl acet ate. Add a saturated solution of sodium bicarbonate, separate the organic layer, and extract the aqueous layer with ethyl acetate. Dry the combined organic layers over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue using silica gel chromatography, eluting with ethyl acetate/hexanes 1: 3 to afford the title cornpound (1.01 g, 26%). H-NMR (CDC13, 300 MHz) : No. 8.61 (s, 1H), 8.95 (s, 1H).

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. 21427-62-3, 2,5-Dichloro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/97805; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem