Pyridine-derivatives

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. 102625-64-9, name is 5-(Difluoromethoxy)-2-(((3,4-dimethoxypyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole, molecular formula is C16H15F2N3O3S, 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. Recommanded Product: 102625-64-9

At room temperature, 20.2 g of 5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridinyl)methylthio]-1H-benzimidazole are suspended in 100 ml of methyl isobutyl ketone together with 18.0 g of (+)-L-tartaric acid bis-(N,N-dimethylamide) and 13.4 g of zirconium(IV) isopropoxide/isopropanol. The mixture is heated at 40C for one hour, resulting in the formation of a solution which is almost clear. After cooling to room temperature, 4.1 ml of N-ethyldiisopropylamine are added. 11 ml of cumene hydroperoxide are then slowly metered in. Stirring is continued at room temperature until the oxidation has ended (5-10 hours, monitored by TLC). The clear solution is diluted with 100 ml of methyl isobutyl ketone and quenched with 1.8 g of sodium thiosulphate in 140 ml of water and stirred for a further 14 hours. After phase separation, 55 ml of saturated sodium bicarbonate solution and 55 ml of methyl isobutyl ketone are added to the aqueous phase, and the phases are separated. Another 55 ml of saturated sodium bicarbonate solution and 55 ml of methyl isobutyl ketone are added to the aqueous phase, and the phases are separated. The combined methyl isobutyl ketone phases are then washed twice with 55 ml of saturated sodium bicarbonate solution. 150 mi of water are added to the methyl isobutyl ketone phase, and the pH is adjusted to pH = 13 using a 40% by weight strength aqueous solution of sodium hydroxide. After phase separation, the methyl isobutyl ketone phase is extracted with another 50 ml of water at pH = 13. The aqueous phases are combined and, at 40C, subjected to incipient distillation under reduced pressure. At 40-45C, (-)-pantoprazole is precipitated by addition of 10% strength acetic acid to pH = 9.0. Stirring is continued for another 12 hours during which the pH is monitored. The beige crystals are filtered off and washed with 50 ml of water. The title compound is obtained in a yield of about 15 g (73% of theory) and an optical purity of >95%. To increase the purity, (-)-pantoprazole is dissolved in water/aqueous sodium hydroxide solution at pH = 13 and re-precipitated with acetic acid (10%) at pH = 9.0.

With the rapid development of chemical substances, we look forward to future research findings about 102625-64-9.

Reference:
Patent; ALTANA PHARMA AG; WO2004/52882; (2004); A1;,
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Synthetic Route of 944401-77-8, 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. 944401-77-8, name is 2-Amino-4-fluoropyridine, molecular formula is C5H5FN2, 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.

25 g 2-amino-4-fluoropyridine was added to200ml of ethylene glycol dimethyl ether, was added 54g ethyl 3-bromopyruvate, stirred overnight at room temperature, concentrated and then added ethyl acetate and water, liquid separation, dried, concentrated and the residue on the column to give 28g7-Fluoro-imidazo [1,2-a] pyridine-2-carboxylic acid ethyl ester.

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 944401-77-8, 2-Amino-4-fluoropyridine.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (5 pag.)CN107286154; (2017); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 779345-37-8, name is 5-Fluoro-2-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 779345-37-8

To a solution of 2-bromo-4,6-dichlorophenol (2, 2.0 g, 14.0 mmol) in MeCN (20 ml), Cs2CO3 (5.50 g, 17.0 mmol) was added. After stirring at room temperature for 15 min, 5-fluoro-2-nitropyridine (12, 2.45 g, 14.0 mmol) was added dropwise and the reaction mixture was sealed for 16 h at 80 C. The reaction was concentrated in vacuo. The residue was purified by flash column chromatography [normal phase, silica gel (100-200 mesh), gradient 10% to 15% ethyl acetate in hexane] and then triturated with pentane (100 ml) to give 5-(2-bromo-4,6-dichlorophenoxy)-2-nitropyridine (13, 1.5 g, 50%) as an off-white solid. MS (ESI -ve): 363 1H-NMR (400 MHz; CDCl3): d 7.28 (d, J = 2.3 Hz, 1H), 7.52 (s, 1H), 7.64 (s, 1H), 8.22 – 8.30 (m, 2H).

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, 779345-37-8, 5-Fluoro-2-nitropyridine.

Reference:
Article; O’Brien, Alistair; Andrews, Stephen P.; Baig, Asma H.; Bortolato, Andrea; Brown, Alastair J.H.; Brown, Giles A.; Brown, Sue H.; Christopher, John A.; Congreve, Miles; Cooke, Robert M.; De Graaf, Chris; Errey, James C.; Fieldhouse, Charlotte; Jazayeri, Ali; Marshall, Fiona H.; Mason, Jonathan S.; Mobarec, Juan Carlos; Okrasa, Krzysztof; Steele, Kelly N.; Southall, Stacey M.; Teobald, Iryna; Watson, Steve P.; Weir, Malcolm; Bioorganic and Medicinal Chemistry Letters; vol. 29; 20; (2019);,
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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 70201-42-2, name is 3,5-Dibromoisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. name: 3,5-Dibromoisonicotinaldehyde

Example 126a 3-Bromo-5-(1-oxo-6,7,8,9-tetrahydropyrazino[1,2-a]indol-2(1H)-yl)isonicotinaldehyde 126a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (15 mL), 3,5-dibromoisonicotinaldehyde (604 mg, 2.28 mmol), 6,7,8,9-tetrahydropyrazino[1,2-a]indol-1(2H)-one (142 mg, 0.76 mmol) and cesium carbonate (485 mg, 1.5 mmol). CuI (143 mg, 0.76 mmol) and 4,7-dimethoxy-1,10-phenanthroline (127 mg, 0.52 mmol) were added, and the reaction mixture was heated at 100 C for 5 h. After this time, the reaction was cooled to room temperature. It was then filtered and the filtrate was concentrated under reduced pressure. The residue was purified on flash column eluting with EtOAC/PE (1:2) to afford 126a (100 mg, 35%) as a yellow solid. MS: [M+H]+ 372.

With the rapid development of chemical substances, we look forward to future research findings about 70201-42-2.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 85333-26-2, Adding some certain compound to certain chemical reactions, such as: 85333-26-2, name is 2-Amino-4-benzyloxypyridine,molecular formula is C12H12N2O, 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 85333-26-2.

A mixture of 2-amino-4-benzyloxypyridine (2.00 g, 9.49 mmol), copper (I) bromide (70 mg, 0.05 mmol), 1,10-phenanthroline monohydrate (95 mg, 0.05 mmol) and benzonitrile (25 mL) was heated in a 50-mL 3-necked flask to 130 C. During 23 h a gentle flow of (O2/N2 5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below). The dark brown solution was then evaporated at 60 C./0.1 mbar to dryness and the dark brown residue dissolved in DCM (30 mL). The organic solution was washed with water (30 mL), dried over sodium sulphate, filtered and evaporated to yield an dark oil containing crude 7-benzyloxy-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine and residual benzonitrile. [0099] Charcoal treatment of the crude product with Norit SA II (0.90 g) in EtOAc (120 mL) at reflux, filtration and subsequent crystallization (via partial evaporation of EtOAc and addition of heptane) afforded 7-benzyloxy-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (1.78 g, 62%) as an off-white solid with >99.9% purity (HPLC area-%, HPLC method: Onyx monolithic C18 column, 100×4.6 mm; mobile phase, A: water/NCMe (95:5), B: NCMe; flow: 2.0 ml/min; gradient from 95/5 (A/B) to 15/85 (A/B) within 3 min, isocratic 15/85 (A/B) for 2.5 min. Retention time: 3.40 min (2-amino-4-benzyloxypyridine), 3.60 min 7-benzyloxy-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine)). [0100] EI-MS: m/z=302.13 (M+H)+.

According to the analysis of related databases, 85333-26-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HOFFMANN-LA ROCHE INC.; Bartels, Bjoern; Fantasia, Serena Maria; Flohr, Alexander; Puentener, Kurt; Wang, Shaoning; US2014/350259; (2014); 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. 180340-69-6, name is 6-Amino-5-bromonicotinic acid, molecular formula is C6H5BrN2O2, 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. SDS of cas: 180340-69-6

REFERENCE EXAMPLE 191 Methyl 6-amino-5-bromopyridine-3-carboxylate 6-Amino-5-bromopyridine-3-carboxylic acid (10 g, 50 mmol) is dissolved in saturated methanolic HCl (100 ml) and refluxed for 24 hours. The solvent, methanol, is re-moved under reduced pressure and the residue is dissolved in ice cold water. The aqueous solution is neutralized with 0.1N NaOH and the solid which separates is filtered; washed well with water and air dried to yield 10 g of product as a solid: mass spectrum 231 (M+).

With the rapid development of chemical substances, we look forward to future research findings about 180340-69-6.

Reference:
Patent; American Cyanamid Company; US5532235; (1996); A;; ; Patent; American Cyanamid Company; US5654297; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 769-27-7 , The common heterocyclic compound, 769-27-7, name is 6-Amino-2,4-dimethylnicotinonitrile, molecular formula is C8H9N3, 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 15 ( )-6-((4-Amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyl)quinazolin-2-yl)amino)-2,4- dimethylnicotinonitrile- Compound 15 Synthesis of (£)-6-((4-amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyl)quinazolin-2- yl)amino)-2,4-dimethylnicotinonitrile (compound 15) Compound 15 [0279] Compound 2a (20 mg, 0.06 mmol), 6-amino-2,4-dimethylnicotinonitrile (26 mg, 0.18 mmol, Key Organics Ltd, 1X-0933), N,N-diisopropylethylamine (622 mg, 0.48 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4 mg, 0.006 mmol) and palladium (II) acetate (1 mg, 0.006 mmol) were combined under argon in N-methyl-2- pyrrolidone (1 mL). The reaction was heated at 120C in a sealed vessel for 4 hours. The reaction mixture was cooled down to room temperature and diluted with water and ethyl acetate. The organic layer was separated and washed twice with brine, dried over magnesium sulfate and this solution was filtered through a 2 cm layer of silica gel which was washed with additional ethyl acetate. Combined organics were concentrated down under reduced pressure. The crude residue was treated with diethyl ether in the sonic bath for 5 minutes. The solid compound was filtered off and washed twice with diethyl ether and once with hexane to afford the title compound 15. NMR (400 MHz, DMSO-i/6) delta 9.56 (bs, 1 H), 9.29 (bs, 1 H), 8.44 (d, J = 8.0 Hz, 1 H), 7.99 – 7.47 (m, 5H), 7.41 -7.10 (m, 1 H), 6.55 (d, J = 16.7 Hz, 1 H), 2.41 (bs, 3H), 1.96 (s, 6H), 1.62 (bs, 3H). LCMS (m/z) 446.4 [M+H], Tr = 1.19 min (LCMS method 3).

The synthetic route of 769-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; SIMON, Tetr; LANSDON, Eric; HU, Yunfeng, Eric; BASZCZYNSKI, Ondrejj; DEJMEK, Milan; MACKMAN, Richard, L.; (185 pag.)WO2016/105564; (2016); A1;,
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Pyridine | C5H5N – PubChem

Application of 15128-82-2, 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 15128-82-2, name is 2-Nitropyridin-3-ol. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-hydroxy-2-nitropyridine (176.0 g, 1.256 mol) in aqueous sodiumhydroxide (74.0 mL of 50% NaOH in 1.94 L water, 1.40 mol) was cooled at 3.3 C whiledibromantin (198.5 g, 0.694 mol) was added portion-wise over 58 minutes maintaining reaction temperature at or below 4 C. The reaction mixture was then allowed to warm to room temperature overnight. The reaction was quenched with acetic acid (80.0 mL, 1.34 mol), and the resulting slurry was stirred at room temperature for 4 h. The solids werecollected by filtration, washed with water (3 x 300 mL), and then vacuum-dried (35C) overnight to give 148.3 g (54%) of 2-bromo-5-hydroxy-6-nitropyridine as a yellow solid with a purity of 97.8% (LC).

According to the analysis of related databases, 15128-82-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NAVIDEA BIOPHARMACEUTICALS, INC.; CESATI, Richard R., III; CASEBIER, David S.; MORETON, Richard Christian; (49 pag.)WO2017/87965; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 183208-22-2, 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.183208-22-2, name is 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, molecular weight is 211.06, as common compound, the synthetic route is as follows.

To a solution of 5-bromo-1-methyl-1H-pyrrolo[2,3-bjpyridine (800 mg, 3.8 mmol) in MeOH (15 mL) were added Pd(dppf)C12 (272 mg, 0.38 mmol) and TEA (1.15 g, 11.4 mmol). The mixture was stirred at 80 C under CO (1 atm) overnight. The solvent was removed and the residue was purified by silica gel column (100-200 mush, PE/EA = 10/1) to give 1-methyl-1H-pyrrolo[2,3-bjpyridine-5-carboxylic acid methyl ester (665 mg, yield: 91%) as a yellow solid.?HNMR (300 MI-Tz, CDC13): = 9.00 (s, 1H), 8.57 (d, J= 1.2 Hz, 1H), 7.25 (d, J= 3.6 Hz, 1H), 6.55 (d, J 3.3 Hz, 1H), 3.96 (s, 3H), 3.92 (s, 3H). MS: m/z 191.0 (M+H).

The chemical industry reduces the impact on the environment during synthesis 183208-22-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74976-31-1 , The common heterocyclic compound, 74976-31-1, name is 6-Chloro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5ClN2, 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 6-chloro-1H-pyrrolo[3,2-c]pyridine (153 mg, 1.00 mmol) in DMF (5 mL) were added PhSO2Cl (195 mg, 1.10 mmol) and Cs2CO3 (653 mg, 2.01 mmol), and the resulting mixture was stirred at 60 C. for 3 h then concentrated under reduced pressure. The residue was treated with H2O (20 mL), and the mixture was extracted with EtOAc (3*10 mL). The combined organic layers were washed with sat. aq. NaCl, dried over MgSO4, filtered and concentrated under reduced pressure to give the crude title compound as a yellow solid (290 g, 99%), which was used without further purification. MS (ES+) C13H9ClN2O2S requires: 292, found: 293 [M+H]+.

The synthetic route of 74976-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; LE, Kang; SOTH, Michael J.; JONES, Philip; CROSS, Jason Bryant; CARROLL, Christopher L.; MCAFOOS, Timothy Joseph; MANDAL, Pijus Kumar; US2019/298729; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem