Tag: M.W:100-200

Application of 131747-63-2 ,Some common heterocyclic compound, 131747-63-2, molecular formula is C6H4BrNO, 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.

A solution of 4-bromopyridine-2-carboxaldehyde (10 g), trimethyl orthoformate (23.3 mL) and PTSA (1.51 g) in Me OH (261 mL) was stirred at reflux for 1 day. Sat. aq. NaHC03 and EA were added, the layers were separated and the aq. layer was twice extracted with EA, dried over MgSOzt, filtered and concentrated under reduced pressure. The crude product was purified by filtration over 200 mL silicagel using Hept/EA 1/1 as solvent. The title compound was obtained as a colourless liquid (11.5 g; 95% yield). MS I (ESI, m/z): 231.99 [M+H+]; tR = 0.63 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131747-63-2, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CREN, Sylvaine; RUEEDI, Georg; ZUMBRUNN, Cornelia; (60 pag.)WO2017/179002; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60290-21-3, 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. 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5ClN2, 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.

Intermediate 13-Bromo-4-chloro-lH-pyrrolo[3No.2-c]pyridine; [00124] To a solution of the amine (2.18 g, 14.2 mmol) in THF (60 mL) was added Mntheta2 (7 g, 80.5 mmol) and the mixture was heated to reflux. After 5 h, a further portion of MnO2 (3 g, 34.5 mmol) was added and stirring continued overnight. The reaction was filtered through Celite and concentrated to give a white solid (1.95 g, 91%) .[00125] The indole (1.48 g, 9.72 mmol) was dissolved in CH2C12 (50 mL) and cooled to 0 aC under nitrogen. N- Bromosuccinimide (1.82 g, 10.2 mmol) was added and after 30 min the ice-bath was removed and stirring continued for a further 30 min. The desired bromide (1.53 g, 68%) was filtered off and dried on high vacuum. MS (ES+) m/e = 231. IH NMR (DMSO) 7.48 (IH, d) , 7.80 (IH, s), 8.00 (lH, d) .

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 60290-21-3, 4-Chloro-1H-pyrrolo[3,2-c]pyridine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/95223; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56809-84-8, 3,4-Dichloro-5-nitropyridine, 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, 56809-84-8, blongs to pyridine-derivatives compound. Formula: C5H2Cl2N2O2

To a solution of intermediate 18-b (25 g 125.94 mmol) in ethanol (250 mL) was added cyclopropylamine (11.10 g, 194.31 mmol). The solution was warmed to 80C for 1 hour. The solvent was evaporated and water was added. The resulting mixture was extracted with dichloromethane (3×50 mL). The organic layer was washed with brine, dried with MgSC^ and concentrated. The intermediate 18-c was obtained (26 g, 94%>).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56809-84-8, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; TAHRI, Abdellah; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; VENDEVILLE, Sandrine Marie Helene; HU, Lili; WO2013/186335; (2013); 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. 7579-20-6, name is 3-Aminoisonicotinic acid. A new synthetic method of this compound is introduced below., name: 3-Aminoisonicotinic acid

3- Aminoisonicotinic acid (1 g, 7.24 mmol) was carefully added in 3 aliquots to a slurry of UAIH4 (0.99 g, 26.1 mmol) in dry tetrahydrofuran (40 ml). The resulting mixture was stirred at 15°C overnight. After cooling in an ice bath, the reaction mixture was quenched with careful addition of water (1 ml) dropwise, followed by 15percent aqueous NaOH (1 ml), and then water (3 ml). The resulting solid was filtered, and washed several times with tetrahydrofuran. The filtrate was concentrated to give oil, which was purified by flash chromatography on silica gel using 5percent CH3OH Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
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

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

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-04-6, 2-Bromopyridine, 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, Product Details of 109-04-6, blongs to pyridine-derivatives compound. Product Details of 109-04-6

Example 1: Preparation of 2-(4-chloro-phenyl)pyridine; [53] Under a nitrogen stream, 5.0 g (0.032 mol) of 4-chloro-phenyl boronic acid, 10.0 g(0.064 mol) of 2-bromopyridine, 150 D of tetrahydrofuran and 2M potassium carbonate solution (20 D) were placed into a 2-neck round flask 250 D and then 0.37 g (3 mol%) of palladium tetrakistriphenylphosphine [(pd(PPh ) ] was added as a catalyst. After the resulting solution was heated to reflux at 8O0C for 24 hours, the reaction was terminated. The resulting mixture was poured into a beaker containing 200 D of distilled water. After extraction with ether (150 D) three times, 10 g of magnesium sulfate was added. The resulting solution was stirred by a rotary stirrer for 30 minutes and then the extraction mixture was filtered. After removing the solvent using a rotary evaporator, the residue was subjected to column chromatography using dichloromethane as a developing solvent and then distilled under reduced pressure to give the 2-(4-chloro-phenyl)pyridine. The yield was 56%.[54] The H-NHR spectrum is shown in Fig. 1 to confirm the structure of the thus prepared 2-(4-chloro-phenyl)pyridine.

The synthetic route of 109-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GWANGJU INSTITUTE OF SCIENCE AND TECHNOLOGY; WO2007/129810; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem