Category: pyridine-derivatives

Related Products of 884494-37-5, 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. 884494-37-5, name is 2-Bromo-3-fluoro-4-picoline. A new synthetic method of this compound is introduced below.

To a sealed tube was added 2-bromo-3-fluoro-4-methylpyridine (25.7 mg, 0.135 mmol), 4-methoxy-6-(tributylstannyl)pyrimidine (45 mg, 0.113 mmol), toluene (1.5 mL) and Pd(PPh3)4 (13.03 mg, 0.0 11 mmol). The reaction was purged with Ar and thensealed and stirred at 120 C overnight. The reaction was partitioned between EtOAc (25 ml) and water (20 ml). The organic layer was separated, washed with sat NaC1 (10 ml), dried over MgSO4, filtered and concentrated. The crude product was purified using prepHPLC to give 4-(3 -fluoro-4-methylpyridin-2-yl)-6-methoxypyrimidine trifluoroacetate (20 mg, 0.060 mmol, 53.2% yield) as a purple salt. ?H NMR (400MHz, CDC13) oe 9.22 (s,1H), 8.59 (d, J=4.2 Hz, 1H), 7.56 (s, 1H), 7.51 (br. s., 1H), 4.23 (s, 3H), 2.51 (s, 3H); MS(ESI) m/z: 220.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-37-5, 2-Bromo-3-fluoro-4-picoline, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 504-29-0, Adding some certain compound to certain chemical reactions, such as: 504-29-0, name is Pyridin-2-amine,molecular formula is C5H6N2, 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 504-29-0.

2-Aminopyridine (4.7 g,50 mmol) was dissolved in a mixture of water (6 mL),glacial acetic acid (120 mL), and concentrated sulfuricacid (1 mL) preliminarily cooled to room temperature. Upon mixing, iodine (6 g, 23.6 mmol) and NaIO4(1.6 g, 7.5 mmol) were added. The mixture was kept at80C for 4 h, then 200 mL of 10% sodium thiosulfate solution was added and extracted with ethyl acetate(3 ¡Á 150 mL). The organic phase was washed with10% sodium hydroxide solution (3 ¡Á 60 mL) and brine(2 ¡Á 50 mL), dried over anhydrous Na2SO4, evaporated,and purified by flash chromatography (chloroform-ethanol, 50 : 1). Violet powder (10.3 g, 94%);1H NMR: 8.04 (d, J2 2.1, 1H), 7.58 (dd, J2 8.6, 2.2,1H), 6.35 (d, J2 8.6, 1H), 6.10 (br, 2H).

According to the analysis of related databases, 504-29-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Baleeva, N. S.; Baranov, M. S.; Smirnov, A. Yu.; Zaitseva, E. R.; Zaitseva, S. O.; Russian Journal of Bioorganic Chemistry; vol. 46; 1; (2020); p. 120 – 123; Bioorg. Khim.; vol. 46; 1; (2020); p. 120 – 123,4;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74764-17-3, N1-(Pyridin-2-yl)ethane-1,2-diamine, 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, Quality Control of N1-(Pyridin-2-yl)ethane-1,2-diamine, blongs to pyridine-derivatives compound. Quality Control of N1-(Pyridin-2-yl)ethane-1,2-diamine

Step 7 5-Amino-6-fluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-7-[2-(2-pyridylamino)ethylamino]-3-quinolinecarboxylic Acid A mixture of 5-amino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylic acid (45.0 mg, 0.139 mmol), 2-(2-pyridylamino)ethylamine (29.0 mg, 0.211 mmol), and triethylamine (0.029 mL, 0.209 mmol) in DMSO (1.0 mL) was stirred at 120 C. for 3 h. After dilution of the reaction mixture with 10% MeOH in CHCl3, the whole mixture washed with water, and the washing was extracted with 10% MeOH in CHCl3 two times. The combined the organic layer and the extracts washed with water, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash chromatography of the residue (10% MeOH in CHCl3) gave 5-Amino-6-fluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-7-[2-(2-pyridylamino)ethylamino]-3-quinolinecarboxylic Acid (54.0 mg, 88%) as a white powder. 1H NMR (400 MHz, DMSO-d6) delta 1.88-2.02 (4H, m), 3.40-3.60 (6H, m), 3.94-3.98 (2H, m), 4.71-4.78 (1H, m), 6.18 (1H, d, J=6.7 Hz), 6.46-6.51 (2H, m), 6.75 (1H, t, J=6.1 Hz), 6.94 (1H, br), 7.20 (1H, br), 7.34-7.38 (1H, m), 7.98-7.99 (1H, m), 8.47 (1H, s), 15.5 (1H, s). MS (ESI+) m/z 442 (M++H).

The synthetic route of 74764-17-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cociorva, Oana; Li, Bei; Szardenings, Katrin; Fukuda, Yasumichi; Nomura, Masahiro; Seto, Shigeki; Yumoto, Kazuhiro; Okada, Kyoko; Nakamura, Ayako; US2007/254866; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16133-25-8, 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. 16133-25-8, name is Pyridine-3-sulfonyl chloride. A new synthetic method of this compound is introduced below.

In 500m reaction flask, 200ml of acetonitrile was added,5- (2-fluorophenyl) -1H-pyrrole-3-carbonitrile (50 g, 0.27 mol),N, N-diisopropylethylamine (41.6 g 0.32 mol) and4-N, N-dimethylaminopyridine (4.69 g, 38.4 mmol),Stir at room temperature. The temperature of the reaction solution was controlled to be not higher than 30 ¡ã C, and a mixed solution of 3-pyridinesulfonyl chloride (52.5 g, 0.29 mol) in 100 ml of acetonitrile was added dropwise.Dropping completed, 25 ¡ã C for 2 hours, the reaction is completed, 300ml of purified water was added to the reaction solution, the reaction temperature was controlled not higher than 30 ¡ã C, the dropwise addition of concentrated hydrochloric acid to adjust the pH to 4-5, 25 ¡ã C with stirring 2 hours, filtered, washed with a mixture of acetonitrile and water, and the solid was collected and dried under reduced pressure at 50 ¡ã C to give 79.5 g of 5- (2-fluorophenyl) -1- (pyridin-3-ylsulfonyl) 3-Nitrile yield 90 ? 5percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16133-25-8, its application will become more common.

Reference:
Patent; Shandong Kangmeile Pharmaceutical Technology Co., Ltd.; Geng Fengluan; Liu Yunfeng; Liu Xiaojun; (8 pag.)CN104860923; (2018); B;,
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. 13534-97-9, name is 6-Bromopyridin-3-amine, molecular formula is C5H5BrN2, 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. HPLC of Formula: C5H5BrN2

2. Preparation of diethyl 2-((6-bromopyridine-3-ylamino)methylene)malonate 6-bromopyridine-3-amine (74g, 0.43mol) and diethyl ethoxymethylenemalonate (100mL) were added ethanol (680mL). The mixture is reacted under heating to reflux for 5h. The reaction mixture was cooled. The solid was separated out and filtered by suction. The resulting solid was washed with petroleum ether to produce 125.4g of the title compound as a pale-yellow solid in a yield of 85.2%.

With the rapid development of chemical substances, we look forward to future research findings about 13534-97-9.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; ZHANG, Yan; EP2719697; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 571189-49-6, 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 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-chloro-6-(2-(4-fluorophenyl)pyrrolidin-1-yl)pyrimidine compound 6 (200 mg, 0.720 mmol), 5-(4-methylpiperazin-1-yl)pyridin-2-amine compound 15 (152.30 mg, 0.792 mmol), xantphos (4,5-diphenylphosphanyl-9,9?-dimethyl-9-H-xanthene, 104.17 mg, 0.180 mmol), K2CO3 (497.63 mg, 3.60 mmol) and palladium(II) acetate (24.25 mg, 0.108 mmol) in 1,4-dioxane (10 ml) was purged with argon for 1 hour. The mixture was heated in an oil bath for overnight at 105 C. TLC was checked and the starting material was consumed. After cooling to room temperature, the reaction mixture was passed through a pad of celite using 10% MeOH/DCM and was concentrated. The crude product was purified by column chromatography (silica gel, 0-10% MeOH in DCM) to obtain compound 61 as brown solids (244 mg, 78% yield). 1H NMR (400 MHz, DMSO-d6) deltadelta 9.28 (s, 1H), 8.07 (s, 1H), 7.82 (s, 1H), 7.34 (m, 2H), 7.23 (m, 2H), 7.14 (m, 2H), 6.72 (br, 1H), 5.02 (br, 1H), 3.74 (m, 2H), 3.17 (m, 4H), 2.47-2.44 (m, 4H), 2.38 (s, 3H), 2.00-1.75 (m, 4H); ESI-MS: calcd for (C24H28FN7) 433, found 434 (MH+).

According to the analysis of related databases, 571189-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NantBio, Inc.; Tao, Chunlin; Wang, Qinwei; Asad, Sharif; Weingarten, Paul; Ci, Sherry; US2018/346451; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 126053-15-4, 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 126053-15-4 as follows.

A mixture of intermediate 4 (0.0002 mol) and 4-chloro-6,7-dihydro-5/-/- cyclopenta[b]pyridin-7-ol (0.0002 mol) in HCI/dioxane 4N (14mul), CH3CN (1 ml) and EtOH (0.5ml) was stirred at 65C for 18 hours. HCI (0.2eq) and dioxane 4N (14mul) were added. The mixture was stirred at 65C for 18 hours, then cooled to room temperature, diluted in CH2CI2 and washed with K2CO3 10% aqueous solution. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (0.14g) was purified by column chromatography over Sunfire (eluent: CH2CI2/CH3OH/NH4OH 100/0/0 to 92/8/0.8; 5mum). The pure fractions were collected and the solvent was evaporated. The residue (0.072g, 50%) was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 0.049g (30%) of compound 5 (M. P.: 178C).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,126053-15-4, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/37308; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 628-13-7, 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 628-13-7 as follows.

EXAMPLE 4 Preparation of 4-cyano-4′-hydroxybiphenyl 1 g of p-(4-methoxyphenyl)benzonitrile and 3 g of pyridium chloride are introduced under nitrogen into a 50 ml two-necked flask. The mixture is heated at 200 C. for 6 hours then it is left to cool down. 5 ml of pyridine and 5 ml of 1 N hydrochloric acid are poured in at 110 C. The reaction mixture is extracted with chloroform at ambient temperature. The organic phases are collected and washed with water, (2*30 ml), dried over anhydrous magnesium sulphate and concentrated under vacuum. After recrystallization from an ethyl acetate/heptane mixture, the sought product is obtained (yield: 50%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,628-13-7, its application will become more common.

Reference:
Patent; Societe d’Expansion Scientifique Expansia; US6046352; (2000); A;,
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. 18368-63-3, name is 2-Chloro-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 18368-63-3

Example 92-((1H-indol-3-yl)methyl)-9-(6-methylpyridin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one a) 9-(6-methylpyridin-2-yl)-2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one; The mixture of 2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one (50 mg, 0.077 mmol, contains 1.7 moleq TFA), 2-chloro-6-methylpyridine (13 mul, 0.116 mmol), Pd2 dba3 (3.6 mg, 3.9 mumol), sodium t-butanolate (22.3 mg, 0.23 mmol), 2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline (DavePhos, 3.1 mg, 7.8 mumol) and dry dioxane (1 ml) was placed in a microwave tube and flushed with argon. The tube was sealed and the suspension was heated at 100 C. for 1 h under microwave conditions. The reaction mixture was diluted with ethyl acetate and washed with water and brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting brown oil was purified by flash chromatography (EtOAc/hexane 1:1) to yield 34 mg (80%) of the title compound [LCMS RtD=2.85 min, [M+H]+=543.2].

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, 18368-63-3, 2-Chloro-6-methylpyridine.

Reference:
Patent; BADIGER, Sangamesh; BEHNKE, Dirk; BETSCHART, Claudia; COTESTA, Simona; HINTERMANN, Samuel; OFNER, Silvio; PANDIT, Chetan; ROY, Bernard Lucien; US2012/101110; (2012); 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 87407-12-3, name is 3-(Trifluoromethyl)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-(Trifluoromethyl)picolinic acid

Example 122; N- [3- ({2-[ (cyclopropylcarbonyl) amino] imidazo [1, 2-a] pyridin-6- yl}oxy) phenyl] -3- (trifluoromethyl) pyridine-2-carboxamide; To a solution of 3- (trifluoromethyl)pyridine-2-carboxylic acid (47.5 mg, 0.249 mmol) in tetrahydrofuran (5 mL) were addedN,N-dimethylformamide (2 drops) and oxalyl chloride (43.2 muL, 0.498 mmol), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in N,N-dimethylacetamide (6 mL) , and the solution was stirred at room temperature. N- [6- (3- Aminophenoxy) imidazo [1, 2-a]pyridin-2-yl] cyclopropanecarboxamide (66 mg, 0.214 mmol) was added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (0%-?-100% ethyl acetate-hexane) to give the title compound (72.5 mg, 70%) as a white solid. 1H-NMR (DMSO-d6,400 MHz) delta 0.74 – 0.85 (4H, m) , 1.87 – 1.98 (IH, m) , 6.81 (IH, dd, J = 8.3, 2.4 Hz), 7.12 (IH, dd, J = 9.7, 2.3 Hz), 7.32 – 7.40 (2H, m) , 7.48 (IH, d, J = 9.5 Hz), 7.54 (IH, d, J = 8.1 Hz), 7.80 (IH, dd, J = 8.3, 4.9 Hz), 8.07 (IH, s) , 8.38 (IH, d, J = 7.8 Hz), 8.61 (IH, d, J = 2.2 Hz), 8.91 (IH, d, J = 4.4 Hz), 10.78 (IH, s) , 10.99 (IH, s) .

With the rapid development of chemical substances, we look forward to future research findings about 87407-12-3.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/150015; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem