Pyridine-derivatives

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. 13466-43-8, name is 3-Bromopyridin-2(1H)-one, the common compound, a new synthetic route is introduced below. Recommanded Product: 13466-43-8

Methyl iodide (1.5 mL, 24.14 mmol) was added to a suspension of potassium carbonate (1668 mg, 12.07 mmol), TBAI (89 mg, 0.24 mmol) and 3-bromopyridin-2-ol (420 mg,2.4 14 mmol) in toluene (15 mL). The reaction mixture was heated to 40 C for 17 hours. The mixture was partitioned between DCM and water and the combined extracts dried (hydrophobic fit) and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluted with 0-70% petrol/ethyl acetate to afford 3 -bromo- 1- methylpyridin-2(1H)-one, Intermediate 5 (390 mg, 86 %).?H NMR (400 MHz, DMSO-d6) & 3.50 (s, 3 H) 6.17 (t, J=7.07 Hz, 1 H) 7.78 (dd, J=6.82,1.77 Hz, 1 H) 7.90 (dd, J=7.33, 1.77 Hz, 1 H)

The synthetic route of 13466-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LIMITED; LIVERMORE, David; WHITE, Kathryn; CONGREVE, Miles; BROWN, Giles; O’BRIEN, Michael; WO2014/122474; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22245-83-6, 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. 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol. A new synthetic method of this compound is introduced below.

EXAMPLE 12APreparation of compound 2003Step 1 :To a mixture of 2-hydroxy-3-triotafluoromethylpyridine 12a1 (39.01 g, 239 mmol) and anhydrous DMF (800 ml_) under Ar is added lambda/-iodosuccinimiotade (4.89 g, 244 mmol) and anhydrous K2CO3 (33.72 g, 244 mmol) and the mixture is allowed to stir at 600C for about 3 hours. The mixture is cooled to ambient temperature, filtered and concentrated under reduced pressure. The residue is dissolved in DCM (1 L) and the organic phase is washed with brine The aqueous phase is adjusted to pH 4 by the addition of 2 M HCI then extracted with DCM (1 L). The combined organic extracts are washed with brine (2 L) and dried over Na2SO4 The mixture is concentrated to ~300 mL and cooled overnight in a fridge. The precipitated solid is removed by filtration and dried to provide aryl iodide 12a2

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22245-83-6, 3-(Trifluoromethyl)pyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/18657; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 145100-50-1, 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. 145100-50-1, name is 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide, molecular formula is C7H4F6N2O4S2, 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.

At -78C, a solution of tert-butyl 4-oxo-3 ,4-dihydro-2//-spiro[naphthalene- 1 ,4′- piperidine]-l’-carboxylate (Al) (2.66g, 8.44 mmol) in THF (30 ml) was added dropwise to a solution of lithium bis(trimethylsilyl) amide (1.0M in hexane, 10.5 ml, 10.5 mmol) in THF (20 ml). After 30 min at -78C, 2-(N,N-bis(trifluoromethylsulfonyl)amino)-pyridine (3.77g, 10.5 mmol) was added and the reaction mixture was slowly warmed to 00C (ca. 2h), poured into ice, extracted with ether, and purified by flash chromatography on silica gel(hexane/dichloromethane 8:2) to give tert-butyl 4-(trifluoromethylsulfonyloxy)-2H- spiro[naphthalene-l,4′-piperidine]-l’-carboxylate (A2). LC-MS: m/e = 391.9 (M + H – C(CH3)3). Rt= 4.19 min. 1H-NMR (500MHz, DMSO-d6): 7.50 (d, IH)3 7.40 (t, IH), 7.30 (t, IH), 6.16 (t, IH), 3.83 (br.d, 2H), 3.05 (br. s, 2H), 2.67 (d, 2H), 1.72 – 1.67 (m, 4H), 1.41 (s, 9H). [00147] A mixture of the triflate (A2) (447 mg, lmmol), sodium cyanide (lOOmg, 2 mmol), copper (I) iodide (19 mg, 0.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) in acetonitrile (10 ml) was degassed and heated under reflux under nitrogen for 4h. After concentration, the residue was directly purified by flash chromatography (hexane/EtOAc 8:2) to give tert-butyl 4-cyano-2H-spiro[naphthalene-l,4′-piperidine]-r-carboxylate (A3) (300 mg). LC-MS: m/e = 269.0 (M + H – C(CH3)3. 3.75 min. 1H-NMR (500MHz5 DMSOd6): 7.49 (d, 1 H), 7.42 – 7.36 (m, 3H), 7.09 (t, IH), 3.81 (br. d, 2 H), 3.03 (br. s, 2H), 2.67 (d, 2H), 1.70 (td, 2H), 1.62 (d, 2H), 1.41 (s, 9H),[00148] A solution of the m’trile (A3) (300 mg) in dichloromethane (3 ml) was treated with TFA (1 ml) for 1 hour, concentrated, co-evaporated with acetonitrile and dissolved in dichloromethane (ca. 100ml). The resulting solution was washed with a mixture of brine (ca. 20 ml) and 6N NaOH (2 ml), dried over Na2SO4, and concentrated to give 2H-spiro[naphthalene- l,4′-piperidine]-4-carbonitrile (A4) as a white solid. LC-MS: m/e = 225.2 (M + H). R,= 1.53 min.

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 145100-50-1, 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/5295; (2008); A2;,
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 13958-98-0, name is 3-Bromo-4-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 13958-98-0

Step A: Preparation of 2-phenylthieno[2,3-c]pyridin-3-amine: A mixture of benzyl mercaptan (0.2719 g, 2.19 mmol, 1.0 equiv.) and DMF (3 mL) was stirred at room temperature, and NaOMe (250 mg, 2.1 equiv) was added. The solution was stirred for 5 minutes, and then 3-bromoisonicotinonitrile (400 mg, 1.0 equiv.) was added directly to the solution. The reaction mixture was stirred overnight at room temperature, then the volatiles were removed via rotary evaporation. Water was added, and the reaction mixture was extracted twice with ether. The combined organic layers were dried (Na2SO4) and purified by silica gel chromatography (eluting first with 100% Et2O to remove non-polar impurities, then switching to a CHCl3/MeOH gradient) to afford 221 mg (45%) of the desired product.

With the rapid development of chemical substances, we look forward to future research findings about 13958-98-0.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 117519-08-1, Adding some certain compound to certain chemical reactions, such as: 117519-08-1, name is 2-Chloro-3-nitro-6-(trifluoromethyl)pyridine,molecular formula is C6H2ClF3N2O2, 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 117519-08-1.

A solution of 2-chioro-3-nitro-6-(trifiuoromethyl)pyridine (2.0 g, 8.8 mmoi) and 6-aninobenzo[d]thiazoi-2(3H?)-one (1.5 g, 8.8 mmol) in DMF (40 ml.) was heated at 110 0Q After 3h. sodium dithionite (6.1 g, 35.3 mmoi) was added to the mixture was let stir at 110 cc for 5 h. Thereaction was diluted with water (320 mL) and let stir for 20 mm where precipitate formed. Thereaction was filtered and the solid was washed with H20 and oven dried at 45 C to give the desiredcompound as a solid (2.6 g, 90%). MS (ESI): mass caicd. for C,3HF3N4OS, 326.05 rn/z found, 327.0 [M++{]t.

According to the analysis of related databases, 117519-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73583-37-6 ,Some common heterocyclic compound, 73583-37-6, molecular formula is C5H3BrClN, 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 stirring solution of 4-bromo-2-chloropyridine (2.0 g, 10.39 mmol) in diethyl ether (30 mL) at -70 C under nitrogen was added n- butyllithium, 2.5 M solution in hexanes (4.57 mL, 11.43 mmol) at a rate not to exceed -65 C. A white precipitate had formed. After 5 min a solution of cyclopropyl methyl ketone (Lancaster Synthesis, Ltd., 1.030 mL, 10.39 mmol) in diethyl ether (5 mL) was added to the suspension. After 5 min the cooling bath was removed and warmed to -15 C. The suspension was then quenched with saturated NH4C1 (15 mL) and EtOAc (20 mL) added. The separated organic was then dried over MgSC^, concentrated under reduced pressure, then purified by silica gel chromatography (80 g) eluting products with 10 to 30% gradient of EtO Ac/Hex to afford l-(2-chloro-4-pyridinyl)-l-cyclopropylethanol (1.35 g, 6.83 mmol, 65.7 % yield) as amber oil (mixture of 2 enantiomers).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73583-37-6, its application will become more common.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 108-99-6, 3-Methylpyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

General procedure: In an oven dried glass tube containing a mixture of pyridine 1a (100 mg, 1.26 mmol), and potassium persulphate (683 mg, 2.53 mmol), formamide 2a (2 ml) was added and the reaction mixture was heated at 70 C. Upon the completion of the reaction (monitored by TLC), saturated sodium bicarbonate solution (5 mL) was added and the crude product was extracted in ethyl acetate (3 X 5 mL). The crude product was purified by column chromatography to furnish compound 3aa as a white crystalline solid (122 mg, 79% yield)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108-99-6, 3-Methylpyridine, and friends who are interested can also refer to it.

Reference:
Article; Mete, Trimbak B.; Singh, Ankit; Bhat, Ramakrishna G.; Tetrahedron Letters; vol. 58; 50; (2017); p. 4709 – 4712;,
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. 20265-35-4, name is 2-Methoxy-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6N2O3

Method 4 Synthesis of 7-methoxy-1H-pyrrolo[2,3-c]pyridine (Intermediate 5) A solution of R-4 (500 mg, 3.24 mmol) in anhydrous THF (20 mL) is cooled to -78° C. and vinylmagnesium bromide (9.73 mL of a 1 M solution in THF, 9.73 mmol) added. The reaction is stirred at -20° C. for 6 h then quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic phase is concentrated in vacuo and the crude material purified by flash chromatography (SiO2, 2percent to 10percent MeOH in DCM) to give the title intermediate I-5 (100 mg) m/z 148.9 [M+H].

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, 20265-35-4, 2-Methoxy-3-nitropyridine.

Reference:
Patent; BARTOLOZZI, Alessandra; CHEN, Zhidong; DINES, Jonathon Alan; LO, Ho Yin; LOKE, Pui Leng; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee M.; US2013/196967; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 86604-79-7, 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 86604-79-7, name is 2,3,5-Trimethyl-4-nitropyridine 1-oxide. This compound has unique chemical properties. The synthetic route is as follows.

The 2,3,5-trimethyl-4-nitropyridine1-oxide (13.4 g, 73.6 mmol) obtained in the step (11c) was added to acetyl chloride (80 ml, 1,125 mmol) at -30 C. in a nitrogen atmosphere. The mixture was stirred at -30 C. to room temperature for 4 hours and 20 minutes. After the reaction mixture was concentrated, the residue was subjected to silica gel column chromatography (NH silica gel: 300 g, elution solvent: heptane, heptane/ethyl acetate=50/50, ethyl acetate, ethyl acetate/methanol=10/1) to obtain fractions containing a pure product of the title compound and fractions containing a crude product of the title compound. The fractions containing a crude product of the title compound was concentrated. The residue was suspended in ethyl acetate and the resulting precipitate was collected by filtration, washed with ethyl acetate and diethyl ether to obtain the title compound (Lot A, 1.58 g) as a white solid. The filtrate was concentrated. The residue was dissolved in chloroform and washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was suspended in diethyl ether. The resulting precipitate was collected by filtration, washed with diethyl ether to obtain the title compound (Lot B, 2.69 g) as a pale brown solid. The fractions containing a pure product of the title compound were concentrated. The residue was dissolved in chloroform, washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous sodium sulfate, filtered and concentrated to obtain the title compound (Lot C, 6.56 g) as a pale white solid. The yield of the obtained title compounds of 3 lots was 85.7% in total. Lot A: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s). Lot B: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s). Lot C: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s).

According to the analysis of related databases, 86604-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; US2007/10542; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65515-32-4 ,Some common heterocyclic compound, 65515-32-4, molecular formula is C8H8ClNO3, 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-2-methoxy-nicotinic acid methyl ester (18.5.0 g, 0.092 mol) in 50 mL of NMP was added p-methoxybenzylamine (19.0 g, 0.14 mol) and triethylamine (10.Og, 0.1 mol). The mixture was heated to 70 0C for 4 h, cooled and diluted with water and extracted with ethyl acetate, washed with water, brine, dried with sodium sulfate, and evaporated to get an oil which was precipitated with ethylacetate/hexane mixture (1 :1). This was then filtered and dried to yield 15 g (60 %) of the target compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65515-32-4, its application will become more common.

Reference:
Patent; SCIOS, INC.; WO2006/112828; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem