Tag: M.W:200-300

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.1155847-42-9, name is 2-Bromo-4-chloro-3-fluoropyridine, molecular formula is C5H2BrClFN, molecular weight is 210.43, as common compound, the synthetic route is as follows.Recommanded Product: 2-Bromo-4-chloro-3-fluoropyridine

To a degassed solution of 2-bromo-4-chloro-3-fluoropyridine (7.3g, 34.7 mmol) in DMF (50 mL) was added palladium tetrakistriphenylphosphine (4.01g, 3.47 mmol) and zinc cyanide (4.07g, 34.7 mmol) and heated to 1000C for 20 minutes. After this time, more palldium tetrakis triphenylphosphine (4.01g, 3.47mmol) was added and heated to 100C for 90 minutes. The mixture was allowed to cool to room temperature and treated with water (200 mL) and ether (400 mL). The resulting mixture was filtered to remove insoluble solids, the filtrate was partitioned, and the aqueous layer was extracted with ether (400 mL). The combined ether extracts were washed with water (200 mL), dried (MgSO4), filtered, and the solvent removed in vacuo. This residue was purified by chromatography using silica gel column (330 g) eluting with a gradient of 10-100% CH2CI2 in hexanes to provide the title compound. lH NMR (CDCI3) delta=8.45 (d, IH, J=5Hz) and 7.65 (dd, IH, J=5Hz) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1155847-42-9, 2-Bromo-4-chloro-3-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/67166; (2009); A2;,
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. 1190862-70-4, name is Ethyl 5-bromo-6-methylnicotinate, the common compound, a new synthetic route is introduced below. Recommanded Product: Ethyl 5-bromo-6-methylnicotinate

Ethyl 5-bromo-6-methyl-pyridine-3-carboxylate (1 g, 4.1 mmol) was dissolved in heavy water (10 mL).Deuterated sodium hydroxide (1.51 g, 14.75 mmol) was added thereto, and the reaction solution was heated to 140 C overnight.After the reaction was completed, it was cooled to room temperature, and the pH was adjusted to 3-4 with a 2N aqueous HCl solution, and the precipitated solid was filtered, washed with a small amount of water, and dried.A white solid 784 mg was obtained.

The synthetic route of 1190862-70-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceutical Group Co., Ltd.; Wan Huixin; Li Chunli; Shi Chen; Liu Haiyan; Li Ping; Shen Jingkang; (50 pag.)CN104341425; (2018); B;,
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. 280566-45-2, name is 2-Chloro-6-(trifluoromethyl)nicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

In a vial, 2-chloro-6-(trifluoromethyl)nicotinic acid (0.98 g, 4.4 mmol) and 2- chloro-6-(trifluoromethyl)isonicotinic acid (1.85 g, 8.2 mmol) were dissolved in ethyl orthoformate (5.0 mL, 30.1 mmol) and heated at 120 C for 5 hours at which time TLC analysis showed that most of the starting material had been consumed and the products were formed. The reaction mixture was evaporated in vacuo and the residue was purified by silica gel chromatography using 10% EtOAc/hexanes to give the two ethyl ester products. ? NMR (400 MHz, CDC13): delta 8.14 (s, 1 H), 8.08 (s, 1 H), 4.47 (q, 2H), 1 .44 (t, 3H).

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, 280566-45-2, 2-Chloro-6-(trifluoromethyl)nicotinic acid.

Reference:
Patent; INCYTE CORPORATION; RODGERS, James D.; ARVANITIS, Argyrios G.; WO2013/26025; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 223463-13-6, Adding some certain compound to certain chemical reactions, such as: 223463-13-6, name is 5-Bromo-2-iodopyridine,molecular formula is C5H3BrIN, 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 223463-13-6.

Example 1 : Preparation of 5-bromo-pyridine-2-sulfonic acid picolyl amideAt O0C, a solution of isopropylmagnesiumchoride (2 M in tetrahydrofuran, 1.1 equivalents (eq.)) was slowly added to 80 mmol of 3-bromo-6-iodo-pyridine in 80 ml of tetrahydrofuran, maintaining the temperature between 0 and 1 O0C. After stirring for 1 h at about 2O0C, the solution was cooled to (-4O)0C. Then, 2.5 eq. of SO2 was added under intense cooling to maintain a temperature of (-4O)0C. After 30 minutes at this temperature, 1.1 eq. of SO2CI2 was added carefully. Then, the reaction mixture was warmed to O0C. After 30 minutes stirring, 10 % aqueous hydrochloric acid was added carefully. Then, the crude reaction mixture was extracted with 100 ml of diethyl ether three times. The combined organic phases were washed with saturated aqueous sodium chloride and then dried over sodium sulfate. The solvent was removed and the crude sulfochloride was dissolved in 40 ml of acetonitrile.Meanwhile, 1.1 equivalent of picolylamine and 1.1 equivalent of triethylamine were dissolved in 50 ml of methylcyanide and cooled to O0C. The crude sulfochloride in methylcyanide was added via a dropping funnel maintaining the temperature below 100C. The solution was warmed to about 2O0C and stirred over night. Then, the precipitated solid was filtered off and washed with 30 ml of water. The product obtained was an off-white solid. Yield: 20.0 g (82 %); m.p.: 1560C.

According to the analysis of related databases, 223463-13-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2007/93599; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 670253-37-9, 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 670253-37-9 as follows.

Zinc cyanide (0.254 g, 2.17 mmol) and tetrakistriphenylphosphine palladium (0) (0.460 g, 0.394 mmol) were added to a solution of compound 30 (1.00 g, 3.94 mmol) in N-methylpyrrolidinone (10 mL). The reaction mixture was heated under N2(g) to 135 C for 2 h, cooled to room temperature and partitioned between EtOAc (30 mL) and aqueous ammonia solution (0.35%, 50 mL). The organic fraction was separated, washed successively with water (2 × 100 mL) and brine (30 mL), dried (MgSO4) and reduced in vacuo onto SiO2. Column chromatography (SiO2), eluting with 2:1 Petrol-EtOAc to 1:1 Petrol-EtOAc, afforded the title compound16 (0.360 g, 2.35 mmol, 60%) as an off-white solid, m.p. 216-219 C (from EtOH-water); Rf 0.23 (1:1 Petrol-EtOAc); deltaH (300 MHz, DMSO-d6); 8.39 (1H, s, 2-H), 7.38 (2H, br s, 6-NH2), 6.62 (1H, s, 5-H); deltaC (75 MHz, DMSO-d6); 162.7 (6-C), 155.3 (2-C), 143.8 (4-C), 116.6 (3-C), 107.5 (5-C), 95.9 (3-CN); numax/cm-1 (solid); 3424, 3331, 3118, 2224, 1656 and 1591; m/z (EI) 153.0 (100%, M+); (Found M+, 153.0095. C6H4ClN3 requires M 153.0094); LC-MS; RT= 1.32min, m/z (ES+) found MH+, 154.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,670253-37-9, its application will become more common.

Reference:
Article; Yule, Ian A.; Czaplewski, Lloyd G.; Pommier, Stephanie; Davies, David T.; Narramore, Sarah K.; Fishwick, Colin W.G.; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 31 – 38;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 166266-19-9 , The common heterocyclic compound, 166266-19-9, name is 5-Iodo-3-methylpyridin-2-amine, molecular formula is C6H7IN2, 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.

Sodium nitrite (0.708 g, 10.25 mmol) was added to a mixture of 5-iodo-3-methyl-pyridin-2- ylamine (2 g, 8.55 mmol) and H2504 (12 mL) at 0 C. The reactiom mixture was stirred 15 mm at 60C, allowed to cool down, and poured onto crushed ice. Boric acid (1.057 g, 17.09 mmol) was added and the solution was quickly heated to 100 C. The reaction mixture was cooled down and neutralized with a saturated aq. NH4OH solution. The suspension was filtered toafford the crude title product (1.67 g, 7.11 mmol, 83% yield) as a brown solid. tR: 2.85 mm (H PLC 1); tR: 0.62 mm (LC-MS 2); ESl-MS: 236 [M+H] (LC-MS 2).

The synthetic route of 166266-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; WO2014/191896; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 139163-56-7, Adding some certain compound to certain chemical reactions, such as: 139163-56-7, name is 1-(6-Bromopyridin-2-yl)ethanol,molecular formula is C7H8BrNO, 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 139163-56-7.

Intermediate 17-1 Methyl 6-(1-hydroxyethyl)pyridine-2-carboxylate (1339) (1340) 2.00 g of 1-(6-bromopyridin-2-yl)ethanol (Telfer, Shane G.; Kuroda, Reiko, Chemistry A European Journal, 2005, 11, 57-68) were suspended in 20 ml of methanol and 30 ml of dimethyl sulphoxide. 265 mg of 1,3-bis(diphenylphoshino)propane, 140 mg of palladium(II) acetate and 3.2 ml of triethylamine were added, the mixture was flushed three times with carbon monoxide and stirred in a carbon monoxide atmosphere (12 bar 0.5 h, then at 16 bar overnight). Water was added, the mixture was extracted with ethyl acetate and the extract was concentrated. This gave 1.7 g of methyl 6-(1-hydroxyethyl)pyridine-2-carboxylate as an oil (crude product). (1341) 1H-NMR (400 MHz, CHLOROFORM-d): delta=1.57 (d, 3H), 4.02 (s, 3H), 5.03 (q, 1H), 7.56 (d, 1H), 7.88 (t, 1H), 8.05 (d, 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. 139163-56-7, 1-(6-Bromopyridin-2-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BOTHE, Ulrich; SIEBENEICHER, Holger; SCHMIDT, Nicole; ROTGERI, Andrea; BOeMER, Ulf; RING, Sven; IRLBACHER, Horst; GUeNTHER, Judith; STEUBER, Holger; LANGE, Martin; SCHAeFER, Martina; (191 pag.)US2016/311833; (2016); 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. 1440519-73-2, name is 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, molecular formula is C15H13ClN2O2, 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: 1440519-73-2

To a solution of 2-chloro-6-(4-methoxy-benzyl)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one (5.8 g, 20.0 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 1.7 g, 42.0 mmol) at room temperature. The resulting reaction mixture was stirred for 30 min before iodomethane (6.0 g, 42.0 mmol) was added. After stirring at room temperature over night, the mixture was quenched with water and extracted with EtOAc. The organic layer was then washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give the crude product which was then purified by flash column chromatography (silica gel 20 g, 5% to 20% ethyl acetate in DCM). The title compound was obtained (3.8 g, 57%) as a white solid. MS: 316.2 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 1440519-73-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-chloro-4-methoxypyridine

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 C for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product. 1H NMR (500 MHz, DMSO- , 5 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC MS (M+l)+ – 169.

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, 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; PASTERNAK, Alexander; SHI, Zhi-Cai; CATO, Brian; KIM, Esther, Y.; WO2013/66718; (2013); 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 62150-47-4, name is Ethyl 4-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H8BrNO2

To a stirring solution of compound 2.3 (32.4 g,. 0.14 mol). compound 2,4 (32.2 g, 0.17 mol) and Pd(PPh2)4 (8.08 g, 7 ram of) in 1 ,4-dioxane/nrietrianoi (800 rnL 1 :1) was added Na2COs (22.3 g,u.21 mol) under an argon atmosphere and the mixture was stirred at 80C for 15 nr. The solvent was removed under reduced pressure and the resulting residue was diluted with wafer (500 rnL) and extracted with EtOAc (3 x 500 ml). The combined organic layers were dried and concentrated under reduced pressure to give a crude, which was purified by flash chromatography (silica gel/ RhoEpsilon.Alpha 2: 1) to give ethyl 4-(4-formylphenyl picolinate (2.5, 14.2 g, 40%) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 62150-47-4.

Reference:
Patent; ACHAOGEN, INC.; PATTERSON, Brian D.; LU, Qing; AGGEN, James Bradley; DOZZO, Paola; KASAR, Ramesh Annasaheb; LINSELL, Martin Sheringham; KANE, Timothy Robert; GLIEDT, Micah James; HILDEBRANDT, Darin James; MCENROE, Glenn A.; COHEN, Frederick; WO2013/170165; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem