Category: pyridine-derivatives

Related Products of 73781-91-6, Adding some certain compound to certain chemical reactions, such as: 73781-91-6, name is Methyl 6-chloronicotinate,molecular formula is C7H6ClNO2, 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 73781-91-6.

To a suspension of sodium hydride (55% dispersion in mineral oil, 852 mg, 20 mmol) in THF (27 mL) was added a solution of [3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (3.68 g, 18 mmol) in THF (54 mL) at 0 C. and the reaction mixture warmed to room temperature over 30 min. Then a solution of methyl 6-chloronicotinate (3.35 g, 20 mmol) in THF (1.5 mL) was added dropwise at 0 C. and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and brine and then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=7:3) afforded the title compound (4.1 g, 68%) which was obtained as a white solid. MS: m/e=343.1 [M+H]+.

According to the analysis of related databases, 73781-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Buettelmann, Bernd; Jakob-Roetne, Roland; Knust, Henner; Lucas, Matthew C.; Thomas, Andrew; US2009/143371; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1187190-69-7 , The common heterocyclic compound, 1187190-69-7, name is 6-Chloro-4-methoxynicotinonitrile, molecular formula is C7H5ClN2O, 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.

General procedure: General Procedure: An oven-dried test tube equippedwith a magnetic stir bar was charged with 2-chloroisonicotinonitrile (69 mg,0.5 mmol), Pd(OAc)2 (2.25 mg, 2 mol%), BINAP (9.38 mg, 3 mol%) , theamine if solid (1.0 mmol), and Cs2CO3 (228 mg, 1.0 mmol).The vessel was then sealed, evacuated, and backfilled with argon (this sequencewas carried out a total of three times). 1,4-dioxane (2.0 mL) and the amine ifliquid (1.0 mmol) via syringe was added successively under an argon atmosphere., and the solution was heated up to 80C for 4 h in an oil bath. The reactionmixture was allowed to cool to r.t. diluted with dichloromethane, and washed once each withwater and brine, dried over Mg2SO4, filtered, andconcentrated in vacuo. The crude product was then purified by silicagelchromatography mixture of pentane and Et2O or mixture of pentane andethyl acetate. The products were characterized by 1H NMR, 13CNMR and LC-MS.

The synthetic route of 1187190-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Shuo; Wang, Yaping; Sun, Chunxia; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Tetrahedron Letters; vol. 54; 25; (2013); p. 3233 – 3237;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-14-1 ,Some common heterocyclic compound, 884495-14-1, molecular formula is C7H7BrN2O3, 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.

DMF-DMA (600 mL) was slowly added to a stirred and heated (80 C) solution of 5-bromo-2- methoxy-4-methyl-3-nitropyridine (134 g, 0.54 mol) in DMF (1.1 L). After addition, the mixture was heated at 95 C for 5 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled to room temperature and poured into ice-cold water (3 L). The resulting red solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (167 g, 100% yield) as red solid. 1H NMR (400 MHz, DMSO-d6): 6 8.24 (s, 1 H), 7.05 (d, J= 13.6 Hz, I H), 7.05 (d, J= 13.6 Hz, 1 H), 4.80 (d, J = 13.2 Hz, 1 H), 3.88 (s, 3 H), 2.90 (s, 6 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-14-1, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HEWITT, Michael, Charles; HSIAO-WEI TSUI, Vickie; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (128 pag.)WO2016/77380; (2016); 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. 55240-51-2, name is 2-Phenylisonicotinic acid. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

2-phenyl-4-carboxypyridine (3 g, 15 mmol) was refluxed overnight in MeOH (70 ml) and H2SO4 (4 ml). After evaporation of the solvent, water (100 ml) was added and the mixture was neutralized with saturated NaHCO3 solution. The aqueous phase was then extracted with CH2Cl2 (2×100 ml). The combined organic fractions were washed with water (100 ml), brine (50 ml) and dried over MgSO4. The crude compound was then flash chromatographed (SiO2, CH2Cl2) to afford 2.3 g (72%) of the titled compound as a colourless oil.

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, 55240-51-2, 2-Phenylisonicotinic acid.

Reference:
Patent; KONINKLIJKE PHILIPS ELECTRONICS N.V.; WO2007/4113; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10592-27-5 ,Some common heterocyclic compound, 10592-27-5, molecular formula is C7H8N2, 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.

Step 2; A solution of Br2 (2.78 ml, 8.64 g, 54 mmole) in dry dichloromethane (40 ml) was added dropwise over a period of 1 h 45 min to a stirred and cooled (-10C) solution of 2.3-dihydro-1H-pyrrolo[2,3-b]pyridine (6.5 g,54 mmole) in a mixture of dry dichloromethane (60 ml) and pyridine (6 ml). The suspension was stirred at 0C for 2 hrs, poured into a mixture of NaHCO3 (120 ml) and saturated aqueous Na2S2O3 (15 ml) and extracted with a solution of ethyl acetate/methanol (3X200 ml). The organic layers were concentrated to afford 3.7 g of 5-bromo- 2,3-dihydro- 1H-pyrrolo[2,3-b]pyridine (2) after purification by flash chromatography using dichloromethane as eluent (35% yield). 1H NMR (400 MHz, DMSO-D6) delta ppm 2.98 ( t, J = 8.54 Hz, 2H ) 3.48 (t, J=8.55 Hz, 2H) 6.58 (bs, 1 H) 7.37(s,1 H) 7.71 (s,1 H)

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. 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; EP2070928; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5470-70-2, 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. 5470-70-2, name is Methyl 6-methylnicotinate. A new synthetic method of this compound is introduced below.

0.471 g (1.0 equivalent) of N-bromosuccinimide and 64 mg (0.1 equivalent) of benzoyl peroxide are added to a solution of 0.4 g of the product obtained in the preceding Stage 1 in 15 ml of carbon tetrachloride. The solution is brought to reflux for 6 hours, then filtered and evaporated under reduced pressure. The residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate: 95/5) to produce 0.262 g of the expected product. [ Yield: 43% MS: MH+ 231

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5470-70-2, Methyl 6-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Dublanchet, Anne-Claude; Compere, Delphine; Cluzeau, Philippe; Blais, Stephane; Denis, Alexis; Ducrot, Pierre; Courte, Karine; Descamps, Sophie; US2004/72871; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 4548-45-2, 2-Chloro-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, 4548-45-2, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-nitropyridine

To a stirring solution of compound 20 (5.0 g, 31.5 mmol) in acetic acid (50 ml) was added iron powder (8.8 g, 157.6 mmol) in small portion at room temperature, the reaction was exothermic and the temperature rise to 80C, end of added and kept the temperature at 40-50C and stirred for 2h. The reaction was filtered through celite and washed with little acetic acid, the filtrate was evaporated to dryness, adjusted pH=8 with saturated solution of sodium bicarbonate, extracted with dichloromethane (100 ml x 5). The combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated to afford crude compound 84 (3.9 g, yield 96%) as a brown solid, used directly in next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4548-45-2, its application will become more common.

Reference:
Patent; SHANGHAI DE NOVO PHARMATECH CO LTD.; GAO, Daxin; YANG, Heping; YU, Yajun; WO2013/91502; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16133-25-8, Pyridine-3-sulfonyl chloride, 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, COA of Formula: C5H4ClNO2S, blongs to pyridine-derivatives compound. COA of Formula: C5H4ClNO2S

4-(a) tert-Butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate To 14 ml of a methylene chloride solution containing 640 mg (3.60 mmol) of 3-pyridylsulfonyl chloride were added 1.20 g (3.56 mmol) oftert-butyl [(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate obtained by the same manner as in Reference example 1-(e) and 2.24 ml (16.2 mmol) of triethylamine, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, to the reaction mixture was added a 5percent aqueous potassium hydrogen sulfate solution, and the mixture was extracted with chloroform. The organic layer was successively washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1–>1:2 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 1.45 g of the title compound as colorless oil. (Yield: 85percent) Mass spectrum (CI, m/z): 479 (M++1). 1H-NMR spectrum (CDCl3, delta ppm): 9.06 (d, J=2.2 Hz, 1H), 8.71 (dd, J=4.6, 1.5 Hz, 1H), 8.13-8.08 (m, 1H), 7.68 (d, J=8.2 Hz, 1H), 7.52 (dd, J=8.2, 7.4 Hz, 1H), 7.38-7.32 (m, 1H), 6.77 (d, J=7.4 Hz, 1H), 5.80 (t, J=5.1 Hz, 1H), 4.40 (s, 2H), 4.24 (d, J=5.1 Hz, 2H), 1.53 (s, 9H), 1.46 (s, 9H).

The synthetic route of 16133-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; EP2476678; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63071-10-3, (4-Chloropyridin-2-yl)methanol, 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, HPLC of Formula: C6H6ClNO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H6ClNO

Example 307 Synthesis of (4-chloropyridin-2-yl)methyl 4-methylbenzenesulfonate. Sodium hydride (44 g, 60%, 1.096 mol) was added to a cooled (0 C.) solution of (4-chloropyridin-2-yl)methanol (80 g, 548 mmol) in THF (1500 mL) at 0 C. The mixture was stirred at 0 C. for 1 h, and tosyl chloride (104 g, 548 mmol) was added. After stirring at 0 C. for another 3 h, the mixture was quenched with H2O (50 mL), and extracted with ethyl acetate (120 mL*3), the combined organic layers were washed with brine, dried over with anhydrous magnesium sulphate, filtered, and concentrated to afford (4-chloropyridin-2-yl)methyl 4-methylbenzenesulfonate (162 g, crude) as a brown oil which was used in the next step without purification. ESI-MS [M+H]+: 296.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63071-10-3, (4-Chloropyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.53636-56-9, name is Methyl 3-bromo-2-pyridinecarboxylate, molecular formula is C7H6BrNO2, molecular weight is 216.03, as common compound, the synthetic route is as follows.COA of Formula: C7H6BrNO2

N-((4-chloro-2-methylphenyl)(phenyl)methyl)-2-(2-(2-(hydroxymethyl)pyridin-3-yl)benzofuran-5- yl)acetamidea) (3-bromopyridin-2-yl)methanolTo a solution of methyl 3-bromopicolinate (1 g, 4.6 mmol) in MeOH (50 mL) at 0 C was added NaBH4 (883 mg, 23.2 mmol). The reaction mixture was stirred at rt overnight, followed by concentration under reduced pressure. The resultant residue was dissolved in EtOAc (50 mL), washed with aq. NH4C1 (3 x 20 mL), dried over Na2S04, filtered, and concentrated to afford the title compound (101 g, 92%) as a white solid. LCMS-P 1 : 190/192 [M+H]+; Rt: 1.070 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53636-56-9, Methyl 3-bromo-2-pyridinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; BOHNERT, Gary, J.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; SUNG, Leonard; WO2013/19682; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem