Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 24484-98-8, 4-Chloropyridine-2,3-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, COA of Formula: C5H6ClN3, blongs to pyridine-derivatives compound. COA of Formula: C5H6ClN3

Intermediate 8 (700mg, 4.876 mmol), polyphosphoric acid (5 g) and HOAc (442 mg, 7.31 mmol) are heated at 1500C for one hour. The reaction is dissolved in water, then NaOH is added until the pH is adjusted to pH=13. The solution is extracted with ethyl acetate (2×150 mL), washed with K2CO3 solution and brine, dried, and evaporated to give crude 7-chloro-2-methyl- 3H-imidazo[4,5-b]pyridine (9), which is used without purification. 1H NMR 400 MHz (CDCl3) delta 8.14 (s, IH), 6.55 (m, 2H), 2.69 (s, 3H); MS m/z 168.00 (M + 1).

The synthetic route of 24484-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/144253; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256791-13-5, 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. 1256791-13-5, name is 1-(6-Chloro-5-methylpyridin-3-yl)ethanone, molecular formula is C8H8ClNO, 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.

To a mixture of compound l-(6-chloro-5-methyl-3-pyridyl)ethanone (850 mg), compound l-(3,5- dichloro-phenyl)-2,2,2-trifluoro-ethanone (1.82 g) and K2C03 (862mg) in 20 ml of dichloroethane was added Et3N (50 mg). The mixture was refluxed for 16 h. After cooling to 0C, Bu4N+Br” (322 mg), NH2OH.HCl (690 mg, 10 mmol) and NaOH (800 mg, 4 N) was added and the reaction mixture was stirred at room temperature for 16 h. Then, the reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate three times. The combined organic layers were dried over MgS04 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give the title compound (1.6 g). lU NMR (300Mz, DMSO-d6): delta 2.39 (s, 3H), 4.37 (d, 1H), 4.43 (d, 1H), 7.62 (s, 2H), 7.83 (s, 1H), 8.17 (s, 1H), 8.55 (s, 1H).

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 1256791-13-5, 1-(6-Chloro-5-methylpyridin-3-yl)ethanone.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CASSAYRE, Jerome Yves; EL QACEMI, Myriem; LUKSCH, Torsten; RENOLD, Peter; WO2012/156400; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100848-70-2, 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. 100848-70-2, name is 2-Methoxy-4-methylpyridine, molecular formula is C7H9NO, 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.

Ammonia was condensed into a round bottomed flask. While cooling the liquid ammonia with a CO2/acetonebath, NaNH2 (1.73 g) was added quickly. Then, 2-methoxy-4-methylpyridine (5.02 g) was added slowly via a syringe inthe course of 5 min. The reaction mixture turned yellow immediately, but the starting material seemed to precipitate.The cooling bath was removed, and after 20 min, the reaction mixture had turned deep brown. The cooling bath wasput in place again, and sodium 2-chloroacetate (4.74 g) was added portionwise in the course of 5 min. After stirring for35 min, the cooling bath was removed; the reaction mixture had solidified partly. 50 min later, the reaction mixture wasstirring again, and after another 40 min, NH4Cl (3.29 g) was added carefully. The turbid, light brown reaction mixtureimmediately turned clear and yellow. The mixture was left stirring at RT overnight to allow the ammonia to evaporate.To the pasty residue, water (50 ml) was added to give a turbid, yellowish mixture. The pH of the mixture was adjustedto ?4 using 3M aqueous HCl; at first, a white precipitate formed, followed by dark grey lumps. The mixture was extractedwith DCM (2 x 50 mL), the combined extract was washed with brine (50 ml), dried over sodium sulfate, and concentratedin vacuo. The residue was taken up with 1M aqueous NaOH (50 ml), and washed with diethyl ether (50 ml). The basicaqueous layer was adjusted to pH ?4-5 using 3M HCl (aq), and extracted with DCM (2 x 25 ml). Then, the pH wasadjusted to pH ?3-4, and the aqueous layer was extracted again with DCM (2 x 25 ml). The combined organic layer wasdried over sodium sulfate, and concentrated in vacuo

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 100848-70-2, 2-Methoxy-4-methylpyridine.

Reference:
Patent; Dr. August Wolff GmbH & Co. KG Arzneimittel; GERTSCH, Juerg; EP2435019; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13296-04-3 ,Some common heterocyclic compound, 13296-04-3, molecular formula is C11H10N2, 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 159; A mixture of EXAMPLE 153 (69.2 rag), 4~pyridin-4-ylphenylamine (37.8 mg), palladium (II) acetate (3.0 mg), 4s5-bis(diphenylphosphiiio)-9,9-dirnethylxanthene (9.6 mg), cesium carbonate (141.6 mg) and dioxane (2.5 ml) were heated in a microwave at 16O0C for 40 minutes. The solvent was removed and the residue purified by flash chromatography using 20: 1 dichloromethane/methanol. Further purification by reverse phase HPLC afforded the title compound (12.8 mg, 13%). 1H NMR (DMSOd6) delta 10.40 (s, IH), 9.84 (s, IH), 8.81 (d, J=6.8 Hz, 2H), 8.38 (d, J=5.8 Hz, IH), 8.24 (d, J=6.8 Hz, 2H), 7.94-8,04 (m, 5H), 734 (d, J=5.8 Hz, IH)1 1..55-1 .75 (m, 6H), 1.27-1.36 (m, 2H), 1.17 (d, J=6.8 Hz, 3H), 0.87-1.12 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13296-04-3, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/140233; (2007); 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.3678-63-5, name is 4-Chloro-2-picoline, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.name: 4-Chloro-2-picoline

Manufacturing Example 51-1-1 (4-Chloro-pyridin-2-yl)-methanol; To a mixture of 4-chloro-2-picoline (1.0 g, 7.84 mmol) and dichloromethane (20 mL), was added m-chloroperbenzoic acid (3.5 g, 13.2 mmol) on an ice bath, which was stirred for 1.5 hours at room temperature. Water and sodium hydrogencarbonate were added to the reaction, followed by extraction with dichloromethane. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. Acetic anhydride (20 mL) was added to the residue obtained by concentrating the filtrate under a reduced pressure, and this was stirred for 1 hour at 100 C. The reaction mixture was cooled to room temperature and concentrated under a reduced pressure. A 5 N aqueous sodium hydroxide solution (1.57 mL, 7.87 mmol) was added to a mixture of the resulting residue and methanol (20 mL) on an ice bath, which was stirred for 1.5 hours at room temperature. Water was added to the mixture, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=6:1) to obtain the title compound (200 mg, 18%).1H-NMR Spectrum (CDCl3) delta (ppm): 4.76 (2H, s), 7.23-7.25 (1H, m), 7.32-7.33 (1H, m), 8.46 (1H, d, J=5.6 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3678-63-5, 4-Chloro-2-picoline, and friends who are interested can also refer to it.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, 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, Application In Synthesis of Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate

To a stirring solution of methyl 1 H-pyrazolo[3,4-c]pyridine-5-carboxylate (0.628 g, 3.545 mmol) in DMF (15 mL) was added 4-fluorobenzyl bromide (0.442 mL, 3.545 mmol) followed by potassium carbonate (0.490 g, 3.545 mmol), and the mixture was stirred overnight at room temperature. Saturated sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The crude solid was purified by flash column chromatography (silica gel, 0-20% acetonitrile: chloroform v/v) to provide pure desired methyl 1-(4-fluorobenzyl)-iH-pyrazolo[3,4-c]pyridine-5-carboxylate (0.66 g, 30% yield over three steps) and the undesired methyl 2-(4-fluoro-benzyl)-2H-pyrazolo[3,4-c]pyridine-5- carboxylate (0.73 g, 33% yield) as white solids. Methyl 1-(4-fluorobenzyl)-lH-pyrazolo[3,4- c] pyridine-5-carboxylate: (at)HNMR (CDCI3, 300 MHz) 8 ppm 8.91 (s, 1 H), 8.59 (s, 1 H), 8.22 (s, 1 H), 7.26 (m, 2H), 7.02 (m, 2H), 5.69 (s, 2H), 4.03 (s, 3H). LCMS (API-ES M+H+) 286. Methyl 2-(4- fluoro-benzyl)-2H-pyrazolo [3,4-c]pyridine-5-carboxylate: ‘HNMR (CDCI3, 300 MHz): 8 ppm 9.32 (s, 1 H), 8.51 (s, 1 H), 8.10 (s, 1 H), 7.36 (m, 2H), 7.09 (m, 2H), 5.65 (2H, s), 4.02 (s, 3H). LCMS (API-ES M+H+) 286.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; WO2005/103003; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1003711-43-0, 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.1003711-43-0, name is 2-Bromo-5-hydroxy-3-methylpyridine, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

(A) To an ice-cooled solution of 6-bromo-5-methylpyridin-3-ol (500 mg, 2.66 mmol) in DMF (10 mL) was added NaH (60% wt; 160 mg, 4.0 mmol) in a portionwise fashion and the resultant mixture was allowed to stir at rt for 1h. The mixture was then cooled to 0 C and CH3I (755 mg, 5.32 mmol) was added in dropwise fashion. After stirring for 1 h at rt, the reaction was quenched with water (20 mL) and the mixture was extracted with EtOAc (3 x 30 mL). The combined extracts were dried (Na2SO4), concentrated under reduced pressure and purified by silica gel chromatography (0-10% EtOAc/petroleum ether) to afford 2-bromo-5-methoxy-3- methylpyridine (400 mg, 74% yield) as a white solid. LC/MS: mass calcd. for C7H8BrNO: 202.05, found: 202.0, 204.0 [M, M+2]+.

The chemical industry reduces the impact on the environment during synthesis 1003711-43-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; KUO, Gee-Hong; PLAYER, Mark R.; YANG, Shyh-Ming; ZHANG, Yue-Mie; HUANG, Hui; (260 pag.)WO2016/57731; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 845306-04-9, Adding some certain compound to certain chemical reactions, such as: 845306-04-9, name is 6-Chloro-N-methylpicolinamide,molecular formula is C7H7ClN2O, 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 845306-04-9.

In a pressure tube, argon was bubbled through a suspension of 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indolin-2-one (50 mg, 197 muiotaetaomicron, Eq: 1, WO2014/202493 Al), 6-chloro- N-methylpicolinamide (40.4 mg, 237 muiotaetaomicron, Eq: 1.2) and cesium carbonate (83.6 mg, 257 muiotaetaomicron, Eq: 1.3) in dioxane (987 mu) for 5 minutes. Xantphos (22.8 mg, 39.5 muiotaetaomicron, Eq: 0.2) and tris(dibenzylideneacetone)dipalladium (0) (36.2 mg, 39.5 muiotaetaomicron, Eq: 0.2) were added and the reaction mixture was heated to 120 C for 1 day under argon. The residue was evaporated in vacuo and purified by chromatography on silica gel, followed by prep HPLC to afford the desired product as a light yellow solid (45 mg, 58 ). MS (m/z) = 388.2 [M + H]+.

According to the analysis of related databases, 845306-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GAUFRETEAU, Delphine; KOLCZEWSKI, Sabine; PLANCHER, Jean-Marc; STOLL, Theodor; HALM, Remy; (85 pag.)WO2017/76852; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14916-65-5, 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. 14916-65-5, name is 6-Nitropyridin-3-amine, molecular formula is C5H5N3O2, 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 V-1 was synthesized through the reaction of 5-amino-2-nitropyridine with sodium azide and orthoformate and subsequent reduction with hydrogen in the presence of palladium hydroxide/activated carbon

According to the analysis of related databases, 14916-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teijin Pharma Limited; MIZUNO, Tsuyoshi; SHIMADA, Tomohiro; UNOKI, Gen; EBISAWA, Masaru; TAKEUCHI, Susumu; MINAMIZONO, Kunio; SASAKI, Kosuke; YOKOSAKA, Takuya; IGARASHI, Junji; MARUYAMA, Akinobu; TAKAHASHI, Hiroshi; HORIE, Kyohei; SAKAI, Yuri; (447 pag.)EP3305785; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2546-56-7 ,Some common heterocyclic compound, 2546-56-7, molecular formula is C5H3ClFN, 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.

[00408] Intermediate 101 A. 2-Bromo-4-chloro-3-fluoropyridine: To a solution of 2,2,6, 6-tetramethylpiperidine (1.54 mL, 9.12 mmol) in THF (40 mL) was added 1.6 Mu kappa- BuLi in hexanes (5.23 mL, 8.36 mmol) dropwise at -78 C. The resulting solution was stirred for 0.5 h at 0 C. It was then cooled to -78 C and 4-chloro-3-fluoropyridine (0.769 mL, 7.60 mmol) in 5 mL THF was added dropwise over 30 min. The resulting solution was stirred at -78 C for 30 min. To the solution was added NBS (1.624 g, 9.12 mmol) in THF (25 mL) dropwise and the resulting solution was stirred for 1 h at -78 C, then at ambient temperature for 12 h. The reaction mixture was then diluted with EtOAc and water. The organic layer was washed with brine, concentrated and purified on silica gel chromatography to give the desired product (0.541 g, 34%) as orange oil (volatile). 1H NMR (400 MHz, CDC13) delta 8.13 (d, J = 5.0 Hz, 1H), 7.35 (t, J = 5.1 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2546-56-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem