Month: April 2022

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

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

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

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

Electric Literature of 1231930-13-4 , The common heterocyclic compound, 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine, molecular formula is C6H5BrN2O2, 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.

A mixture of Example C7 (1.185 g, 3.93 mmol), Example A6 (0.746 g, 2.81 mmol), K2CO3 (1.165 g, 8.43 mmol) and Pd(PPh3)4 (0.325 g, 0.281 mmol) in dioxane (11 mL) and water (3 mL) was sparged with Ar and heated at 90 C. overnight. The mixture was cooled to RT, treated with EtOAc and brine and the solids removed via filtration through diatomaceous earth. The layers of the filtrate were separated, the aqueous layer extracted with additional EtOAc (3*) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 2-methyl-3-((2-(4-(1-methylpiperidin-4-yl)phenyl)pyridin-4-yl)oxy)-6-nitropyridine (553 mg, 49%). MS (ESI) m/z: 405.2 (M+H+).

The synthetic route of 1231930-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); 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

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.851607-27-7, name is 5-Bromo-4-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-4-chloro-2-methoxypyridine

To a solution of cyclopropylmethanol (446 mg, 6.18 mmol) in THF (10 mL) was added NaH (247 mg, 6.18 mmol, 60% in mineral oil) in one portion at 0 C. The reaction mixture was warmed up to 20 C. over a period of 30 mins and stirred at 20 C. for 10 mins. Then 5-bromo-4-chloro-2-methoxypyridine (550 mg, 2.47 mmol) was added in one portion and the mixture was stirred at 70 C. for 4 hours. The mixture was diluted with saturated ammonium aqueous solution (50 mL) and extracted by EtOAc (2*30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude product which was purified by silica gel column chromatography (PE:EA=20:1 to 10:1) to afford the title compound (450 mg, 70.6%) as colorless oil. 1H NMR: (CDCl3, 400 MHz) delta: 8.11 (s, 1H), 6.18 (s, 1H), 3.90 (s, 3H), 3.89-3.88 (m, 2H), 1.39-1.27 (m, 1H), 0.70-0.67 (m, 2H), 0.46-0.43 (m, 2H). LCMS (M+H)+=258.0 (M+1)+; 260.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound,851607-27-7, 5-Bromo-4-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kaldor, Stephen W.; Stafford, Jeffrey Alan; Veal, James Marvin; US2015/111885; (2015); A1;,
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

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. 929617-30-1, name is 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine. A new synthetic method of this compound is introduced below., Product Details of 929617-30-1

Into a 30 mL sealed tube was placed 5-bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine (900 mg, 4.24 mmol), Pd(dppf)CI2 (315 mg, 0.43 mmol), KOAc (1.25 g, 12.7 mmol) and N,N- dimethylformamide (10 mL). This was followed by the addition of methanol (10 mL) and CO gas. The solution was stirred for 1 h overnight at 80C in an oil bath. The mixture was concentrated under vacuum. The residue was purified over a silica gel column with dichloromethane/methanol (20:1). This resulted in 0.60 g (74%) of methyl 3-methyl-1H- pyrazolo[3,4-c]pyridine-5-carboxylate as a brown solid.

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, 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LTD.; SCHIEMANN, Kai; MALLINGER, Aurelie; (147 pag.)WO2016/26549; (2016); 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