Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 102074-19-1, (5-Methylpyridin-3-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, Computed Properties of C7H9NO, blongs to pyridine-derivatives compound. Computed Properties of C7H9NO

Step 2. 5-methyl-3-pyridinecarboxaldehyde. A mixture of 5-methyl-3-pyridinemethanol (106 mg, 0.86 mmol) and activated MnO2 (376 mg) in methylenechloride (10 mL) was stirred at room temperature overnight. The black solid of MnO2 was removed by filtration. The filtrate was concentrated in vacuo to yield the title compound as an oil (100 mg, 85%). 1H NMR (CDCl3): 10.10 (s, 1H), 8.89 (s, 1H), 8.68 (s, 1H), 7.98 (s, 1H), 2.45 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,102074-19-1, (5-Methylpyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Cytovia, Inc.; EP1230232; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89510-90-7, 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. 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine. A new synthetic method of this compound is introduced below.

A microwave vial charged with 2-Chloro-5-fluoropyridin-4-amine (500 mg, 3.41 mmol) and (S)-3-Methylmorpholine (3102 pi, 27.3 mmol) was heated in the microwave at 210 C for 52 hours. The crude product was concentrated onto celite and purified on the Biotage (reverse phase silica gel) eluting with 0-50% ACN/H2O. The desired fractions were collected, concentrated and dried under high vacuum at RT to afford (S)-5-fluoro-2-(3- methylmorpholino)pyridin-4-amine (2.94 mmol, 86 % yield) as a sticky brown solid. 1 H NMR (500MHz, DMSO-d6) d = 7.70 (d, J=3.1 Hz, 1 H), 5.96 (d, J=6.4 Hz, 1 H), 5.85 (s, 2H), 4.1 1 – 4.05 (m, 1 H), 3.87 (dd, J= 3.5, 1 1 .1 Hz, 1 H), 3.68 – 3.64 (m, 1 H), 3.61 – 3.56 (m, 1 H), 3.51 (dd, J=2.1 , 12.8 Hz, 1 H), 3.43 (dt, J=3.1 , 1 1 .6 Hz, 1 H), 2.92 (dt, J= 3.7, 12.4 Hz, 1 H), 1 .02 (d, J= 6.6 Hz, 3H); LCMS (m/z): 212.4 [M+1 ]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ISAAC, Methvin; CHAU, Anh My; MAMAI, Ahmed; WATSON, Iain; PODA, Gennady; SUBRAMANIAN, Pandiaraju; WILSON, Brian; UEHLING, David; PRAKESCH, Michael; JOSEPH, Babu; MORIN, Justin-Alexander; (441 pag.)WO2019/153080; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 120739-77-7 ,Some common heterocyclic compound, 120739-77-7, molecular formula is C8H11ClN2, 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.

In a 100 mL three neck round bottom flask, 17.0 g (0.1 mol) of N-(6-chloropyridine-3-methylene)ethylamine, 15.0 g (0.09 mol) of 1,1-dimethylthio-2-nitroethylene, and 50 mL of absolute ethanol were added. Heated to reflux. Reflux for 8h. Stop reflow, cooled to room temperature. Concentrated to viscous liquid. Silica gel column chromatography (dichloromethane: acetone = 5: 1 (v / v)) gave the product 6.5 g (compound IV-1) in a yield of 23%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,120739-77-7, its application will become more common.

Reference:
Patent; East China University of Science and Technology; Li, Zhong; Xu, Xiaoyong; Yuan, Zihao; Lu, Siyuan; Shao, Xusheng; Xu, Zhiping; (66 pag.)CN105669660; (2016); A;,
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.96428-50-1, name is Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, molecular formula is C18H18N2O3, molecular weight is 310.35, as common compound, the synthetic route is as follows.SDS of cas: 96428-50-1

253 ml of 2 N aqueous sodium hydroxide solution were added to a solution of 15.7 g of ethyl 8-(benzyloxy)- 2-methylimidazo[1 ,2-a]pyridine-3-carboxylate (50.59 mmol) from Example 38A in 253 ml of 1 ,4-dioxane, and the mixture was stirred at RT for 14 h. 101 ml of 6 N aqueous hydrochloric acid were then added. The solid formed was filtered off, washed with water and methyl tert-butyl ether and then dried under reduced pressure at 40 C. overnight. This gave 15.49 g (108% of theory) of 8-(benzyloxy)-2- methylimidazo[1 ,2-a]pyridine-3-carboxylic acid.10698] LC-MS (Method 2): R=0.66 mm10699] MS (ESpos): mlz=283.0 (M+H)10700] ?H-NMR (400 MHz, DMSO-d5): oe=2.67 (s, 3H),5.41 (s, 2H), 7.30 (m, 1H), 7.35-7.48 (m, 4H), 7.57 (d, 2H),9.02 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96428-50-1, Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; GROMOV, Alexey; FOLLMANN, Markus; BROCKSCHNIEDER, Damian; STASCH, Johannes-Peter; MARQUARDT, Tobias; TERSTEEGEN, Adrian; WUNDER, Frank; REDLICH, Gorden; LANG, Dieter; LI, Volkhart Min-Jian; (95 pag.)US2016/347770; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131747-62-1, 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 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Sodium triacetoxyborohydride (40 mg, 0.19 mmol) was added to a solution of (3-((1- amino-2,3-dihydro-1 H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol (30 mg, 0.093) and 3-trifluoromethyl-2-formylpyridine (15 mg, 0.086 mmol) in DCM (1 ml_). The reaction was stirred at rt for 24 h before aq. sat. NaHCO3 (2 ml.) was added to the mixture was filtered over a phase separator. The organic filtrate was evaporated to dryness in a Genevac. The crude material was purified by prep. LCMS to afford the title compound (18.9 mg, 42.1 %). MS (ESI) : m/z [M + H]+ 481.2

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 131747-62-1, 3-(Trifluoromethyl)pyridine-2-carboxaldehyde.

Reference:
Patent; N.V. Organon; GILLEN, Kevin James; GILLESPIE, Jonathan; JAMIESON, Craig; MACLEAN, John Kinnaird Ferguson; MOIR, Elizabeth Margaret; RANKOVIC, Zoran; WO2010/115952; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55404-31-4, Adding some certain compound to certain chemical reactions, such as: 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine,molecular formula is C6H5BrClN, 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 55404-31-4.

(2) Synthesis of 3-bromo-2-methoxy-4-methylpyridine 3-bromo-2-chloro-4-methylpyridine (1 g) was added to DMF (5.6 mL). Sodium methoxide (28% solution in methanol, 4.6 mL) was added to the solution, and the mixture was stirred at 100 C. for 12 hours. The reaction mixture was partitioned by adding ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (1.1 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.40 (s, 3H), 4.00 (s, 3H), 6.77 (d, J=5.1 Hz, 1H), 7.94 (d, Hz, 1H).

According to the analysis of related databases, 55404-31-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 408365-87-7, 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.408365-87-7, name is Ethyl 2-(6-((tert-butoxycarbonyl)amino)pyridin-2-yl)acetate, molecular formula is C14H20N2O4, molecular weight is 280.32, as common compound, the synthetic route is as follows.

2C. (6-amino-pyridin-2-yl) acetic acid ethyl ester; To a solution of title compound 2B, (6-te;’t-butoxycarbonylamino-pyridin-2-yl) acetic acid ethyl ester, (1.38 g, 4.92 mmol) in DCM (20 ml) is added 4M HCl in dioxane (4 eq, 19.7 mmol) and the mixture is stirred for 4 h at room temperature. A further 4 eq of 4M HCl in dioxane are added and the mixture is left to stir for 16 h. The reaction mixture is concentrated in vacuo to give the title compound (1.20 g, > 100% ~14% starting material remained). LC/MS: 75% MH+, m/z 181, Rt = 0.68 mins. The product is used crude without further purification.

The chemical industry reduces the impact on the environment during synthesis 408365-87-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; EVOTEC AG; WO2006/50908; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 623585-74-0, Adding some certain compound to certain chemical reactions, such as: 623585-74-0, name is Methyl 2,5-dichloroisonicotinate,molecular formula is C7H5Cl2NO2, 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 623585-74-0.

A mixture of 5-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyrimidine (3 g, 10.95 mmol, 1.00 equiv), methyl 2,5-dichloropyridine-4-carboxylate (6 g, 29.12 mmol, 1.00 equiv), Pd(dppf)C12 (1.55 g, 2.12 mmol, 0.20 equiv), and potassium carbonate (8.78 g, 63.53 mmol, 5.80 equiv) in dioxane (100 mL)/water(5 mL) was stirred for 12 h at 60C under nitrogen. The reaction mixture was concentrated under vacuum. The residue purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:10) to afford the title compound (1.4 g, 40%) as a white solid.

According to the analysis of related databases, 623585-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); 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.823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, molecular weight is 260.44, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine

To a solution of 5-bromo-2-chloro-4-trifluoromethyl-pyridine (1.0 g, 3.84 mmol) in EtOH (5 mL) was added freshly prepared 1M solution of sodium ethanolate in EtOH (5.76 mL, 5.76 mmol) at RT and the resulting RM was heated to reflux for 2 h. The RM was concentrated under reduced pressure and subsequently diluted with CH2Cl2, washed with water and brine and dried. The solvent was evaporated under reduced pressure to yield the desired compound (700 mg, 67%) which was used in next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, FELIX; NORDHOFF, SONJA; WACHTEN, SEBASTIAN; WELBERS, ANDRE; RITTER, STEFANIE; US2015/166505; (2015); 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. 124236-37-9, name is Methyl 5-(trifluoromethyl)picolinate, molecular formula is C8H6F3NO2, 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. Recommanded Product: Methyl 5-(trifluoromethyl)picolinate

Step 2: (0564) To a mixture of methyl 5-(trifluoromethyl)pyridine-2-carboyxlate prepared above (0.2 g, 0.97 mmol) and (trifluoromethyl)trimethylsilane (0.173 g, 1.22 mmol) stirring at -78 C. in pentante (3 mL) under a nitrogen atmosphere was slowly added tetrabutylammonium fluoride (1.0 M in THF, 25 muL, 0.024 mmol). The reaction was allowed to come to room temperature and stirred overnight (total reaction time 16 hours). At that time, 2 N HCl was added, and the mixture was stirred vigorously at room temperature for 2 hours. The solution was extracted with DCM. The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-20% EtOAc/hexanes over 20 minutes) to provide the trifluoromethyl ketone product (0.084 g, 35%).

With the rapid development of chemical substances, we look forward to future research findings about 124236-37-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; Scott, Jack D.; Stamford, Andrew W.; Gilbert, Eric J.; Cumming, Jared N.; Iserloh, Ulrich; Misiaszek, Jeffrey A.; Li, Guoqing; US2015/307465; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem