Tag: M.W:200-300

Application of 878197-68-3 ,Some common heterocyclic compound, 878197-68-3, molecular formula is C8H5BrN2O, 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.

Alternatively 5-(4-Methyl-1-piperazinyl)imidazo[1 ,2-a]pyridine-2-carbaldehyde can be prepared as follows: EPO A reactor is charged with 2-amino-6-bromopyridine (3.0 Kg1 17.3 mol) and dimethoxyethane ( 12 Liters) and stirred under nitrogen. 1 ,1 ,3-Trichloroacetone (5.6 Kg, 30.3 mol) is added to the 25 C solution in a single portion and the reaction solution is warmed to 65 0C jacket temperature and maintained for approximately 2 to 4 hours until judged complete. The reaction is cooled to 10 C and held for approximately one hour and filtered. The solids are rinsed with dimethoxyethane (6 Liters). The solid is placed back in the reactor and treated with dimethoxyethane (12 Liters) and 2N HCI (12 Liters) and warmed to aproximately 75 degrees for 16 to 20 hours or until judged complete. The reaction is cooled to approximately 1O0C and pH is adjusted to approximately 8 with 3 N NaOH. The resulting solids are filtered and washed with water. The solid is dried at 50 0C for 16 hours to yield 5-bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde, (2.81 Kg, 72% yield) 1 H NMR (400 MHz, DMSO-D6) delta ppm 10.05 (s, 1 H) 8.66 (s, 1 H) 7.72 (s, 1 H) 7.42 (s, 1 H) 7.35 (s, 1 H). The reactor is charged with N-methylpiperazine (3.1 Kg, 31 mol ) and tetrahydrofuran (10 Liters) and stirred under nitrogen while cooling to negative 20 0C. n- Butyl lithium (10.4 L, 26.0 mol) is added to the reaction at a rate to maintain the negative 20 0C temp and the contents are stirred for 15 to 30 minutes. A slurry of 5- bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (2.79 Kg, 12.4 mol) in tetrahydrofuran (10 Liters) is added at a rate to maintain the reaction at ?0C. The slurry is washed in with additional tetrahydrofuran (6 Liters). The reaction is stirred for 30 minutes and warmed to approximately negative 10 0C. The reaction is quenched by addition of 6N HCI solution to achieve pH 4.0 while maintaining at ? 150C. The reaction is diluted with heptane (14 Liters) and the layers allowed to separate. The lower aqueous layer is drained and the upper organic layer is washed with 1 N HCI (2 x 1.5 Liters). The combined aqueous layers are stirred at 20 degrees and adjusted to pH 9 with 4N NaOH solution. The Aqueous layer is extracted with 10% iPrOH/CH2CI2 (3 x 28 Liters) and the combined organic layers are washed with saturated NaHCO3 solution (14 Liters) and evaporated at <25 0C to approximately 3 volumes, lsopropanol (28 Liters) is added and reaction again concentrated under reduced pressure to approximately 8.5 Liters, lsopropanol (17 Liters) is added and the reaction is treated with a solution of oxalic acid (1.0 Kg, 11.1 mol) in isopropanol (7 Liters) at a rate to maintain good stirring and temperature between approximately 25-4O0C. The reaction is stirred for 30 minutes and the solids are collected and washed with isopropanol (8.5 Liters) Solids are dried at 50 0C to yield 5-(4-methyl-1- piperazinyl)imidazo[1 ,2-a]pyridine-2-carbaldehyde, (2.25 Kg, 54% yield) 1 H NMR (400 MHz, DMSO-D6) delta ppm 10.01 (s, 1 H) 8.47 (s, 1 H) 7.41 (m, 2 H) 6.65 (m, 1 H) 3.34 (s, 8 H) 2.78 (s, 3 H) These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,878197-68-3, its application will become more common. Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/76131; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75073-11-9, 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.75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, molecular weight is 234.04, as common compound, the synthetic route is as follows.

3. Take 12.20 g of compound 10 and 14.60 g of p-acetamidobenzenesulfonyl chloride (compound 4), add it to 200 mL of pyridine, and stir at room temperature for 24 h. Under vacuum, remove the organic reagents to a volume of 50 mL. 200 mL of water was added and a precipitate formed. The precipitate was filtered, washed with 200 mL of water, and dried under vacuum to obtain 9.40 g (compound 11) of a white powder with a yield of about 42%.

Statistics shows that 75073-11-9 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-6-methylpyridin-2-amine.

Reference:
Patent; China Agricultural University; Wang Zhanhui; Shen Jianzhong; Wen Kai; Li Chenglong; Yu Xuezhi; Zhang Suxia; Shi Weimin; Yu Wenbo; (19 pag.)CN110713457; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 934279-60-4, 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. 934279-60-4, name is 2-Chloro-5-(trifluoromethyl)nicotinaldehyde. A new synthetic method of this compound is introduced below.

A mixture of 2-chloro-5-trifluoromethylpyridine-3-carboxaldehyde (330 mg, 1.6 mmol), trans- (/?)-2-[4-(benzyloxyethyl)cyclohexyl]pyrrolidine (410 mg, 1.5 mmol), potassium carbonate (310 mg. 2.2 mmol) in toluene (3.5 ml_) is stirred under reflux condition for 5 hours. After cooling to room temperature, water and dichloromethane are added and the mixture is extracted with dichloromethane. The combined organic layer is filtered through phase separator and concentrated. The residue is purified by silica gel column chromatography to give frans-2-{(R)-2-[4-(2-ben2yloxyethyl)cyclohexyl]pyrrolidin-1-yl}-5-trifluoromethylpyridine-3-carboxaldehyde (527 mg).0.82-1.23 (m, 4H), 1.69-1.55 (m, 4H), 1.81-1.91 (m, 3H), 1.92-2.11 (m, 3H), 2.98-3.03 (m,1H), 3.23 (d, 2H), 3.65-3.72 (m, 1H), 4.48 (s, 2H), 4.52-4.70 (m, 1H), 7.32 (s, 1H), 7.25-7.37(m, 5H), 8.11 (d, 1H), 8.50 (d, 1H), 9.93 (s. 1H).Rf value: 0.41 (Hexane/EtOAc = 9/1 )

At the same time, in my other blogs, there are other synthetic methods of this type of compound,934279-60-4, 2-Chloro-5-(trifluoromethyl)nicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/73934; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6945-67-1, Adding some certain compound to certain chemical reactions, such as: 6945-67-1, name is 2-Bromo-4-nitropyridine,molecular formula is C5H3BrN2O2, 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 6945-67-1.

The 2-bromo-4-nitropyridine (200mg, 0.99mmol),4-hydroxypiperidine (149.48mg, 1.48mmol) and cesium carbonate(642.02mg, 1.97mmol) placed in the reaction flask, add 20mL 1,4-Dioxane, react overnight at 100C. The reaction is over,Cool to room temperature, filter,The filtrate was concentrated and purified by column chromatography to obtain the title compound.

According to the analysis of related databases, 6945-67-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Wang Yazhou; Quan Xu; Liu Haixuan; Wang Xiaowei; Zhang Yan; Li Xue; Cao Chen; Guo Zhuang; Lv Kunzhi; Wang Hai; Zheng Guochuang; (126 pag.)CN111196804; (2020); A;,
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. 381247-99-0, name is Methyl 5-bromo-6-hydroxynicotinate. A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 5-bromo-6-hydroxynicotinate

Methyl 3-(5-(2-(((4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyl-2-oxooxazolidin-3-yl)methyl)-4,4-dimethylcyclohex-1-enyl)-6-methoxypyridin-3-yl)-2,2-dimethylpropanoate [0562] As shown in reaction scheme 7, Compound 31, an intermediate compound, was synthesized, and then Compound 349 (0.28 g, 69.5%) as white solid foam was obtained according to the similar method to the synthesis of compound 285. [0563] 1H NMR (400 MHz, DMSO-d6); atropisomer mixture; delta7.86 (m, 1H), 7.81, 7.83 (2d, 1H, J=1.77, 1.83 Hz), 7.74-7.75 (m, 2H), 7.02, 7.05 (2d, 1H, J=1.77, 1.77 Hz), 5.60, 5.63 (2d, 1H, J=5.94, 6.00 Hz), 3.91-4.03 (m, 2H), 3.85, 3.88 (2d, 3H), 3.64, 3.65 (2s, 3H), 3.46-3.52 (m, 1H), 2.73-2.80 (m, 2H), 1.90-1.95 (m, 2H), 1.43-1.48 (m, 2H), 1.16-1.20 (m, 6H), 1.01-1.09 (m, 6H), 0.28, 0.49 (2d, 3H, J=4.89, 4.89 Hz); MS (ESI) m/z 657.2 (M++H)

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, 381247-99-0, Methyl 5-bromo-6-hydroxynicotinate.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; Lee, SeoHee; Oh, Jung Taek; Lee, JaeKwang; Lee, JaeWon; Bae, Suyeal; Ha, Nina; Lee, Sera; US2014/31335; (2014); A1;,
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. 1352625-30-9, name is 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine, the common compound, a new synthetic route is introduced below. name: 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine

c) 6-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine A mixture of 3-bromo-6-fluoropyrazolo[1,5-a]pyridine (Preparation 103b, 0.300 g, 1.4 mmol), potassium acetate (0.492 g, 5.0 mmol) and bis(pinacolato)diboron (2.77 g, 10.9 mmol) in 1,4-dioxane (5 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and tetrakis(triphenylphosphine)palladium(0) (0.380 g, 0.33 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was purified by reverse phase chromatography (C-18 silica from Waters, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (0.130 g, 36%) as a yellow solid. LRMS (m/z): 263 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm (two sets of peaks are seen in the NMR due to the presence of both the boronate and boronic acid): NMR of boronate: 1.21 (s, 12H), 7.56 (m, 1H), 8.02 (m, 1H), 8.36 (s, 1H), 9.16 (m, 1H).

The synthetic route of 1352625-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 69045-78-9 ,Some common heterocyclic compound, 69045-78-9, molecular formula is C6H3Cl4N, 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.

The recovered organic materials include the object products as well as 20% of 2-chloro-5-fluorodichloromethylpyridine and 6.7% of 2-chloro-5-chlorodifluoromethylpyridine as intermediates and 3.8% of the unreacted 2-chloro-5-trichloromethylpyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-78-9, its application will become more common.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4266064; (1981); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 185041-05-8 ,Some common heterocyclic compound, 185041-05-8, molecular formula is C7H5ClINO2, 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.

[00324] To a solution of compound 13 (5.5 g, 18.5 mmol) in DMF (50 mL) was added K2C03 (10.2 g, 74 mmol), trimethylboroxine (4.64 g, 3.70 mmol) and Pd(PPh3)4 (2.1 g, 1.85 mmol) in DMF under N2. The reaction mixture was stirred at 110 C for 120 mm under N2. After cooled down, water (100 mL) was added into the mixture. Et20 was added to extract the product, washed by water and dried over Na2SO4 .Concentrated and purified by FCC (PE/EA=40: 1) to afford 2.7 g of the product 14 (79%).

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. 185041-05-8, Methyl 2-chloro-4-iodonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; YANG, Wenjin; CHEN, Che-Hong; MOCHLY-ROSEN, Daria; WO2014/160185; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67625-38-1, Ethyl 6-chloroimidazo[1,2-a]pyridine-2-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, name: Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate, blongs to pyridine-derivatives compound. name: Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate

A solution of ethyl 6-chloroimidazo[l,2-a]pyridine-2-carboxylate (0.8 g, 3.6 mmol), cesium carbonate (1.3 g, 3.9 mmol), palladium acetate (64 mg, 0.29 mmol), andtriphenylphosphine (0.15 g, 0.57 mmol) in 1,4-dioxane (43 mL) was treated with l-bromo-3- fluorobenzene (0.54 mL, 4.8 mmol), degassed with nitrogen, and heated in the microwave at 150 C for 30 min. The reaction mixture was filtered over celite and the filtrate was concentrated to give a crude residue. This material was purified by flash column chromatography to give the desired product (1.2 g, 94%). LCMS for C16H13C1FN202 (M+H)+: m/z = 319.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67625-38-1, Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew P.; LI, Yun-Long; YUE, Eddy W.; SPARKS, Richard B.; WO2011/75643; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54232-43-8, 6-Bromo-5-methoxypicolinic acid, 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, 54232-43-8, blongs to pyridine-derivatives compound. Computed Properties of C7H6BrNO3

4,87g (21 mmol) 6-Bromo-5-methoxy-pyridine-2-carboxylic acid and 4, 17g (25,2 mmol, 1 ,2eq) CDI are suspended in 54ml Me-THF and heated to 50C. After stirring for 3,5h at this temperature the mixture is cooled to 0C in an ice bath and 3,39ml (24,2, 1 , 15eq) triethyl-amine is added. After that 6, 1 g (23, 1 mmol, 1 , 1 eq)of (S)-3- Amino-3-(2-chloro-phenyl)-propionic acid ethyl ester are added within 20 minutes and the resulting mixture is allowed to reach RT and stirred overnight.50 ml water is added, the phases are separated and the organic phase is washed several times with 50ml of saturated NaHC03 solution followed by 50ml of 1 N HCI solution. The organic phase is evaporated in vacuo and 8,43g of product are obtained. Yield: 89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54232-43-8, its application will become more common.

Reference:
Patent; SANOFI; RUF, Sven; SADOWSKI, Thorsten; WIRTH, Klaus; SCHREUDER, Herman; BUNING, Christian; WO2012/101197; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem