Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 143150-92-9, 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, 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, Safety of 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, blongs to pyridine-derivatives compound. Safety of 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

[Referential Example 13] Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine-2-carboxylate: 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine (531 mg) was dissolved in absolute diethyl ether (20 ml), n-butyllithium (1.54N hexane solution, 1.63 ml) was added dropwise at -78C, and the mixture was stirred for 30 minutes with ice cooling. After passing carbon dioxide into the reaction mixture at -78C for 1 hour, the mixture was warmed to room temperature. The reaction mixture was concentrated under reduced pressure to obtain the title compound (523 mg) as a pale brown solid. 1H-NMR (DMSO-d6) delta: 2.37(3H,s), 2.64-2.77(4H,m), 3.54(2H,s) MS (FAB) m/z: 199(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,143150-92-9, 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1270557; (2003); 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. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below., name: 3-Iodo-1H-pyrazolo[3,4-b]pyridine

Add 400 g (1.63 mol, 1.0 eq) of 3-iodo-1H-pyrazolo[3,4-b]pyridine, 369 g (1.96 mol, 1.2 eq) of o-fluorobenzyl bromide and 450 g (3.27 mol, 1.5 eq) of K2CO3 dissolved in 4L of DMF into a 5L 4-neck flask and react for 10 h at room temperature. Pour the reaction solution into water after thorough reaction as monitored by TLC, stir it to appear a plenty of grey solid, filter and recrystallize PE: EA=5:1 to obtain 411 g of light yellow solid. The yield is 71.16%. [0025] 11 H NMR (400 MHz, CDCl3) delta (ppm): 8.62 (d, 1H), 7.85 (d, 1H), 7.27 (dd, 1H), 7.11 (dd, 1H); 6.96-7.08 m, 3H), 5.82 (s, 2H).

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, 117007-52-0, 3-Iodo-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; Pharmablock (Nanjing) R&D Co., Ltd.; Li, Jin; Yang, Xiaoyu; Zhu, Jingwei; Yang, Minmin; Wu, Xihan; US2014/309425; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 39856-50-3, 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.39856-50-3, name is 5-Bromo-2-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

To a solution of compound (1) (20.00 g, 98.53 mmol, 1.00 eq) in dimethyl sulfoxide (52 mL), compound (2) (24.00 g, 128.86 mmol, 1.31 eq) and triethylamine (20.00 g, 197.65 mmol, 2.01 eq) were added. The solution was heated to 60 C. and stirred for 18 hours. TLC (petroleum ether:ethyl acetate=3:1) showed the completion of the reaction. The solution was diluted with water (200 mL), stirred for 30 minutes, and then filtered. The filter cake was washed with water and dried under vacuum to obtain a crude product. The crude product was purified by a silica gel column (petroleum ether:ethyl acetate=50:1 to 20:1) to obtain compound (3) (27.00 g, 87.57 mmol, yield: 88.87%). 1H NMR (400 MHz, CDCl3) delta8.18 (d, J=9.03 Hz, 1H), 8.13 (d, J=2.89 Hz, 1H), 7.21 (dd, J=9.10, 2.95 Hz, 1H), 3.69-3.59 (m, 4H), 3.51-3.40 (m, 4H), 1.49 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 39856-50-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Ding, Charles Z.; Chen, Shuhui; Hu, Lihong; Xu, Zhaobing; Liu, Yingchun; Ren, Bingjie; Li, Weidong; Li, Zongbin; Zhao, Rui; Zhang, Xiquan; (21 pag.)US2019/194168; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 799293-85-9, Adding some certain compound to certain chemical reactions, such as: 799293-85-9, name is 3-Bromothieno[3,2-c]pyridin-4-amine,molecular formula is C7H5BrN2S, 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 799293-85-9.

EXAMPLE 10A 3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine A mixture of Example 1B (1.5 g, 6.5 mmol), 4-phenoxyphenylboronic acid (1.53 g, 7.1 mmol) and Na2CO3 (1.81 g, 17.1 mmol) in toluene (26 mL), ethanol (5 mL), and water (10 mL) was purged with nitrogen for 45 minutes, then treated with Pd(PPh3)4 (0.382 g, 0.33 mmol) and heated to 90 C. overnight. The reaction was cooled to room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate twice and the combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 40% ethyl acetate/hexanes to provide 1.69 g (82% yield) of the desired product. MS (ESI(+)) m/e 318.9 (M+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. 799293-85-9, 3-Bromothieno[3,2-c]pyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.; US2005/43347; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5349-17-7, 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.5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, molecular formula is C7H7Br2NO, molecular weight is 280.9446, as common compound, the synthetic route is as follows.

To a solution of 2-Bromo-l-(4-pyridinyl)-l-ethanone hydrobromide (4.0 g, 14.4 mmol) in anhydrous ethanol (80 ml) is added NaBH4 (2.0 g, 52.8 mmol). The reaction mixture is stirred at RT for 2 h. The mixture is filtered and l-(2-Phenylethyl)piperazine (4.9 ml, 26.0 mmol) is added to the filtrate. The solution is heated to reflux and refiuxed for 5 h. Excessive ethanol is removed by distillation. The resulting pale yellow solid is dissolved in chloroform (80 ml), the insoluble parts are filtered off and the filtrate is concentrated by distillation under reduced pressure. The product is purified by chromatography on silica (MeOH/EtOAc, 5:1) to give a pale yellow solid; yield: 32 % ; chemical formula: Ci9H2SN3O; molecular weight: 311,42.1H NMR (300 MHz, CDCl3) delta 2.83 – 2.84 (m, 14H), 4.73 (dd, IH, J= 10.5 Hz, J = 3.8 Hz),7.20 – 7.30 (m, 5H), 7.31 (dd, 2H, J = 4.7 Hz, J = 1.5 Hz), 8.57 (dd, 2H, J = 4.4 Hz, J = 1.5Hz);FT-IR (KBr) 3420, 1639, 1458, 1409, 1128, 854, 696, 622 cm”1;EI MS mZz SlO [M-H+];HR MS m/z calcd for C19H24N3O [M-H+] C9H24N3O 310.191938, found 310.192050.

Statistics shows that 5349-17-7 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2007/73935; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 15862-37-0, name is 2,5-Dibromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H2Br2N2O2

5-Bromo-2-(3-methoxyphenyl)-3-nitropyridine A stirred mixture of 2,5-dibromo-3-nitropyridine (0.2621 g, 0.930 mmol), 3-methoxyphenylboronic acid (0.155 g, 1.02 mmol), tetrakis(triphenylphosphine)-palladium (0.076 g, 0.065 mmol), and 2.0M sodium carbonate (2.4 mL, 4.80 mmol) in toluene (3.0 mL) and ethanol (1.0 mL) was heated to 70 C. After 2.5 h, the reaction was cooled to rt then diluted with water. After extraction with EtOAc, the organic extraction was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified on silica gel (0-20% EtOAc in hexanes) to afford a yellow solid as 5-bromo-2-(3-methoxyphenyl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) delta ppm 8.91 (1H, d, J=2.2 Hz), 8.27 (1H, d, J=2.2 Hz), 7.42 (1H, m), 7.14 (3H, m), 3.86 (3H, s).

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, 15862-37-0, 2,5-Dibromo-3-nitropyridine.

Reference:
Patent; AMGEN INC.; US2010/331293; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 71701-92-3, 3-Bromo-2-chloro-5-(trifluoromethyl)pyridine, 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, 71701-92-3, blongs to pyridine-derivatives compound. Safety of 3-Bromo-2-chloro-5-(trifluoromethyl)pyridine

A mixture of 3-bromo-2-chloro-5-(trifluoromethyl)pyridine (260 mg), trimethylsilyl acetylene (98.2 mg), tetrakis-triphenylphosphine palladium (0) (23.1 mg), copper iodide (3.8 mg), triethylamine (4 ml) and benzene (1 ml) was heated to 60 C. After the reaction mixture was stirred all night and all day, it was kept standing to cool to room temperature, and the, the solvent was distilled off in vacuo. To the residue was added ethyl acetate, and the organic layer was separated. The organic layer was washed with a saturated saline, and dried with anhydrous sodium sulfate. Then, the organic layer was filtrated and concentrated, and the residue was purified by the silica gel column chromatography affording the compound 2 (226 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71701-92-3, its application will become more common.

Reference:
Patent; Mitsubishi Tanage Pharma Corporation; US2012/258951; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 80194-68-9 ,Some common heterocyclic compound, 80194-68-9, molecular formula is C7H3ClF3NO2, 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 third step: 0.24g2-(4-(methylthio)phenoxy)acetyl hydrazine and0.25g3-Chloro-5-trifluoromethylpicolinic acid added to the tube with a thermowellIn a 50 mL three-necked flask, 4 mL of POCl3 was added, the stirrer was turned on, and the mixture was heated and stirred, followed by heating to 100 C. The progress of the reaction was followed by TCL, and when it was detected that the starting point of the reaction system disappeared, the reaction was stopped.Post-treatment: The reaction solution was slowly introduced into a 250 mL beaker containing ice cubes, and the pH was adjusted to 9-10 with Na2CO3. A large amount of yellow solid was produced at the bottom of the beaker, suction filtered, washed with water several times to neutral, and dried. After separation and purification by column chromatography (P: E = 3:1), the title compound was obtained.

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. 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guizhou University; Wu Jian; Xu Fangzhou; Wang Yanyan; Luo Dexia; Xue Wei; (37 pag.)CN108218848; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-79-0, 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 69045-79-0, name is 2-Chloro-5-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (S)-1-(phenyl-3-boronic acid)-ethyl]-carbamic acid tert-butyl ester (1.29 g, 4.86 mmol) and 2-chloro-5-Iodo-pyridine (1.4 g, 11.4 mmol) in ethyleneglycoldimethylether (25 mL) in a sealed tube were added cesium carbonate (4.75 g, 14.6 mmol) and water (5 mL). Argon was bubbled in to the above mixture for 10 min, and Pd(PPh3)4 (280 mg, 0.24 mmol) was added. The reaction mixture was stirred at 100 C. for 18 hand then cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2¡Á100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (785 mg, 69%) as yellow oil. [0147] 1H NMR (DMSO d6, 400 MHz): delta 1.28 (d, 3 H, J=6.8 Hz), 4.04 (q, 1 H, J=6.8 Hz), 7.4-7.45 (m, 2H), 7.5-7.55 (m, 1H), 7.61 (d, 1H J =7.8 Hz,), 7.72 (s, 1H), 8.15 (dd, 1H, J=8.3, 2.5 Hz,), 8.73 (d, 1H, J=3.3 Hz).

According to the analysis of related databases, 69045-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wu, Yong-Jin; Sun, Li-Qiang; L’Heureux, Alexandre; US2004/110754; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 849020-87-7, 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.849020-87-7, name is 6-Hydroxy-4-(trifluoromethyl)nicotinic acid, molecular formula is C7H4F3NO3, molecular weight is 207.1068, as common compound, the synthetic route is as follows.

Diethyl chlorophosphate (0.045 ml, 0.312 mmol) was added to a solution of 6-hydroxy-4-(trifluoromethyl)nicotinic acid (0.065 g, 0.312 mmol) in pyridine, anhydrous (0.945 ml, 11.70 mmol) at room temperature under nitrogen. After stirring for lh, this solution was added to a vial containing 6-fluoro-4-(4- methylpiperazin-1-yl)-3′-(mo holinomethyl)-[l, -biphenyl]-3-amine (step 3 from (a): 0.030 g, 0.078 mmol) under nitrogen and the reaction was heated to 70C for 3 hours. The pyridine was removed under reduced pressure and LCMS of the residue (dissolved in DCM, MeCN and MeOH) indicated complete conversion to the desired product. The mixture was loaded onto celite purified by flash chromatography [0.5-10% DCM/MeOH + 1% NH4OH] to methylpiperazin-1-yl)-3′-(mo holinomethyl)-[l,Gamma- biphenyl]-3-yl)-6-oxo-4-(trifluoromethyl)-l,6-dihydropyridine-3-carboxarnide (0.024 g, 0.042 mmol, 53.6% yield) as a clear film. NMR (500 MHz, DMSO-d6) delta = 9.53 (s, 1H), 7.94 (s, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.46 – 7.42 (m, 2H), 7.40 – 7.38 (m, 1H), 7.32 (d, J=7.3 Hz, 1H), 7.08 (d, J=12.5 Hz, 1H), 6.81 (s, 1H), 3.60 – 3.57 (m, 4H), 3.53 (s, 2H), 2.93 (br. s., 4H), 2.38 (br. s., 4H), 2.24 (s, 3H); LCMS [M+H]+ 574 g/mol.

The chemical industry reduces the impact on the environment during synthesis 849020-87-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem