Day: September 2, 2021

Synthetic Route of 144100-07-2, 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 144100-07-2, name is 2-Bromo-6-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydrogen (909.07 mg, 22.73 mmol, 60% purity) was dissolved in anhydrous THF (5 mL), the reaction was placed in an ice bath, replaced with nitrogen for 3 times, 2-bromo-6-fluoropyridine (2 g, 11.36 mmol), and 1-methylimidazolidinone (2.28 g, 22.73 mmol) were added at 0C, the mixture was stirred at 70C for 16 hours. Water (20 mL) was added to quench the reaction, then extracted with EA (3×20 mL), the organic phase was washed by saturated brine (20 mL), dried over anhydrous sodium sulfate, the filtrate was concentrated to give the crude product, the crude product was purified by column to give the 56-1. 1H NMR (400MHz, CDCl3) delta = 8.23 (d, J=8.5 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.05 (d, J=7.5 Hz, 1H), 4.10 – 3.93 (m, 2H), 3.53 – 3.40 (m, 2H), 2.95 – 2.85 (m, 3H), MS m/z:256.10 [M+H]+

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 144100-07-2, 2-Bromo-6-fluoropyridine.

Reference:
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-64-4, 2-Chloro-5-methylpyridine, 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, Formula: C6H6ClN, blongs to pyridine-derivatives compound. Formula: C6H6ClN

Triphenylphosphine (430 mg, 1 .64 mmol) was added to a solution of 2-chloro-5- fluorophenol (200 mg, 1 .37 mmol) in tetrahydrofuran (2 mL). The reaction mixture was cooled to 0 °C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (213 mg, 1 .64 mmol) was added, followed by DIAD (0.32 mL, 1 .6 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days, and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 10percent-50percent EtOAc-heptane gradient to give the title compound (264 mg, 64percent) as a yellow oil. 1H NMR (400 MHz, CDCI3) delta 2.50-2.61 (m, 2 H), 2.78 (ddd, J = 14, 7, 4 Hz, 2 H), 3.18-3.28 (m, 1 H), 3.76 (s, 3 H), 4.91 (quin, J = 7 Hz, 1 H), 6.49 (dd, J = 10, 3 Hz, 1 H), 6.63 (td, J = 8, 3 Hz, 1 H), 7.30 (dd, J = 9, 6 Hz, 1 H); LC-MS (LC-ES) M+H = 259, 261 (CI pattern).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-64-4, 2-Chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 152460-09-8 ,Some common heterocyclic compound, 152460-09-8, molecular formula is C16H13N5O2, 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.

N-(2-Methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine 5 (35g, 0.114mol) and stannous chloride dihydrate (128.5g, 0.569mol) were dissolved in a solvent mixture of ethyl acetate and ethanol (250mL, 10/1, v/v), and the reaction solution was refluxed for 4h. The solution was cooled to room temperature, washed with 10% aqueous sodium hydroxide solution, and concentrated to give N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine 6 (35g). Rf=0.45 (DCM/MeOH, 9:1). NMR was in agreement with the reference.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,152460-09-8, its application will become more common.

Reference:
Article; Peng, Zhenghong; Maxwell, David S.; Sun, Duoli; Bhanu Prasad, Basvoju A.; Pal, Ashutosh; Wang, Shimei; Balatoni, Julius; Ghosh, Pradip; Lim, Seok T.; Volgin, Andrei; Shavrin, Aleksander; Alauddin, Mian M.; Gelovani, Juri G.; Bornmann, William G.; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 623 – 632;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73290-22-9, Adding some certain compound to certain chemical reactions, such as: 73290-22-9, name is 2-Bromo-5-iodopyridine,molecular formula is C5H3BrIN, 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 73290-22-9.

To the solution of (2-methoxyphenyl)boronic acid (0.471 g, 3.1 mmol) in 1 ,4-dioxane(20 mL), 2-bromo-5-iodopyridine (1.lg, 3.87 mmol), potassium phosphate tribasic(2.46 g, 11 .61 mmol) and water (5 mL) was added. The reaction mixture wasdegasified for 10 mm under nitrogen before the addition of Pd(PPh3)4 (0.224 g, 0.194mmol) to it. The reaction mixture was then heated at 70C for 1 h. The reactionmixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na2SO4. The organic layer was concentrated under vacuo to yield crude product, which was purified by column chromatography to yield title compound (0.72 g, 87.09%) as a colourless liquid.LCMS: (M+H) = 264-266; 1H NMR: (ODd3, 300MHz) 68.43-8.44 (d, 1H), 7.65-7.68 (dd, 1H), 7.42-7.45 (d, 1H), 7.29-7.34 (t, 1H), 7.19-7.23 (m, 1H), 6.99-7.01 (d, 1H), 6.92-6.96 (m, 1 H), 3.75 (5, 3H).

According to the analysis of related databases, 73290-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58481-11-1, 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 58481-11-1, name is Methyl 2-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-chloroisonicotinate (0.996 g, 5.80 mmol), potassium carbonate (1.042 g, 7.54 mmol), 4,4,5,5-tetramethyl-2-(3-methyl-4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (1.66 g, 5.80 mmol) and PdCl2 (dppf) (0.105 g, 0.15 mmol) were mixed in methanol (20 mL) in two microwave vials. The vials were capped and heated at 100° C. for 10 min in a single node microwave reactor. The solution was partitioned between water and ethyl acetate. The organic layer was isolated, dried over Na2SO4, filtered through celite and the solvent was evaporated. Automated column chromatography using the Biotage equipment. Gradient eluation using heptane-ethyl acetate, 0percent to 50percent. Methyl 2-(3-methyl-4-(trifluoromethyl)phenyl)-isonicotinate (1.22 g, 71percent) was isolated. 1H NMR (600 MHz, cdcl3) delta 2.57 (s, 3H), 3.99 (s, 3H), 7.70 (d, 1H), 7.81 (dd, 1H), 7.91 (d, 1H), 7.98 (s, 1H), 8.29 (s, 1H), 8.84 (d, 1H).

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17228-69-2 ,Some common heterocyclic compound, 17228-69-2, molecular formula is C6H6ClNO, 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 suspension of 2-chloro-4-methoxypyridine (250 mg; commercial), 2-benzyloxy- 5-formylphenylboronic acid (455 mg; commercial), K2C03 (1.65 g) in water (3 mL) and DMF (12 mL) was degassed with nitrogen, treated with bis(triphenylphosphine)palladium(II) di chloride (48 mg) and heated for 3 h at 100C. The reaction mixture was evaporated under reduced pressure and the residue was partitioned between water and EA. The aq. layer was extracted with EA. The combined org. layers were washed with water and brine, dried over MgS04; evaporated under reduced pressure and purified by CC (Hept to Hept/EA 2:3) to yield a light yellow solid (309 mg; 60% yield). MSI (ESI, m/z): 320.1 [M+H+]; tR = 0.66 min.

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. 17228-69-2, 2-Chloro-4-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CREN, Sylvaine; FRIEDLI, Astrid; HUBSCHWERLEN, Christian; RUEEDI, Georg; ZUMBRUNN, Cornelia; WO2014/170821; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 769-28-8, Adding some certain compound to certain chemical reactions, such as: 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile,molecular formula is C8H8N2O, 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 769-28-8.

A 100 mL Teflon-sealed flask was charged with the 2-pyridone 1m(296 mg, 2.0 mmol), diaryliodonium salts 2r (1.695 g, 3.0 mmol, 1.5equiv), and Cs2CO3 (975 mg, 3.0 mmol, 1.5 equiv) under air atmosphere.DCE (20 mL) was then added to the flask. The reaction mixturewas stirred at 120 C until the 2-pyridone 1m was consumedcompletely (monitored by TLC). At this time, the solvent was removedin vacuo and the residue was purified by flash column chromatography(the crude residue was dry loaded on silica gel, 1:10 EtOAc/PE) toprovide the desired product 5; yield: 485 mg (83%); white solid; mp102-103 C.IR (film): 3073, 2922, 2229, 1600, 1449, 1327, 1179, 799 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.54-7.48 (m, 3 H), 7.39 (d, J = 7.2 Hz,1 H), 6.86 (s, 1 H), 2.54 (s, 3 H), 2.37 (s, 3 H). 13C NMR (100 MHz, CDCl3): delta = 126.8, 161.1, 155.1, 152.9, 132.3 (q, J =32.1 Hz), 129.9, 124.9, 122.2 (q, J = 269.1 Hz), 121.9 (q, J = 3.6 Hz),119.7, 118.8 (q, J = 3.6 Hz), 114.3, 95.3, 24.4, 20.2.HRMS (ESI): m/z (M + H)+ calcd for C15H12F3N2O: 293.0902; found:293.0891.

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. 769-28-8, 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Xiao-Hua; Ye, Ai-Hui; Liang, Cui; Mo, Dong-Liang; Synthesis; vol. 50; 8; (2018); p. 1699 – 1710;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 871836-51-0, 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.871836-51-0, name is 4-Chloro-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

To a solution of 4-chloro-IH-pyrazolo[4,3-clpyridine (100 mg, 0.6Smmoi) (3 mL) was added NaI-l (78 mg, 1.95 mmol, 60 wt% in oil) at 0C under N2. The mixture was stirred at 0C for 40 minutes. Mel (277 mg, 1,95 mmol) was added at 25C. The mixture wasstirred for another 2 hours. The mixture was quenched with saturated Ni-14C1 aqueous solution and extracted with ELOAc (20 mL x 3). The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by Prep-HPLC to give the title compound 56 (50.2 mg) as yellow oil, 57 (30 mg) as yellow oil. LRMS miz (M+H) 168.1, 170.1 found, 168.0, 170.1 required.

The chemical industry reduces the impact on the environment during synthesis 871836-51-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); 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. 52833-94-0, name is 2-Amino-5-bromonicotinic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 2-Amino-5-bromonicotinic acid

To a mixture of 2-amino-5-bromonicotinic acid (1 g, 4.61 mmol) and (1-(1-(tert- butoxycarbonyl)piperidin-4-yl)-1H-pyrazol-4-yl)boronic acid pinacol ester (2.6 g, 6.91 mmol) in 25 mL of 1,4-dioxane/ water (3/1) was added K2CO3 (1.9 g, 13.8 mmol) followed by Pd(PPh3)4 (0.26 g, 0.23 mmol). The reaction mixture was heated at 100 C for 3 h, cooled to room temperature, and partitioned between water and ethyl acetate. Water layer was separated and adjusted to pH value around 5. The precipitate was collected by filtration and triturated in mixture of methanol and water. The precipitate was filtered. The wet cake was dried to afford 1.5 g of the title compound. The crude product was used for the next step without further purification. MS (ESI, m/z): 388.1 [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, 52833-94-0, 2-Amino-5-bromonicotinic acid.

Reference:
Patent; DONG-A SOCIO HOLDINGS CO., LTD.; KIM, Hadong; RYU, Ki Moon; PARK, Seong Jin; YOON, Taeyoung; JANG, Mi Yeon; KIM, Jin Kwan; (419 pag.)WO2018/71343; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 588729-99-1, 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. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, molecular formula is C5H4BrClN2, 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.

c) N-(5 -bromo-2-chloro-3 -pyridinyl)benzenesulfonamide. To a stirred solution of 3-amino-5-bromo-2-chloropyridine (24 mmol) in dichloromethane (50 mL) was added pyridine (37 mmol) followed by benzenesulfonyl chloride (35 mmol) drop wise over 5 min. The reaction mixture was stirred at room temperature for 18 h and evaporated to dryness in vacuo. The residue was purified by flash chromatography on silica gel (15% hexanes/dichloromethane then 0-5% ethyl acetate in 15% hexanes/dichloromethane). During evaporation of the solvents the product precipitated. The resultant slurry was diluted with hexanes, filtered, and dried under vacuum to give the title compound (2.89 g, 34%) as a white solid. MS (ES) m/e 346.7 (M + H)+.

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 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/39140; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem