Day: November 23, 2020

115473-15-9 , The common heterocyclic compound, 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, molecular formula is C7H10ClNOS, 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.

To 4 mL of DMF was added compound 2 (0.20 g, 1.02 mmol), 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2 (4H)-one hydrochloride(5,6,7,7a-tetrahydrothieno[3,2-c] pyridin-2 (4H)-one hydrochloride, 0.29 ml, 1.53 mmol)1-ethyl-3-(3-dimethylaminopropyl)carbodiimide(1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 0.39 g, 2.04 mmol), N,N-diisopropylethylamine(N, N-diisopropylethylamine, a mixture of 0.36 mL, 2.04 mmol) in 40C was stirred for 4 hours. The mixture was concentrated under reduced pressure and purified by MPLC to give Oxo-DPide (1) in 10% yield.

According to the analysis of related databases, 115473-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Keimyung University; Seo Yeong-ho; (10 pag.)KR101937054; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 100704-10-7, name is (2-Chloropyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. 100704-10-7

Example N; To a stirred solution of 2-chloropyridine-4-methanol (143 mg, 1 mmol) in chloroform (10 ml) cooled in an ice bath under nitrogen atmosphere, was added triethylamine (210 mul, 1.5 mmol) and methanesulfonyl chloride (90 mul, 1.2 mmol) was added dropwise. After stirring for 1.1 hr., the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo for ca. 20 min. and mixed with (32) (297 mg, 1 mmol), powdered anhydrous potassium carbonate (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol). DMF (5 ml) was then added to the mixture at room temperature and stirred for overnight. After evaporation of DMF, the residue was dissolved in methanol-chloroform (1:9) and filtered through celite pad. The filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:2)) to afford 120 mg (28%) a white foam. Recrystallization from chloroform/ether/hexane resulted in a white solid. m.p. 206-207 C.; 1H-NMR (200 MHz, CDCl3) delta 1.13(3H, d, J=6.9 Hz), 1.23 (3H, d, J=6.9 Hz), 2.18 (1H, m), 2.43 (3H, s), 4.51 (1H, d, J=16.4 Hz), 5.06 (1H, d, J=16.4 Hz), 6.91-6.96 (2H, m), 7.66 (1H, s), 7.70 (1H, s), 7.88 (1H, s), 8.19 (1H, d, J=0.8 Hz, 5.5 Hz), 8.98 (1H, s); m/z (EI) 422(M+); HRMS (EI) Calcd, 422.114525, Found 422.114568.; Example BL; To a stirred solution of 2-chloro-4-pyridinemethanol (144 mg, 1 mmol) in chloroform (10 ml) at 0 C. (ice bath), was added triethylamine (210 mul, 1.5 mmol) and methanesulfonyl chloride (90 mul, 1.2 mmol). After stirring for 1.5 hr., the mixture was diluted with dichloromethane, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo and mixed with 3-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (323 mg, 1 mmol), anhydrous powdered potassium carbonate (138 mg, 1 mmol), lithium iodide (134 mg, 1 mmol). Anhydrous DMF (5 ml) was then added into the mixture and stirred for overnight at room temperature. The mixture was evaporated in vacuo. The residue was dissolved in methanol-dichloromethane (1:9), filtered through celite pad, and the filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, methanol:chloroform (2:98)) to afford 174 mg (38%) of a white solid. m.p. 242-244 C.; 1H-NMR (200 MHz, CDCl3/CD3OD) delta 1.12(3H, d, J=6.8 Hz), 1.22 (3H, d, J=6.8 Hz), 2.28 (1H, m), 2.40 (3H, s), 4.55 (1H, d, J=17.0 Hz), 4.97 (1H, d, J=17.0 Hz), 6.03 (1H, d, J=16.6 Hz), 6.97-6.99 (2H, m), 7.39 (1H, d, J=16.6 Hz), 7.55 (2H, s), 7.71 (1H, s), 8.15 (1H, d, J=5.8 Hz); m/z (EI) 448(M+).

Statistics shows that 100704-10-7 is playing an increasingly important role. we look forward to future research findings about (2-Chloropyridin-4-yl)methanol.

Reference:
Patent; Guo, Hongyan; Kim, Choung U.; Kim, Hae Soo; Lee, Chong-Kyo; Lee, Ill Young; Mitchell, Michael L.; Son, Jong Chan; Xu, Lianhong; US2008/70920; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A common compound: 97483-77-7, name is 5-Bromopicolinonitrile,molecular formula is C6H3BrN2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 97483-77-7

lOg of 2-cyano-5-bromopyridine prepared in the Preparation example 5 was dissolved in 100ml of dimethylformamide, 5.33g of sodiumazide, and 4.4g of ammoniumchloride were added to the solution at room temperature, and the solution was stirred at the temperature of 110C for 3 hours for reaction. The reaction mixture was added with water and then was extracted with ethyl acetate. The organic layer, thus separated, was washed with brine, dehydrated, filtrated and concentrated in vacuo thereby to obtain 10. 5g of the title compound. Yield 85%.

With the rapid development of chemical substances, we look forward to future research findings about 97483-77-7.

Reference:
Patent; DONG-A PHARM.CO.,LTD.; WO2005/58886; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 97483-77-7 as follows., 97483-77-7

A solution of 5-bromo-2-cyanopyridine (0.50 g, 2.73 mmol), bispinacolatodiboron (0.76 g, 3.0 mmol) and KOAc (0.34 g, 4.10 mmol) in 1 ,4-dioxane (10.0 mL) was degassed by flushing with nitrogen for 15 min. Tricyclohexylphosphine (0.091 g, 0.33 mmol) and tris(dibenzyledineacetone) dipalladium (0) (0.14 g, 0.14 mmol) was then added to the reaction mixture, which was again degassed by nitrogen for 15 min. The resulting reaction mixture was heated to 1000C for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was filtered through celite bed and the filtrate was concentrated to get the crude residue that was carried forward to the next step without further purification. MS: 231.10 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 97483-77-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PROLYSIS LTD; WO2009/74812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

504-29-0, 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. 504-29-0, name is Pyridin-2-amine, the common compound, a new synthetic route is introduced below.

General procedure: To a solution of aniline (1 mmol) in THF (10 mL) were added triethylamine (2 mmol) and pivaloyl chloride (1.2 mmol) at 0 C under inert atmosphere. After stirring for 12 h at room temperature, the triethylammonium chloride was removed by filtration and the filtrate was evaporated under reduced pressure to afford crude product which was washed with heptane to afford pure N-pivaloyl anilines.

Statistics shows that 504-29-0 is playing an increasingly important role. we look forward to future research findings about Pyridin-2-amine.

Reference:
Article; Kathiravan, Subban; Nicholls, Ian A.; Tetrahedron Letters; vol. 58; 1; (2017); p. 1 – 4;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-18-8, 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. 5470-18-8, name is 2-Chloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-(2-tert-butylphenoxy)-3-aminopyridine Intermediate 1a. 2-(2-tert-butylphenoxy)-3-nitropyridine: A solution of 2-chloro-3-nitropyridine (21.1 g, 133 mmol) in DMF (100 mL) was treated with 2-tert-butylphenol (23.5 mL, 153 mmol) and cesium carbonate (130 g, 398 mmol). The mixture was heated at 80 C. for 30 h. The reaction was cooled to rt and the mixture was poured into water (1 L) with stirring. The resulting yellow precipitate was filtered, washed with water, and recrystallized from ethanol to afford Intermediate 1a (32.8 g, 90% yield) as beige crystals; HPLC purity: 92%, 3.66 min (Method A); 1H NMR (400 MHz, CD3OD) 8 ppm 1.34 (s, 9H), 6.93 (m, 1H), 7.22 (m, 3H), 7.47 (m, 1H), 8.31 (dd, J=4.82, 1.75 Hz, 1H), 8.46 (dd, J=7.89, 1.75 Hz, 1H).

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 5470-18-8, 2-Chloro-3-nitropyridine.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293522; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

626-55-1, 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. 626-55-1, name is 3-Bromopyridine, molecular formula is C5H4BrN, 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.

Methyl 6-bromo-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate [0424] A 70% perchloric acid aqueous solution (12.9 mL) was added to a 1,4-dioxane solution (31 mL) of ethyl O-mesitylsulfonylacetohydroxamate (35.7 g) under an argon atmosphere under ice-cooling, and then the mixture was stirred for 30 minutes under ice-cooling. Ice water (360 mL) was added to the reaction solution, the precipitated solid was filtered off, the obtained solid was dissolved in dichloromethane (104 mL), and the solution was divided into layers. The organic layer was dried over anhydrous magnesium sulfate and filtered off. A dichloromethane solution (104 mL) of 3-bromopyridine (10 mL) was added to the obtained filtrate under ice-cooling, the mixture was stirred at room temperature for 1 hour, and the reaction solution was evaporated to obtain a crude product N-amino-3-bromopyridinium 2,4,6-trimethylbenzenesulfonate. Methyl phenylpropiolate (7.7 mL) and potassium carbonate (28.7 g) were added to an N,N-dimethylformamide solution (104 mL) of the crude product N-amino-3-bromopyridinium 2,4,6-trimethylbenzenesulfonate at room temperature under an argon atmosphere, and then the mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was evaporated and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 4:1) to obtain a title compound as a yellow powder (8.0 g).

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. 626-55-1, 3-Bromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; Kissei Pharmaceutical Co., Ltd.; SETO, Shigeki; UMEI, Kentaro; NISHIGAYA, Yosuke; TANIOKA, Asao; KONDO, Tatsuhiro; KONDO, Atsushi; TATANI, Kazuya; KAWAMURA, Naohiro; EP2669285; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding some certain compound to certain chemical reactions, such as: 5470-70-2, name is Methyl 6-methylnicotinate, 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 5470-70-2. 5470-70-2

Compound 1 (3g, 19.85mmol) was dissolved in MeOH (15ml) and NH2NH2-H2O (5.46g, 109.2mmol) was added. The mixture was stirred and raised to 900C for 2 hours. The mixture was concentrated and purified by chromatography to give desired product 2 as a white solid (2.Ig). Yield: 67percent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5470-70-2.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; HOLSWORTH, Dan; WAALER, Jo; MACHON, Ondrej; KRAUSS, Stefan; GOLDING, Louise; WO2010/139966; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

109-04-6, 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. 109-04-6, name is 2-Bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a 250 mL two-neck flask was added 2-bromopyridine (5.00 g, 31.7 mmol), and the mixture was stirred under a nitrogen atmosphere for 5 minutes, and then anhydrous tetrahydrofuran (150 mL) was further added. Next, the reaction flask was maintained at 78C using a dry ice/acetone bath, and n-butyllithium (14.0 mL; 2.5 M in n-hexane) was slowly added dropwise.After completion of the dropwise addition, the mixture was stirred at this temperature for 1 hour, and tributyltin chloride (10.3 mL, 38.0 mmol) was slowly added dropwise.The reaction was then allowed to slowly return to room temperature. After stirring for 12 hours, an appropriate amount of a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate.The combined organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was drained to give the tin-synthesized 2-(tributylstannyl)pyridine, which was not purified.

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 109-04-6, 2-Bromopyridine.

Reference:
Patent; NATIONAL TSING HUA UNIVERSITY; CHI, YUN; PALANISAMY, RAJAKANNU; MEGANATHAN, NANDAKUMAR; (65 pag.)TWI586662; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

462-08-8, 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. 462-08-8, name is Pyridin-3-amine, molecular formula is C5H6N2, 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.

50.0 g (0.53 mol) of 3-aminopyridine was added to 34.9 g of 35percent hydrochloric acid and stirred to prepare an aqueous hydrochloric acid solution of 3-aminopyridine. In addition, 35.9 g (0.52 mol, 0.98 mol equivalent to 3-aminopyridine) of sodium nitrite was added to 54.0 g of water and stirred to prepare an aqueous solution of sodium nitrite. 131 g of hydrochloric acid was placed in a 500 mL four-necked brown colben and cooled to -20 ¡ã C. An aqueous hydrochloric acid solution of 3-aminopyridine and an aqueous solution of sodium nitrite were simultaneously added dropwise to hydrochloric acid in a temperature range of -20 ¡À 2 ¡ã C. over 2 hours with stirring. After completion of the dropwise addition, the mixture was further stirred for 30 minutes in a temperature range of -20 ¡À 2 ¡ã C. to obtain an aqueous solution of pyridine-3-diazonium salt650 g of dichloromethane was placed in 1000 mL four-necked brown bottle and cooled to 0 ¡ã C., and 119 g (1.86 mol) of sulfur dioxide gas was blown into the solution to dissolve. 0.9 g (0.006 mol) of copper (II) chloride dihydrate was added and cooled to -5 ¡ã C., and an aqueous solution of pyridine-3-diazonium salt was added over a period of 1 hour at a temperature range of -5 ¡À 2 ¡ã C. Was added dropwise. After completion of the dropwise addition, the mixture was further stirred for 1 minute at a temperature range of -5 ¡À 2 ¡ã C. The copper catalyst was removed by filtration while maintaining the temperature of the reaction solution at -5 ¡À 5 ¡ã C., and then the organic layer and the aqueous layer were separated. It was extracted with 195 g of dichloromethane ¡Á 3 times at a temperature of -5 ¡À 5 ¡ã C. and mixed all together to obtain 1353 g of an organic layer. GC analysis of this organic layer revealed that the concentration of pyridine-3-sulfonyl chloride was 3.76percent by mass and the yield was 54.0percent. The obtained organic layer was washed with 50 g of water while maintaining the temperature at 3 ¡À 2 ¡ã C., and then dehydrated using 20 g of magnesium sulfate at room temperature. After removing the magnesium sulfate by filtration, the filtrate was concentrated under reduced pressure (30 to 35 ¡ã C.,> 67 kPa) to remove dichloromethane. Subsequently, distillation under reduced pressure (110 ¡ã C., 1.3 kPa) gave 49.0 g (0.276 mol, yield 52.1percent) of pyridine-3-sulfonyl chloride.

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. 462-08-8, Pyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tama Chemical Industry Co., Ltd.; Nobushima, Hirofumi; Kobayashi, Hitoshi; (9 pag.)JP2016/175885; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem