Category: pyridine-derivatives

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. 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. 115473-15-9

Example 16Purification of 5,6,7,7a-tetrahydro-4H-thieno [3,2-c]-pyridin-2-one hydrochloride Compound of Formula-12b50 gms of crude 5,6,7,7a-tetrahydro-4H-thieno [3,2-c]-pyridin-2-one hydrochloride compound of formula-12b obtained in example-15 is taken in methylene chloride (50 ml) and methanol (50 ml). Heated the reaction mixture to 40-45 C. and stirred for 30 min at same temperature. Cooled the reaction mixture to 25-30 C. and stirred for 1 hour. Filtered the solid and washed with methylene chloride. Dried the compound to get the pure title compoundYield: 45 gms.

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, 115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride.

Reference:
Patent; Satyanarayana Reddy, Manne; Thirumalai Rajan, Srinivasan; Eswaraiah, Sajja; Rama Subba Reddy, Karamala; Kondal Reddy, Bairy; Venkat Reddy, Ghojala; US2012/202066; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

52334-81-3, 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. 52334-81-3, name is 2-Chloro-5-trifluoromethylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1; Preparation of 2-cyano-5-trifluoromethylpyridine; To 150ml N,N-dimethylformamide solution containing 15.0 g of 2-chloro-5-trifluoromethylpyridine were added 19.4 g of zinc cyanide and 9.6 g of tetrakistriphenylphosphine palladium, and the mixture was stirred under nitrogen atmosphere at 80C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature by allowing to stand, poured into 300 ml of dil. aqueous ammonia, and extracted with 300 ml of diethyl ether. The organic layer was washed with 200 ml of a saturated saline solution, then dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue was purified by distillation under reduced pressure (96.0 to 99.0C/40 mmHg) to obtain 10.9 g of the the objective product as white crystals. Melting point: 36.0 to 38.0C 1H NMR (CDCl3, Me4Si, 300MHz) delta 9.00 (bs, 1H), 8.13 (dd, J=8.3, 2.1Hz, 1H), 7.87 (d, J=8.3Hz, 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 52334-81-3, 2-Chloro-5-trifluoromethylpyridine.

Reference:
Patent; Nissan Chemical Industries, Ltd.; EP1671941; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-18-8 ,Some common heterocyclic compound, 5470-18-8, molecular formula is C5H3ClN2O2, 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.

Step 1: (3-Nitropyridin-2-yl)phenylamine A mixture of 2-chloro-3-nitropyridine (3.49 g, 22.0 mmol), phenylamine (2 mL, 22.0 mmol) and Et3N (3.1 mL, 22.0 mmol) in NMP (7 mL) was stirred at 100 C. for 1.5 h under a nitrogen atmosphere. Additional amounts of Et3N (0.2 mL) and of phenylamine (0.1 mL) were added and the stirring was continued for further 30 min. The mixture was then partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 10-100% DCM in pentane) affording (3-Nitropyridin-2-yl)phenylamine as a red crystalline solid (2.49 g, 58%). LCMS: RT 3.53 min [M+H]+ 216.0.

According to the analysis of related databases, 5470-18-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Heald, Robert; Price, Stephen; Safina, Brian; Savy, Pascal Pierre Alexandre; Seward, Eileen Mary; Sutherlin, Daniel P.; Waszkowycz, Bohdan; US2012/202785; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

73583-39-8, A common compound: 73583-39-8, name is 3-Bromo-5-chloropyridine,molecular formula is C5H3BrClN, 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.

Example 22: Synthesis of 2-Chloro-4-(5-chloro-4-hydroxymethyl-pyridin-3-yl)- b nzonitrileStep 1: 3-Bromo-5-chtoro-pyridine-4-carbaldehyde (22a)n-BuLi (11.25 ml_, 1.6 M, 18 mmol) was added dropwise to a solution of diisopropylamine (2.78 mL, 19.5 mmol) in THF(60mL) at -78C under N2. The resulting mixture was warmed up to -4CTC and stirred for 10 min and recooled to -78C. A solution of 3-bromo-5- chloropyridine (2.89 g, 15 mmol) in THF was added dropwise at this temperature. After 30 min, DMF was added dropwise and the resulting mixture was stirred for another 30 min. the reaction was quenched with saturated NH4CI solution, and warmed up to room temperature. After concentration, the residue was dissolved in EtOAc and washed with saturated NaHC03 solution. After dying over Na2S04, filtration and concentration, the residue was purified by I SCO (40g) column (0-30% EtOAc/Heptane) to give slightly yellow crystal (1.91g). ESI-MS m/z: 253.8 [M+1 +MeOH]+, Retention time 1.07min. -NMR (CDCI3, 400 MHz) delta 8.65 (s, 1 H), 8.76 (s, 1 H), 10.32 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 73583-39-8.

Reference:
Patent; NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien; WO2011/61168; (2011); A1;,
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 2637-34-5, name is 2-Mercaptopyridine. This compound has unique chemical properties. The synthetic route is as follows. 2637-34-5

A 1.0 M solution of HCI (45 mL) and DCM (45 mL) was cooled to -10 C and pyridine-2-thiol (1 .0 g, 9.0 mmol) added. After 10 min, NaOCI (6% solution, 47 mL, 3.3 eq.) was added drop-wise over 5 min and stirring continued at -10 C for 10 min. The organic phase was separated, dried using Na2S04 and filtered. The resulting solution was added drop-wise to a pre-cooled solution of sat. methanolic ammonia and DCM (1 : 1 , 40 mL) at 0 C then allowed to warm to ambient temperature and stirred until completion, typically 2 h. The solvent was removed in vacuo to give a white solid which was dissolved in hot EtOAc and filtered to remove solid impurities. The solvent was removed in vacuo and recrystallized with EtOAc-hexanes to give the titled compound as a yellow solid (0.5 g, 35%). 1 H NMR (300 MHz, DMSO-d6) delta = 8.70 (ddd, J = 4.7, 1 .7, 0.9 Hz, 1 H), 8.05 (td, J = 7.7, 1 .7 Hz, 1 H), 7.91 (dt, J = 7.9, 1 .1 Hz, 1 H), 7.62 (ddd, J = 7.6, 4.7, 1 .2 Hz, 1 H), 7.45 (s, 2H).

Statistics shows that 2637-34-5 is playing an increasingly important role. we look forward to future research findings about 2-Mercaptopyridine.

Reference:
Patent; THE UNIVERSITY OF QUEENSLAND; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH NEAR DUBLIN; O’NEILL, Luke; COLL, Rebecca; COOPER, Matt; ROBERTSON, Avril; SCHRODER, Kate; (379 pag.)WO2016/131098; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

624-28-2 , The common heterocyclic compound, 624-28-2, name is 2,5-Dibromopyridine, molecular formula is C5H3Br2N, 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.

Step 1: 5-Bro -2-methoxypyridine A mixture of 2,5-dibromopyridine (5.5 g, 23.2 mmol) and NaOMe (3.76 g, 69.6 mmol) in MeOH (60 mL) was heated at 70C for 1 hour and then allowed to cool to room temperature. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layers were dried over Na2S04 and concentrated under reduced pressure to give a pale yellow volatile oil (2.5 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): delta 8.26 (s, 1H), 7.87 (dd, 1H), 6.81 (d, 1H), 3.82 (s, 3H).

The synthetic route of 624-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENDO PHARMACEUTICALS INC.; SMITH, Roger, Astbury; KETHIRI, Raghava, Reddy; KRISTAM, Rajendra; LAPING, Nicholas, James; VENKATESHAPPA, Chandregowda; KULKARNI, Bheemashankar; DEVRAJ, Rajesh; DEWANG, Purushottam; WO2013/49559; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5350-93-6, 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. 5350-93-6, name is 6-Chloropyridin-3-amine, the common compound, a new synthetic route is introduced below.

Sodium nitrite (3.45g, 0.05mol) was added portion wise to a stirred solution of 6- chloro-pyridin-3-ylamine (6.4g, 0.05mol) in acetic acid (56ml) and HCl (cone)(9.92ml) while maintaining the temperature below 15¡ãC. This solution was then added drop wise to a stirred solution of sulfur dioxide (17.2g, 0.27mol), copper (II) chloride (1.85g, 0.01 lmol) and water (2.2ml) in acetic acid (37ml) at 5¡ãC. The reaction mixture was allowed to warm to room temperature and poured over ice water and stirred for a further 15min. The resultant precipitate was collected by filtration, washed with water and dried overnight in a vacuum oven to give 6- chloro-pyridine-3-sulfonyl chloride (6.41g, 60.5percent yield); (400 MHz; d6-DMSO) 8.54 (IH, d), 7.96 (IH, dd), 7.50 (IH, d).

Statistics shows that 5350-93-6 is playing an increasingly important role. we look forward to future research findings about 6-Chloropyridin-3-amine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/49605; (2008); 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. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, 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. 571188-59-5

Toluene (432.0 mL) and 4-(6-amino-pyridine-3-yl)-piperazine-l -carboxylic acid tert-butyl ester (34.3g, 0.123 moles) were charged into 2L 4N RB flask under nitrogen atmosphere at 30¡À5C and stirred for 5-10 min to get brown colored suspension. Reaction mass was cooled to 0¡À5C. Lithium hexamethyldisilazane 1M solution in THF (259.0 mL, 0.258 moles) was added dropwise to the reaction mass through addition funnel by maintaining the reaction mass temperature at 0 ¡À5C. And stirred the reaction mass for 10-15 min at 0 ¡À 5Cto get clear brown colored solution. Add the solution of 2-chloro-7-cyclopentyl-N,N-dimethyl-pyrrolo[2,3-d]pyrimidine- 6-carboxamide (36.0g, 0.123 moles) in 324.0 mL of toluene dropwise to the reaction mass through addition funnel at 0 ¡À5C. Reaction mass temperature was raised to 25- 35C and stirred for lh for reaction completion. (0107) After completion of reaction (by TLC), solvent was distilled off on rotavapor under vacuum at 55-60C to get the brown colored solid. DM water (360.0 mL) and aq. sodium bicarbonate solution (36.0g of sodium bicarbonate was dissolved in 720.0 mL of DM water) were added to the above solid and stirred for 10-15 min. Then methylene chloride (720 mL) was charged to the above solution and stirred for 5-l0min. Layers were separated. Organic layer washed with DM water (720 mL) and layers Separated. Solvent was distilled off from organic layer completely under vacuum at 45-50C on rotavapor to obtain brown colored solid. The solid was leached with methanol (180 mL) at 30 ¡À 5C to afford title compound as pale brown colour solid. Weight of the product: 57.0g (86.6% by theory). Purity by HPLC > 98.0%. (0108) H1 NMR (DMSO-d6): d 9.412 (S, 1 H), 8.167-8.190 (d, 2 H), 8.02-8.03 (d, 1 H), 7.449-7.479 (dd, 1 H), 6.603 (S, 1 H), 4.690-4.778 (m, 1 H), 3.472-3.484 (d, 4 H), 3.062-3.073 (d, 10H), 2.413-2.465 (m, 12 H), 1.92-1.991 (m, 4 H), 1.427-1.65 (m, 10H); Mass m/z (M+l): 535.25

The chemical industry reduces the impact on the environment during synthesis 571188-59-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NATCO PHARMA LIMITED; ARUNKUMAR, Thiriveedhi; SWAPNA, Kondaveeti; SATHISH, Thumati; NARESH, Ghanta; JANAKI RAMA RAO, Ravi; DURGA PRASAD, Konakanchi; PULLA REDDY, Muddasani; VENKAIAH CHOWDARY, Nannapaneni; (36 pag.)WO2019/142206; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some common heterocyclic compound, 504-29-0, molecular formula is C5H6N2, 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.504-29-0

To a solution of 2-aminopyridine (50.0 g, 531 mmol) in methylene chloride (500 mL) were added triethylamine (81.4 mL, 584 mmol) and pivaloyl chloride (71.9 mL, 584 mmol) at 0 C., which was stirred for 4 hours and 30 minutes at room temperature. The reaction solution was partitioned into water and methylene chloride. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. To a solution of the resulting residue in methanol (300 mL) was added potassium carbonate (73.4 g, 531 mmol) at 0 C., which was stirred for 90 minutes at room temperature. The reaction solution was partitioned into water and ethyl acetate at room temperature. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. Heptane (300 mL) was added to the residue, and the precipitated solids were filtered to obtain the title compound (80.2 g, 85%). The filtrate was then concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (12.2 g, 13%). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 1.22 (9H, s), 7.06-7.09 (1H, m), 7.72-7.77 (1H, m), 8.01-8.03 (1H, m), 8.29-8.31 (1H, m), 9.71 (1H, s).

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 504-29-0.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

108-99-6, 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. 108-99-6, name is 3-Methylpyridine, molecular formula is C6H7N, 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.

A 1000 mL four-neck bottle was placed in an ice water bath.Add 500g (content 99.5%,After the moisture content of 0.02%) 3-methylpyridine,Turn on the agitation,The dry hydrogen chloride gas (85g/h) is introduced under normal pressure.Water bath temperature control 0 C,Reacting in a dry anhydrous state,After all the white solid hydrochloride is formed,Stop stirring and continue to pass hydrogen chloride gas.The solid begins to dissolve,After introducing hydrogen chloride gas for 9 hours, 1265 g of liquid 3-methylpyridine hydrochloride was obtained (quantitative 3-methylpyridine content was39.53%).Transfer the above hydrochloride to a 2000 mL four-necked flask and place in an oil bath.After the stirring is started and the temperature is raised to 125 C, the chlorine gas after drying is started.Ventilation speed 50g/h,After 8h, the gas phase detection result was 3-methylpyridine: 3-chloromethylpyridine = 45:52 (gas phase qualitative ratio),Stop the chlorine and cool down to 110 C, at this temperature,Distilled under reduced pressure at a pressure of -0.08 MPa,A total of 236 g of distillate was obtained.Is unreacted 3-methylpyridine,The quantitative 3-methylpyridine content is 98.2%;The remaining bottom material is a light yellow solid.3-chloromethylpyridine hydrochloride,A total of 459.9g,The quantitative 3-chloromethylpyridine content is 73.88%,The yield was calculated to be 93.26%.

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. 108-99-6, 3-Methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Hong Sun Biochemical Co., Ltd.; Nanjing Hong Sun Co., Ltd.; Zhan Xinhua; Zhong Jingsong; Wang Fujun; Chen Honglong; Mu Dengyou; Yang Cheng; (5 pag.)CN108409641; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem