Day: August 3, 2021

Electric Literature of 499-51-4, 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. 499-51-4, name is 4-Hydroxypyridine-2,6-dicarboxylic acid. A new synthetic method of this compound is introduced below.

15 g of monohydric chelidamic acid (0.075 mol, I eq.) are dissolved in 120 mE of thionyl chloride under argon. The suspension is cooled to 00 C. and 3 mE DMF are added. The reaction mixture is then stirred for 12 hours with reflux. Volatiles are evaporated afier several toluene additions to remove the last traces of SOd2. The resulting yellowish solid is then dissolved in methanol and the mixture is refluxed for 12 hours to complete the reaction. After evaporation of the solvent, the residue is taken up by dichloromethane and washed successively with a saturated solution of NaHCO3, water and brine. The organic phase is then dried on Na2SO4, filtered and evaporated. Pure compound 12 is obtained by recrystallization in methanol to obtain 8.3of white crystalline powdet (R=44%). ?H-NMR (300 MHz, CDC13) oe (ppm)=8.29 (s,2H), 4.03 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,499-51-4, its application will become more common.

Reference:
Patent; ECOLE NORMALE SUPERIEURE DE LYON; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE CLAUDE BERNARD LYON I; COMMISSARIAT A L’ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; MAURY, Oliver; GIRARD, Eric; ENGILBERGE, Sylvain; RIOBE, Francois; (76 pag.)US2018/362550; (2018); 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C12H11NO2

g) tert-Butyl 8-(4-benzyloxy)-2-oxopyridin-1(2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (0.12 g, 0.33 mmol), 4-benzyloxy pyridinone (65 mg, 0.33 mmol), and Cs2CO3 (0.12 g, 0.38 mmol) were suspended in DMSO (2.0 mL), and the air was removed under vacuum for 15 min. The system was flushed with Ar, and 8-hydroxyquinoline (14 mg, 0.098 mmol) and copper iodide (74 mg, 0.39 mmol) were added to the suspension. The evacuation/Ar flushing process was repeated twice more, and the reaction mixture was heated at 133 C. for 18 h under N2. The mixture was cooled, diluted with 5:1 MeOH/NH4OH (25 mL), and the resulting solution was stirred at ambient temperature for 30 min. The reaction was further diluted with CH2Cl2 (75 mL), and the resulting solution was filtered through silica gel. The filtrate was concentrated under reduced pressure. The residue was diluted with CH2Cl2 and washed with H2O (1*25 mL) and brine (3*50 mL). The organic solution was dried over Na2SO4, filtered and concentrated to dryness. Flash chromatography (12 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 10 column volumes, increased to 50:50 over 20 column volumes and held for 5 column volumes) gave the title compound (88 mg, 54%) as a yellow foam: 1H NMR (500 MHz, CDCl3) delta 7.63-7.52 (m, 2H), 7.42-7.36 (m, 5H), 7.31 (d, J=7.5 Hz, 1H), 6.99 (d, J=7.0 Hz, 1H), 6.10-6.09 (m, 1H), 6.04-6.03 (m, 1H), 5.05 (s, 2H), 4.71-4.62 (m, 2H), 4.14-4.10 (m, 5H), 2.97-2.96 (m, 2H), 2.04-2.03 (m, 2H), 1.44-1.37 (m, 9H).

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, 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 29681-43-4, 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.29681-43-4, name is Methyl 4-methoxypyridine-2-carboxylate, molecular formula is C8H9NO3, molecular weight is 167.16, as common compound, the synthetic route is as follows.

b) Lithium aluminum hydride (16 ml of a 1.0 N solution in diethyl ether, 16 mmol) was added to a solution of methyl 4-methoxypicoline-2-carboxylate (2.70 g, 16 mmol) in diethyl ether (50 ml) at ambient temperature. The reaction was stirred for 1 hour, poured into an aqueous solution of Rochelle’s salt (250 ml) and the reaction mixture extracted with ethyl acetate (3*50 ml). Purification of the crude product by flash chromatography on silica gel, eluding with dichloromethane-ethyl acetate, yielded 2-(hydroxymethyl)-4-methoxypyridine (800 mg, 36% yield) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 29681-43-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AstraZeneca AB; US7081461; (2006); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 100910-66-5, 5-Methylnicotinaldehyde, 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, 100910-66-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of compound But-3-enenitrile (1.05 g, 15.74 mmol) in THF (30 mL) was added N2H4.H20 (0.826 g, 16.52 mmol) slowly at 0 C, and the resulting mixture was stirred room temperature for 16 hrs. Then to the reaction mixture was added 5 -methylnicotinaldehyde (2.0 g, 16.52 mmol). After stirring for 2.5 hrs, the reaction mixture was concentrated to dryness in vacuum. To the residue in n-Butanol (30 mL) was added MeONa (0.85 g, 15.74 mmol), and the mixture was heated to 120 C for 16 hrs. The reaction mixture was poured into iN HC1 (50 mL), and the mixture was extracted with EtOAc (100 mL x2). The aqueous layer was basified to pH = 14 and extracted with EtOAc (100 mL x2). The extracts were dried over Na2SO4, filtered and concentrated to give 3-methyl-1-((5-methylpyridin-3-yl)methyl)-1H-pyrazol-5-amine (0.75 g, yield: 24%) as brown oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100910-66-5, its application will become more common.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 626-60-8, 3-Chloropyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

General procedure: Biaryls 1; General Procedure for the Suzuki-Miyaura Couplingof Aryl ChloridesA stock solution of Pd source (2 mol%) with ligand (correspondingPd/L ratio) in freshly distilled CH2Cl2 (10 mL) was initially preparedwith continuously stirring at r.t. An array of Schlenk tubesequipped with a Teflon-coated magnetic stirrer bar were evacuatedand backfilled with N2 (3 cycles). The stock solution of Pd with ligand(0.5 mL, 0.1 mol% Pd, or please refer to the corresponding Pdloading from different entries) and Et3N (0.1 mL) were transferredto an array of Schlenk tubes via syringes. The diluted Pd complexsolution was stirred and warmed using a household hair drier forabout 1 to 2 min until the solvent started boiling. The solvent wasthen evaporated under high vacuum. Ar2BF3K (0.75 mmol, 1.5equiv) and base (1.5 mmol, 3.0 equiv) were added to an array ofSchlenk tubes. Each tube was carefully evacuated and backfilledwith N2 (3 cycles). Aryl chloride (0.5 mmol, 1.0 equiv) and H2O(1.5 mL) were added via syringe. This batch of Schlenk tube was resealedand magnetically stirred in a preheated 100 C oil bath. Afterthe completion of the reaction, the reaction tubes were allowed toreach r.t. EtOAc (~10 mL) and H2O (~3 mL) were added. The organiclayer was subjected to GC analysis. The filtrate was concentratedunder reduced pressure. The crude products were purified byflash column chromatography on silica gel (230-400 mesh) to affordthe desired product

At the same time, in my other blogs, there are other synthetic methods of this type of compound,626-60-8, 3-Chloropyridine, and friends who are interested can also refer to it.

Reference:
Article; Yuen, On Ying; Wong, Shun Man; Chan, Kin Fai; So, Chau Ming; Kwong, Fuk Yee; Synthesis; vol. 46; 20; (2014); p. 2826 – 2832;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1196146-82-3 ,Some common heterocyclic compound, 1196146-82-3, molecular formula is C5H3BrClNO, 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 solution of 5-bromo-2-chloropyridin-4-ol (200 g 0.960 mol, Intermediate 56) and sodium chlorodifluoroacetate (264 g, 1.73 mol) in DMF (1 L) was added dropwise to a 110-115 C. suspension of Cs2CO3 (469 g, 1.44 mol) in DMF (1 L), and the resulting mixture was stirred at 110-115 C. After the reaction went to completion, mixture was allowed to cool to 50-60 C., and then it was poured into ice water. The resulting mixture was extracted twice with MTBE, and the combined organic layers were washed with water and then concentrated. The concentrate was purified by distillation to afford the title compound as a colorless liquid (bp 75-78 C. at 1-2 mmHg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1196146-82-3, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Wolin, Ronald L.; Fourie, Anne M.; Xue, Xiaohua; (85 pag.)US2019/382350; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6602-32-0, 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. 6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, 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.

To a stirred solution of triphenylphosphine (6.31 g, 24.1 mmol) and DEAD (4.49, 25.8 mmol) in THF (30 mL) at 0 Cwas added a solution of 3 (3.10 g, 17.2 mmol) and 2-bromopyridin-3-ol 4 (3.44 g, 19.8 mmol) in THF (20 mL). The resulting luminous yellow solution was stirred under a nitrogen atmosphere at ambient temperature for 24 h at which all starting materials had been consumed. The solvent was removed, the residue was purified by flash chromatography on silica gel eluting with EtOAc/petroleum ether (1%-20%) to give 5 as light yellow liquid (4.97 g, 86%). 1H NMR (400 MHz, DMSO-d6) delta 8.06 (s, ArH, 1H), 7.92 (dd, J = 1.2, ArH, 4.4 Hz, 1H), 7.88 (d, J = 7.6 Hz, ArH, 1H), 7.72 (d, J = 7.6 Hz, ArH, 1H), 7.54 (t, J = 7.8 Hz, ArH, 1H), 7.45 (dd, J = 1.2, 8.0 Hz, ArH, 1H), 7.29 (dd, J = 4.8, 8.0 Hz, ArH, 1H), 5.84 (q, J = 6.4 Hz, CH, 1H), 3.86 (s, OCH3, 3H), 1.62 (d, J = 6.4 Hz, CH3, 3H). ESI-MS m/z: 336.6 and 338.5 [M+H]+.

According to the analysis of related databases, 6602-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tian, Yuanxin; Zhang, Tingting; Long, Lifan; Li, Zhonghuang; Wan, Shanhe; Wang, Guangfa; Yu, Yonghuan; Hou, Ju; Wu, Xiaoyun; Zhang, Jiajie; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 182 – 199;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84249-14-9, 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 84249-14-9, name is 2-Amino-4-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 4-bromopyridin-2-amine (3.11 g, 17.98 mmol) in CH2CI2 (60 mL) at 0 C was added acetyl chloride (1.406 mL, 19.77 mmol) and pyridine (1.745 mL, 21.57 mmol). The mixture was warmed to rt and stirred for 2 h. The reaction was quenched with water and diluted with EtOAc. The layers were separated. The organic layer was washed with water, brine, dried Na2S04) and concentrated under reduced pressure to obtain N-(4-bromopyridin-2-yl)acetamide (3.82 g, 17.05 mmol, 95% yield) as a white solid. The material was carried on without further purification. LCMS (ESI) m/e 215.0 [(M+H)+, calcd 215.0]; LC/MS retention time (method A): /R = 2.61 min.

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 84249-14-9, 2-Amino-4-bromopyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); 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. 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. Quality Control of 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride

[0091 ] In a four necked round bottomed flask, under nitrogen atmosphere, 1000 ml acetonitrile, 49.5 gm of 5,6,7, 7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one.HCl, 55 gm of sodium carbonate and 100 gm of Methyl (R)-2- (4-nitrophenylsulfonyloxy)-2(2- chlorophenyl)acetate were added and the mixture was heated to about 50C. After reaction, reaction mass was filtered, filtrate concentrated and concentrated mass was taken in dichloromethane, washed with water and concentrated under reduced pressure. The oily residue was treated with IPA.HC1 solution in isopropanol (IPA) and filtered to obtain the mixture of isomers as hydrochloride salt. To it sodium bicarbonate solution was added till pH turned alkaline. The product was then extracted in dichloromethane (MDC). The MDC layer was washed with water, dried and distilled to obtain the product as an oily residue. [0092] Ratio of (7aS,2’S)/(7aR,2’S)-isomers as per chiral HPLC : 53.62/46.38% : [0093] Example 2. Methyl (7aS,2’S)-2-(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydro thieno[3,2-c]-5-pyridin-2-one)acetate [0094] In a four necked round bottomed flask, under nitrogen atmosphere, 150 ml of ethyl acetate-methanol and 70 gm of mixture of isomers (Ratio of (7aS,2’S)/(7aR,2’S)-isomers = 53.62:46.38) was taken and warmed to dissolve, and stirred for 20 hours under room temperature, crystals obtained were filtered and the solid was dried to obtain 52 gm Methyl (S)-2(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydrothieno[3,2-c]-5-pyridin-2-one) acetate. Yield = 60%; Ratio of (7aS,2’S)/(7aR,2’S)-isomers as per chiral HPLC : 99.5:0.5. [0095] .H-NMR(DMSO-d6) spectra collected on a BRUKER 400MHz instrument has shown values given in table 2 corresponding to structure of formula II A free base below: [0096] Table 2: No. m- multiplet, s-singlet, d-doublet of doublet. Single crystal analysis data of material conforms to (7aS,2″S)-conl”iguration.

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; IPCA LABORATORIES LIMITED; KUMAR, Ashok; SOUDAGAR, Satish Rajanikant; NELLITHANATH, Thankachen Byju; SAHAL, Gaurav; MATHUR, Arpana Prashant; GAWADE, Sanjay Pandurang; BHADRA, Dinesh Kanji; MOJE, Devki; WO2013/1544; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1597-32-6, 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 1597-32-6, name is 2-Amino-6-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 20: 1-(4-Fluorophenyl)-/V-(6-fluoro-2-pyridinyl)-5-methyl-1H-1 ,2,3-triazole- 4-carboxamide; To a solution of 6-fluoro-2-pyridinamine (0.092 g, 0.822 mmol) in dry 1 ,4-dioxane (1 ml) was added dropwise trimethylaluminium (0.401 ml, 0.802 mmol) (2M solution in toluene). The solution was stirred at room temperature for 30 min. Then a solution of ethyl 1-(4-fluorophenyl)-5-methyl-1 H-1 ,2,3-triazole-4-carboxylate (Intermediate 2) (0.05 g, 0.201 mmol) in dry 1 ,4-dioxane (1 ml) was added at room temperature and the reaction was heated to 100 0C for 1.5 hours. The reaction was cooled to room temperature, quenched cautiously with water (0.06 ml), and stirred at room temperature for 10 min. Then, sodium sulphate (0.25 g) was added to bind the water and the mixture was stirred vigorously for 5 min. Dichloromethane was added and the mixture was stirred for an additional 10 min at room temperature. The solution was filtered and the solid was washed with dichloromethane. The filtrate was evaporated to afford a residue. The residue was partially dissolved in methanol, filtered and the solid washed with diethyl ether to afford a the title compound (44.5%); MH+= 316; 1HNMR (DMSO, 400 MHz): 2.57 (3H s), 6.96 (1 H m), 7.53 (2H t), 7.76 (2H m), 8.07 (2H m), 10.22 (1 H s).

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 1597-32-6, 2-Amino-6-fluoropyridine.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/115486; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem