Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 65515-39-1, 2-Methoxy-4,6-dimethylnicotinonitrile, 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, COA of Formula: C9H10N2O, blongs to pyridine-derivatives compound. COA of Formula: C9H10N2O

Example 8: (2-Methoxy-4,6-dimethylpyridin-3-yl)methanamine To a slurry solution of aluminum (III) lithium hydride (234 mg, 6.17 mmol) in diethyl ether (2 ml_) was added a saturated solution of 2-methoxy-4,6- dimethylnicotinonitrile (500 mg, 3.08 mmol) in ether (5 ml_) and stirred at room temperature for 1 h. After completion of the reaction, minimum amount of water was carefully added and the crude product obtained was extracted with hot benzene / toluene and concentrated. Resulting oily compound was distilled at 0.5 mm vacuum at 95-100 SC to obtain the title compound. Yield: 300 mg (58.66 %); 1H NMR (DMSO-d6, 300 MHz): delta 6.53 (s, 1 H), 3.92 (s, 3H), 3.76 (s, 2H), 2.36 (s, 3H), 2.27 (s, 3H); MS (ESI+): m/z 166.9 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65515-39-1, 2-Methoxy-4,6-dimethylnicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GUPTE, Amol; ROYCHOWDHURY, Abhijit; JADHAV, Ravindra, Dnyandev; KANDRE, Shivaji, Sadashiv; KADAM, Kishorkumar, Shivajirao; CHAVAN, Sambhaji; GADEKAR, Pradip, Keshavrao; GUHA, Tandra; WO2014/155301; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 851607-27-7, name is 5-Bromo-4-chloro-2-methoxypyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Bromo-4-chloro-2-methoxypyridine

[0848] To a stirred mixture of compound 3 (4 g, 18.1 mmol), compound 4 (4.52 g 21.72 mmol), and K2C03 (5 g, 36.2 mmol) in DME/H20 (48 mL,v/v=5/i) was added Pd(dppf)C12 (668 mg, 0.91 mmol) under N2 protection. The reaction mixture was degassed with nitrogen again and refluxed overnight. The mixture was concentrated, diluted with H20 and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (PE/EA=2/1) to give compound 5 (2.8g, 69% yield) as a pale yellow solid.

The synthetic route of 851607-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1228880-68-9, Methyl 3-bromo-5-methylpicolinate, 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, Quality Control of Methyl 3-bromo-5-methylpicolinate, blongs to pyridine-derivatives compound. Quality Control of Methyl 3-bromo-5-methylpicolinate

j0352] To a sealed tube containing methyl 2-chloro-5-me- thylnicotinate (CAS 65 169-43-9) (745 g, 4.01 mmol), Cul (38 mg, 0.2 mmol), LiC1 (169 g, 4.01 mmol), and Pd(PPh3)4 (231 g, 0.2 mmol) in toluene (15 mE) was added 2-(tributyl- stannyl)pyrimidine (1.5 mE, 4.4 mmol), and the reaction mixture was heated at 120 C. overnight. The reaction mixture was diluted with water and extracted with DCM. The combined organic layers were dried over Mg504, filtered and evaporated. Purification via silica gel chromatography (0-50% EtOAc in hexanes) gave the title compound (494 g, 52%). Prepared analogous to intermediate A-66, step Asubstituting methyl 2-chloro-5-methylnicotinate with methyl3-bromo-5-methylpicolinate. MS (ESI) mass calcd. forC,2H,,N302, 229.1; mlz found 230.0 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1228880-68-9, Methyl 3-bromo-5-methylpicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; COATE, Heather R.; DVORAK, Curt A.; FITZGERALD, Anne E.; LEBOLD, Terry P.; PREVILLE, Cathy; SHIREMAN, Brock T.; (473 pag.)US2016/46640; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1839-17-4 , The common heterocyclic compound, 1839-17-4, name is N4-Methylpyridine-3,4-diamine, molecular formula is C6H9N3, 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.

PREPARATION 7 Preparation of 1-methyl-2(3H)-oxo-imidazo-[4,5-c]pyridine 3-Amino-4-methylaminopyridine was reacted in the manner similar to that described in Preparation 6 to give the title compound. m.p.: 263-265 C. IR (KBr,cm-1): 2739; 1715; 1624. NMR (D2 O): 8.18(1H,s); 8.13(1H,d, J=5.3HZ); 7.1(1H,d, J=5.3Hz); 3.27(3H,s).

The synthetic route of 1839-17-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheil Foods & Chemicals, Inc.; US5281589; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. Product Details of 887707-23-5

A mixture of compound 12a2 (115 7 g, 400 mmol) and PhPOCI2 (668.6 g, 343 mmol) under N2 is stirred at 136C overnight, then cooled to room temperature and added slowly to 3 L of crushed ice. The aqueous mixture is adjusted to pH 6 and filtered. The aqueous filtrate is extracted with DCM (3 L) then the organic phase is washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated to provide chloropyridine 12a3.

The synthetic route of 887707-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/18657; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1000025-07-9, 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. 1000025-07-9, name is Vadadustat, molecular formula is C14H11ClN2O4, 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.

Vadadustat (0.5g), caffeine (0.35g) and acetonitrile (5mL) were charged in a RBF at 25±5C. The reaction mass was maintained under stirring at 25±5C for 16 hours. The product obtained was filtered and dried under vacuum for 3 hours at 40C. The solid obtained was identified as 1 :1 co-crystal of Vadadustat Caffeine. Yield: 0.55g

According to the analysis of related databases, 1000025-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MYLAN LABORATORIES LIMITED; JETTI, Ramakoteswara Rao; PILLI, Narasimha Murty; PATHURI, Srinivasarao; GOLIVI, Ramamohana Rao; JAYACHANDRA, Sureshbabu; (36 pag.)WO2020/75199; (2020); 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. 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Chloro-3-fluoroisonicotinic acid

Step A: A mixture of 2-chloro-3-fluoroisonicotinic acid (2.0 g, 10.0 mmol) in thionyl chloride (42 mL) was heated to 80 0C. The homogenous solution was stirred for 2 hours, concentrated under reduced pressure, and pumped dry on high vacuum overnight to give crude 2-chloro-3-fluoroisonicotinoyl chloride. Crude 2-chloro-3-fluoroisonicotinoyl chloride (1.04 g, 5.4 mmol) was added to a stirred solution of JV-(3-amino-2-chloro-4-fluorophenyl)-7V-(4- methoxybenzyl)propane-l -sulfonamide (2.08 g, 5.4 mmol) in anhydrous CHCl3 (15 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched by adding sat. aqueous NaHCO3 solution, followed by extraction with DCM (3X). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified using flash chromatography (gradient elution, solvent: 0-50% ethyl acetate in heptanes) to afford 2-chloro- LambdaL(2-chloro-6-fluoro-3-(N-(4-methoxybenzyl)propylsulfonamido)phenyl)-3- fluoroisonicotinamide (2.75 g, 94%). 1H NMR (500 MHz, DMSO-^6) delta 10.67 (s, IH), 8.44 (d, IH), 7.71 (t, IH), 7.35 (m, 2H), 7.13 (t, 2H), 6.82 (dd, 2H), 4.81 (d, IH), 4.63 (d, IH), 3.70 (s, 3H), 3.37 – 3.20 (m, 2H), 1.80 (d, 2H), 1.01 (dt, 3H). LC/MS: m/z 544.1 [M+l].

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, 628691-93-0, 2-Chloro-3-fluoroisonicotinic acid.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25938; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 39856-57-0, 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.39856-57-0, name is 2,6-Dibromopyridin-3-amine, molecular formula is C5H4Br2N2, molecular weight is 251.91, as common compound, the synthetic route is as follows.

Example 146 (Method N); N-(5-(3-(4-methoxyphenylsulfonamido)phenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide; Step 1. N-(5-bromothiazolor5,4-blpyridin-2-yl)acetamide; 2,6-dibromopyridin-3-amine (4.235 g, 16.8 mmol) was dissolved in acetone and acetyl isothiocyanate(1.85 ml, 21.0 mmol) was added. The flask was fit with a reflux condensor and placed in a preheated oil bath (65 – 70 C) and stirred under nitrogen for 2.5 hours. Then, the reaction was cooled to room temperature, poured into water, and filtered. The solid was washed with water, saturated sodium bicarbonate, and water again, and then collected and dried under high vacuum to afford N-(5- bromothiazolo[5,4-b]pyridin-2-yl)acetamide (5.54 g, Yield > 100%).MS (ESI pos. ion) m/z: 272 (MH+, 79Br), 274 (MH+, 81Br). Calculated exact mass for C8H6BrN3OS 271 (79Br), 273 (81Br).

Statistics shows that 39856-57-0 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromopyridin-3-amine.

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15103-48-7 , The common heterocyclic compound, 15103-48-7, name is Pyridine-2-sulfonic acid, molecular formula is C5H5NO3S, 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 dried Schlenck tube was charged with pyridine sulfonicacid (PySO3H,0.342 mmol) and KOtBu (0.342 mmol). Afteraddition of methanol, the reaction mixture was allowed to stirfor 30min then [RuCl2(p-cymene)]2 (0.1 g, 0.163 mmol)wasadded. The reaction mixture was stirred under nitrogen for 24h. The yellow suspension became a clear red solution withina few minutes. As the reaction progress, the solution becamecloudy then an orange-yellow solid appeared. The solid wascentrifuged and washed with diethyl ether (2 x 10 mL).The additional compound was obtained from the supernatantby subsequently drying, then dissolving the residuein dichloromethane followed by precipitation with hexane.Orange yellowsolid; yield: 106 mg (76%); Anal.Calcd. forC15H18ClNO3RuS:C41.96;H4.22;N3.26; S 7.45. Found:C41.86;H4.11;N3.58; S 7.24. FTIR (KBr, cm-1): 3051, 2974,1591, 1288, 1436; 1HNMR(CDCl3, delta): 8.76 (d, 1H, J= 5.1),8.01 (m, 1H), 7.88 (d, 1H, J=7.5), 7.57 (t, 1H), 5.78 (d, 1H, J=5.7), 5.69 (d, 1H, J= 5.7), 5.59 (d, 1H, J 6.0), 5.49 (d, 1H, J=6.0), 3.05 (m, 1H), 2.22 (s, 3H), 1.36 (t, 6H, J=7.2); 13CNMR(CDCl3, delta): 157.34, 153.57, 140.57, 127.84, 122.79, 103.97,97.65, 82.10, 81.92, 81.64, 80.54, 30.96, 22.91, 21.65, 18.39;ESI-MS: 394.0051 (M-Cl)+ calculated for C15H18NO3RuS,found 394.0026.

The synthetic route of 15103-48-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Keisham S; Sawant, Sneha G; Kaminsky, Werner; Journal of Chemical Sciences; vol. 130; 9; (2018);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6515-09-9, 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. 6515-09-9, name is 2,3,6-Trichloropyridine. A new synthetic method of this compound is introduced below.

Step A. (3,6-dichloro-pyridin-2-yl)-acetic acid ethyl ester Malonic acid t-butyl ester ethyl ester (7.1 mL, 36 mmol) was added via syringe over one minute with swirling to a frozen mixture of NaH (968 mg, 38.3 mmol) in DMSO (10 mL) at 0 C. The ice bath was removed and the mixture was stirred at rt for 15 min, and then at 115 C. for less than a minute until H2 evolution had subsided, and was then allowed to cool to rt. A solution of 2,3,6-trichloropyridine (3.26 g, 17.9 mmol) (J. Chem. Soc. C: Organic 1375, 1970) in DMSO (12 mL) was added, and the reaction stirred at 115 C. for 4 h. The reaction was then cooled to rt, shaken with 0.5 M NaH2PO4 (100 mL), and extracted with ether (1*50 mL; 2*25 mL). The organic layers were combined, washed with brine (1*20 mL), dried (Na2SO4), and concentrated under high vac at 95 C. to give a mixture of dichloro-pyridin-2-yl-malonic acid tert-butyl ester ethyl ester regioisomers as a clear amber oil (6.40 g) that was immediately used in the next step without further purification or characterization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6515-09-9, 2,3,6-Trichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Player, Mark R.; Lu, Tianbao; Hu, Huaping; Zhu, Xizhen; Teleha, Christopher; Kreutter, Kevin; US2007/225282; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem