Pyridine-derivatives

Synthetic Route of 59-26-7, 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. 59-26-7, name is N,N-Diethylnicotinamide. A new synthetic method of this compound is introduced below.

General procedure: CoSO4·7H2O (0.005 mol, 1.41 g) and DENA (0.01 mol, 1.78 g) in separate beakers were dissolved in 50 mL of distilled water. The solutions of DENA and sodium 4-cyanobenzoate were added to the CoSO4 solution, respectively. The resulting clear solution was allowed to crystallize at room temperature. Pink single crystals were obtained after 1 week. The crystals were filtered off and washed with distilled water and dried at room temperature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59-26-7, N,N-Diethylnicotinamide, and friends who are interested can also refer to it.

Reference:
Article; Sertcelik, Mustafa; Oezbek, Fuereya Elif; Yueksek, Mustafa; Elmal?, Ayhan; Aydo?du, Oemer; Necefo?lu, Hacali; Hoekelek, Tuncer; Chemical Papers; (2020);,
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. 638218-78-7, name is 2-(6-Bromopyridin-2-yl)propan-2-ol. A new synthetic method of this compound is introduced below., Product Details of 638218-78-7

Into a lOOO-mL 3-necked round-bottom flask, was placed 6-(methylsulfanyl)-2-(prop-2-en-l-yl)-lH,2H,3H- pyrazolo[3,4-d]pyrimidin-3-one (20 g, 89.98 mmol, 1.00 equiv), 2-(6-bromopyridin-2- yl)propan-2-ol (24 g, 111.07 mmol, 1.23 equiv), 1,4-dioxane (500 mL), iodocopper (17.1 g, 89.79 mmol, 1.0 equiv), K2C03 (17.1 g, 122.83 mmol, 1.37 equiv). This was followed by the addition of methyl [2-(methylamino) ethyl] amine (10.8 mL) dropwise with stirring. The resulting solution was stirred overnight at 95C in an oil bath. The resulting mixture was cooled to room temperature. The mixture was then quenched by the addition of 100 mL of water. The resulting mixture was concentrated under vacuum. The residue was extracted with 3×500 mL of ethyl acetate and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5- 1:3). This resulted in 15 g (47%) of l-[6-(2-hydroxypropan-2-yl) pyridin-2-yl]-6-(methylsulfanyl)-2-(prop-2-en-l-yl)-lH,2H,3H- pyrazolo[3,4-d]pyrimidin-3-one as a white solid. LC-MS(ES, m/z) M+l=358

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, 638218-78-7, 2-(6-Bromopyridin-2-yl)propan-2-ol.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (0 pag.)WO2019/165204; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116355-16-9, 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. 116355-16-9, name is Imidazo[1,2-a]pyridine-6-carbaldehyde. A new synthetic method of this compound is introduced below.

General procedure: To a 2mL Eppendorf tube was added 10muL of the aldehyde stock solution in DMSO (0.1M, final concentration 10mM), 90muL of buffer (100mM phosphate buffer, 0.1mM PLP, 2M glycine, pH=7.0) and 2muL of a 10.16mg/mL enzyme solution in phosphate buffer (100mM, 1mM PLP, pH=7.0, 0.2mg/mL final protein concentration). The mixture was incubated at 40C and 1100rpm on an Eppendorf Thermomixer. After 1.5h, the reaction was quenched with 200muL ACN/MeOH (1:1), stirred for 5min at 1100rpm and centrifuged at 21,130 xg for 3min. The clear supernatant was analyzed using an UPLC monitoring method (see supplementary information).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116355-16-9, Imidazo[1,2-a]pyridine-6-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Ligibel, Mathieu; Moore, Charles; Bruccoleri, Robert; Snajdrova, Radka; Biochimica et Biophysica Acta – Proteins and Proteomics; vol. 1868; 2; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 106850-34-4 , The common heterocyclic compound, 106850-34-4, name is Imidazo[1,2-a]pyridine-6-carbonitrile, molecular formula is C8H5N3, 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.

An oven dried resealable Schlenk tube was charged with imidazo[1 ,2-a]pyridine-6- carbonitrile (Preparation 1 , 0.30 g, 2.1 mmol), N-benzyl-2-chloro-N-methylpyrimidin-4- amine (Preparation 31 , 0.24 g, 1.0 mmol), potassium acetate (0.21 g, 2.1 mmol) and Lambda/,Lambda/’-dimethylacetamide (3 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon then tetrakis(triphenylphosphine)palladium (0) (0.12 g, 0.10 mmol) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 150 C and the mixture was stirred overnight. The mixture was evaporated in vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgS04) and evaporated and the residue was purified by flash chromatography (99:1 to 98:2 dichloromethane/methanol) to give the title compound (0.105 g, 30%) as a pale brown solid.LRMS (m/z): 341 (M+1)+.1H-NMR delta (CDCI3): 3.22 (bs, 3H), 4.91 (bs, 2H), 6.40 (d, 1 H), 7.27 – 7.41 (m, 6H), 7.76 (dd, 1 H), 8.31 (d, 1 H), 8.59 (s, 1 H), 10.49 (bs, 1 H)

The synthetic route of 106850-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; MATASSA, Victor Giulio; WO2011/76419; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 156772-60-0, Adding some certain compound to certain chemical reactions, such as: 156772-60-0, name is 2,5-Dibromo-3-fluoropyridine,molecular formula is C5H2Br2FN, 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 156772-60-0.

7.1b. 5-bromo-2-[(tert-butyldimethylsilanyl)ethynyl]-3-fluoropyridine Under an argon atmosphere, 2.62 mL (13.811 mmol) of tert-butylethynyldimethylsilane was added to a solution of 3.20 g (12.56 mmol) of 2,5-dibromo-3-fluoropyridine, 5.22 mL of triethylamine (37.67 mmol), 59.8 mg (0.31 mmol) of CuI, and 220.3 mg (0.31 mmol) of bis(triphenylphosphane)palladium (II) chloride in 30 mL of absolute THF at 15 C. and the mixture was stirred for 2 hours at RT. 1 mL of tert-butylethynyldimethylsilane was added and the mixture was again stirred for 1 hour at RT. The reaction mixture was evaporated down in vacuo and the residue was taken up in EtOAc. The organic phase was washed with semisaturated aqueous sodium bicarbonate solution, 5% aqueous ammonia, and water, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, PE/DCM 9:1). Yield: 1.62 g (41% of theoretical); C13H17BrFNSi (M=314.269); calc.: molpeak (M+H)+: 314/316 (Br); found: molpeak (M+H)+: 314/316 (Br); HPLC-MS: 7.85 minutes (method B).

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. 156772-60-0, 2,5-Dibromo-3-fluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/234101; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 876919-08-3, 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. 876919-08-3, name is Methyl 3-fluoroisonicotinate, molecular formula is C7H6FNO2, 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 solution ofPreparation 69A (100 mg, 0.42 mmol) in DMA (5 mL) wasadded methyl3-fluoroisonicotinate (65 mg, 0.42 mmol) at rt. The reaction was stirred at170 oc for 1 h in a microwave. The reaction mixture was diluted with water extracted with EtOAc. Organics were washed with brine, dried (Na2 S04), and concentrated. Purification by silica gel chromatography (5:1 PE/EtOAc) gave 50 mg (32%) of the titlecompound as a yellow solid. 1H NMR (300 MHz, CDCh): 8 3.92 (3H, s), 4.27-4.28 (2H,m), 4.81-4.82 (2H, m), 5.78-5.80 (1H, m), 7.00-7.08 (3H, m), 7.65-7.69 (2H, m), 7.97 (1H, d, J = 5.1 Hz), 8.20 (1H, s).

According to the analysis of related databases, 876919-08-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUANTICEL PHARMACEUTICALS, INC.; CHEN, Young, K.; KANOUNI, Toufike; NIE, Zhe; STAFFORD, Jeffrey, Alan; VEAL, James, Marvin; WALLACE, Michael, Brennan; WO2014/100818; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 934-60-1 , The common heterocyclic compound, 934-60-1, name is 6-Methyl-2-pyridinecarboxylic acid, molecular formula is C7H7NO2, 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.

[0349j Methyl 6-methylpicolinate 3.41: To a 250-mL round-bottomed flask was added 6-methylpicolinic acid (TCI, 5.35 g, 39.0 mmol) and MeOH (100 mL). Concentrated sulfuric acid (3.12 mL, 58.5 mmol) was added dropwise. The reaction was heated at reflux for 48 h. After cooling to RT, most of the solvent was evaporated. The resulting residue was diluted with saturated aqueous NaHCO3 and extracted with DCM (2 x 100 mL). The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give 6-methylpicolinate (5.33 g, 35.3 mmol, 90% yield) as a light-yellow oil. MS (M–H) 152.0.

The synthetic route of 934-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); 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. 85148-26-1, name is 3-Chloro-5-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Chloro-5-(trifluoromethyl)pyridine

General procedure: Under an N2 atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol %), dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol) were successively added into a Schlenk tube. The mixture was stirred vigorously at 90 C for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: PE/EA = 15:1) to give the pure products. The reported yields are the average of two runs.

The synthetic route of 85148-26-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Saranya, Gandhi; Viswanathamurthi, Periasamy; Bertani, Roberta; Sgarbossa, Paolo; Malecki, Jan Grzegorz; Journal of Organometallic Chemistry; vol. 831; (2017); p. 1 – 10;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59352-90-8, 5-Bromo-6-methylpyridine-2,3-diamine, 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: C6H8BrN3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

5-Bromo-6-methylpyridine-2,3-diamine (50 mg, 0.25 mmol), 4-chlorophenylboronicacid (45 mg, 0.29 mmol), and cesium carbonate (240 mg, 0.74 mmol) were suspendedin dioxane/water (4:1; v/v) (1.25 ml) and this mixture was degassed (3 x vacuumnitrogen cycles). [1,1 ?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1)dichloromethane complex was added and the mixture degassed again (3 x vacuum30 nitrogen cycles). The resulting reaction mixture was stirred at 110 00 for 16 h. Then, the mixture was allowed to cool and it was worked-up adding chloroform and washing with water and brine. The organic phase was dried and evaporated under reduced pressure to afford a residue of 93 mg. This crude material was purified by flash chromatography (methanol-dichloromethane gradient, 0:100 rising to 10:90) to give 46mg (0.20 mmol, 80percent yield) of the title compound as a solid. Purity 95percent.1H NMR (400 MHz, CHLOROFORM-d) oe ppm 7.35 (d, 2H, J = 8.3 Hz), 7.20 (d, 2H, J =8.3 Hz), 6.78 (s, 1 H), 4.30 (br.s, 2H), 3.23 (br.s, 2H), 2.28 (s, 3H)UPLC/MS (3mm) retention time 1.08 mm.LRMS: m/z 234 (M+1, ixCI).

The synthetic route of 59352-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; CONNOLLY, Stephen; EASTWOOD, Paul Robert; ROBERTS, Richard Spurring; SEVILLA GOMEZ, Sara; CATURLA JAVALOYES, Juan Francisco; (110 pag.)WO2017/64068; (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. 10177-29-4, name is 4-Chloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 10177-29-4

Intermediate4-(2,5-Dichloro-phenoxy)-nicotinic acidTo a suspension of 10 g (63.47 mmol) 4-chloronicotinic acid (commercially available; CAS RN10177-29-4) and 11.38 g (69.81 mmol) 2,5-dichlorophenol (commercially available CAS RN 583-78-8) in 50 mL dry N,N-dimethylformamide were added 17.55 g (126.94 mmol) potassium carbonate, 1.21 g (6.35 mmol) copper(I) iodide and 1.21 g (19.04 mmol) copper nanopowder. The green suspension was stirred at 120 C. (oil bath temperature) for 3 hours and then cooled down to 80 C. At that temperature, 400 mL water were added, the suspension was stirred at 80 C. for 5 min., filtered over Dicalite speed plus (Acros) and the filter cake washed twice with 50 mL water. The resulting filtrate was extracted three times with ethyl acetate and then the pH was adjusted to 4-5 using 140 mL 1M aqueous hydrochloric acid. The resulting green, turbid solution was treated with ethyl acetate, stirred for 5 min. and filtered. The blue solid that had formed was filtered off and the layers of the filtrate were separated. The aqueous layer was saturated with solid sodium chloride and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. To the resulting solid 200 mL saturated aqueous potassium carbonate solution and 200 mL ethyl acetate were added. The aqueous layer was extracted twice with 200 mL ethyl acetate and the pH was adjusted to 4 using 25% aqueous hydrochloric acid. The resulting suspension was extracted three times with ethyl acetate. The combined organic layers were washed three times with water and once with brine, dried over magnesium sulfate, filtered and evaporated to give the desired compound as a light brown solid (7.29 g, 40%). MS (ESI): m/z=281.8 [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, 10177-29-4, 4-Chloronicotinic acid.

Reference:
Patent; Bissantz, Caterina; Dehmlow, Henrietta; Erickson, Shawn David; Kim, Kyungjin; Martin, Rainer E.; Sander, Ulrike Obst; Pietranico-Cole, Sherrie Lynn; Richter, Hans; Ulmer, Christoph; US2011/178089; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem