Day: September 7, 2021

Application of 70298-89-4, 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. 70298-89-4, name is 2,2-Dimethyl-N-pyridin-4-yl-propionamide, molecular formula is C10H14N2O, 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.

N-(Pyridin-4-yl)pivalamide (377 mg, 2.12 mmol) was dissolved in anhydrous tetrahydrofuran under inert atmosphere and cooled to – 78 °C. Within 1 h, a 1.6 M hexane solution of buthyl-lithium (3.3 mL, 5.29 mmol, 2.5eq) was added drop wise. Then the reaction mixture was warmed to 0 °C, stirred for 3 h, and anhydrous dimethylformamide (0.5 mL, 6.35 mmol, 3eq) in anhydrous tetrahydrofuran (3 mL) was added. Subsequently, the solution was warmed to room temperature and stirred for an additional 45 min. The mixture was poured onto a mixture of 6 N HCI (5 mL) and ice (5 g). After stirring for 5 min, the solution was neutralized with K2C03 (3.3 g) and extracted with diethylether. The organic layer was dried over MgS0 and the solvent was removed in vacuo. The residue was purified bycolumnchromatography to get N-(3-formylpyridin-4-yl)pivalamide (258 mg, 59 percent).

According to the analysis of related databases, 70298-89-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13817; (2013); 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. 1427-06-1, name is Methyl 6-fluoropyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. COA of Formula: C7H6FNO2

General procedure: To a 5 mL vial containing a stir bar, 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (50 mg, 0.19 mmol) and 4-fluorobenzonitrile (26 mg, 0.21 mmol) were added Cs2CO3(96 mg, 0.29 mmol) and 0.55 mL DMSO. The resultant mixture was stirred at 80 Celsius for approximately 15 hours. The mixture was cooled to room temperature and then passed through a syringe filter. The filtrate was subjected to FCC to give the title compound (36 mg, 52%). The title compound was prepared using conditions similar to those described in Example 101 using acetonitrile with 10% DMF as the solvent and 6-fluoronicotinic acid methyl ester. MS (ESI): mass calcd. for C21H19FN4O3, 394.14; m/z found, 395.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.77 (dd, J=2.3, 0.5, 1H), 8.46 (s, 1H), 8.31 (dd, J=8.6, 2.3, 1H), 8.08 (d, J=1.3, 1H), 7.83-7.76 (m, 1H), 7.23 (d, J=8.3, 1H), 7.04 (dd, J=8.6, 0.6, 1H), 4.68 (s, 2H), 3.91 (s, 3H), 3.67-3.55 (m, 1H), 2.23-2.07 (m, 4H), 2.00-1.87 (m, 1H), 1.85-1.75 (m, 1H).

The synthetic route of 1427-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (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. 717843-48-6, name is 3-Bromo-6-methylpicolinonitrile, the common compound, a new synthetic route is introduced below. COA of Formula: C7H5BrN2

A solution of 2-(tetaut-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and 3-bromo-6-methylpicolinonitrile (from step 2) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(t?phenyl-phosphine)palladium (5 mol%) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 1000C and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-70% ethyl acetate in hexane to give 3- methylbenzo[f][l,7]naphthyridin-5-amine as a yellow solid. 1H NMR (methanol d-4): delta 8.85 (d, IH), 8.38 (d, IH), 7.72 (d, IH), 7.53-7.61 (m, 2H), 7.34-7.38 (dd, IH), 2.76 (s, 3H). LRMS [M+H] = 210.1

The synthetic route of 717843-48-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; NOVARTIS AG.; WO2009/111337; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 145100-50-1, 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. 145100-50-1, name is 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide. A new synthetic method of this compound is introduced below.

Intermediate 11 (0.15 g, 0.76 mmol) was dissolved in 2.5 mL anhydrousdichloromethane under N2. 0.21 mL (1.22 mmol) of N,NDiisopropylethylaminewas added and stirred for 15 min at roomtemperature. The reaction was cooled to 0 C and 0.33 g (0.91 mmol) 2-pyridyltriflimide was added and the reaction stirred overnight at roomtemperature. At completion extraction was done with dichloromethane(3 × 10 mL) and the organic fractions washed with saturated aqueoussodium chloride before being dried over sodium sulfate and concentratedin vacuo. Purification was done by flash chromatography 95:5(DCM:MeOH) to yield 0.06 g (25%) of the product as a light red oil. TLCeluents used (9:1 Dichloromethane: MeOH). 1H NMR (500 MHz;CDCl3): delta 7.18 (t, J = 7.9 Hz, 1H), 7.12 (d, J = 7.5 Hz, 1H), 7.07 (d,J = 8.0 Hz, 1H), 3.10-3.01 (m, 2H), 2.84 (dd, J = 16.0, 10.6 Hz, 1H),2.77-2.71 (m, 2H), 2.44 (s, 6H), 2.23-2.18 (m, 1H), 1.67-1.62 (m, 1H).13C NMR (400 MHz, CDCl3): delta 148.23, 139.75, 129.72, 129.54, 127.07,123.54, 120.35, 118.54, 117.17, 113.97, 59.95, 41.94, 32.51, 25.20,23.62. Calcd C13H17NO3SF3 for [M + H]+: 324.0881. Found:324.0083.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,145100-50-1, 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide, and friends who are interested can also refer to it.

Reference:
Article; Perry, Charles K.; Casey, Austen B.; Felsing, Daniel E.; Vemula, Rajender; Zaka, Mehreen; Herrington, Noah B.; Cui, Meng; Kellogg, Glen E.; Canal, Clinton E.; Booth, Raymond G.; Bioorganic and Medicinal Chemistry; vol. 28; 3; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 886373-00-8, Adding some certain compound to certain chemical reactions, such as: 886373-00-8, name is 5-Bromo-2-ethoxypyridin-3-amine,molecular formula is C7H9BrN2O, 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 886373-00-8.

Intermediate 61 lambda/-[5-Bromo-2-(ethyloxy)-3-pyridinyl]benzenesulfonamide A solution of 5-bromo-2-(ethyloxy)-3-pyridinamine (1.45 g) in anhydrous pyridine (15 ml) was treated with benzenesulfonyl chloride (1.03 ml) then stirred at RT for 20 hr. The reaction was evaporated to dryness and the residue was purified by column chromatography on silica, eluting with 30% hexanes in DCM, to give the title compound (1.86 g).1H NMR: deltaH (DMSOd6, 400 MHz) 10.09 (1 H, s), 8.03 (1 H, d), 7.74 (1 H, d), 7.71 (1 H, d), 7.64 (1 H, d), 7.57 (2H, d), 4.05 (2H, q), 1.07 (3H, t).

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. 886373-00-8, 5-Bromo-2-ethoxypyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147187; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 186593-42-0, 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. 186593-42-0, name is 3-Bromo-2-methyl-5-nitropyridine. A new synthetic method of this compound is introduced below.

4-(2-Methyl-5-nitropyridin-3-yl)-N-neopentyIbenzenesulfonamide. The compound obtained above (30 mg, 0.085 mmol), 3-bromo-5-nitro-2-methylpyridine (1.0 eq., 18 mg), K2CO3 (3 eq., 35 mg) and Pd(PPh3)4 (10 mol %, 10 mg) were dissolved in 3 ml DMErEtOH (9: 1). The solution was stirred at 800C for 24 hr under nitrogen. The mixture was concentrated in vacuo. Column chromatography (SiOa; 3:1 Hex: EtOAc) yielded 20 mg of the target compound. (CaIc. mass: 364, obs. mass 364).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,186593-42-0, 3-Bromo-2-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; KEMIA, INC.; WO2008/21388; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59237-53-5 , The common heterocyclic compound, 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, 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.

[0202] A solution of methyl 6~chloro-5-nitronicotinate (5 g, 23.09 mmol), 4~(2,,4~ difluorophenoxy)piperidine hydrochloride (6.92 g, 27.7 mmol) and K2CO3 (9.57 g, 69.3 mmol) in ACN (57.7 mL) was stirred at 80°C for 5 hours. The reaction mixture was poured into water and extracted with EtOAc (3 x 250 mL). The organic layers were combined, dried over NazSC and filtered. The filtrate was concentrated in vacuo and purified by column chromatography (ISCO column) elutmg with a gradient of 0-100percent EtOAc in heptane, to give the title compound as a yellow solid (6.04 g, 66.5percent). lR NMR (500 MHz, DMSO-afe) delta ppm 1.74 (dq,./ 12. KK. 4.17 Hz, 2 I .}. 2.04 (ddd, J=9.76, 6.83, 3,42 Hz, 2 H), 3.45 (td, 7=8.91, 4.15 Hz, 2 H), 3.71 – 3.76 (m, 2 H), 3.85 (s, 3 H), 4,66 (tt, J=7.51, 3,72 Hz, 1H), 7.00 – 7,06 (m, 1H), 7.27 – 7.36 (m, 2 H), 8.56 (d,/ 1.46 Hz, 1H), 8.82 (d,,/ 1.46 Hz, 1H); ESI-MS m/z | M I I . 394.2.

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (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. 7584-05-6, name is 3-Methylisonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6N2

Preparation of (E)-3-(2-(dimethylamino)vinyl)isonicotinonitrile; [00150] To a solution of 3-methylisonicotinonitrile (10 g, 85 mmol) in DMF (100 mL) was added l,l-dimethoxy-N,N-dimethylmethanamine (18.05 mL, 135 mmol). The mixture was heated to reflux overnight. The mixture was cooled to rt and an additional 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine was added to the mixture, and it was again heated to reflux. After heating the mixture overnight, it was cooled to rt and an additional 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine was added to the mixture. The mixture was heated overnight at reflux. The mixture was cooled to rt and an additional 3.0 mL of 1 , 1 -dimethoxy-N,N- dimethylmethanamine were added. The mixture was again heated to reflux. After heating the mixture overnight, it was cooled to rt. To the mixture was added 3.0 mL of l,l-dimethoxy-N,N-dimethylmethanamine. The mixture was heated to reflux overnight. The mixture was cooled to rt and was concentrated under reduced pressure. The residue was dissolved in dichloromethane and was loaded onto a BIOTAGE 65 + M cartridge and was purified using a 10-70% EtOAc in hexanes gradient. The expected product, (E)-3-(2-(dimethylamino)vinyl)isonicotinonitrile (7.97 g, 46.0 mmol, 54.4 % yield), was isolated as a bright-yellow solid. LC/MS: m/z 174.11 (M+H)+ , 1.690 min (method 1). 1H NMR (500 MHz, chloroform-^) I ppm 1H NMR (500 MHz, chloroform-^ I ppm 8.69 (s, 1 H) 8.14 (d, J= 5.19 Hz, 1 H) 7.23 (d, J= 4.88 Hz, 1 H) 7.15 (d, J= 13.43 Hz, 1 H) 5.21 (d, J= 13.73 Hz, 1 H) 2.95 (s, 6 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, 7584-05-6, 3-Methylisonicotinonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/158396; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-84-1, 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. 128071-84-1, name is 4-Bromo-2-chloropyridine-3-carboxaldehyde. A new synthetic method of this compound is introduced below.

Example 104b 2-Chloro-4-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)nicotinaldehyde 104b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 104a (1.1 g, 5.0 mmol), 3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 101e (477 mg, 2.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (230 mg, 0.25 mmol), XantPhos (430 mg, 0.75 mmol), Cs2CO3 (1.6 g, 5.0 mmol), and 1,4-dioxane (50 mL). After three cycles of vacuum/argon flush, the mixture was heated at 65C for 2 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (40:1) to afford 104b as a yellow solid (1.1 g, 80%). MS: [M+H]+ 330.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-84-1, its application will become more common.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13143-47-0, 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.13143-47-0, name is 1-(4-Aminophenyl)-1H-pyridin-2-one, molecular formula is C11H10N2O, molecular weight is 186.21, as common compound, the synthetic route is as follows.

General procedure: To a stirred solution of 1-(4-aminophenyl)pyridin-2(1H)-one (3a) (0.90 g, 4.8 mmol), K2CO3 (0.80 g, 5.8 mmol) and DMAP (0.05 g, 0.4 mmol) inTHF (20 mL), solution of 2-nitrobenzoyl chloride (2a) (1.15 g, 6.24 mmol) in THF (5 mL) was addedat room temperature and the mixture was refluxed for 2 h. The reaction mixture was cooled downto room temperature and concentrated under reduced pressure. Then water (100 mL) was addedto the mixture and stirred for 10 min at room temperature. The resulting precipitate was collectedby filtration. The reaction was monitored by TLC with EA.

The chemical industry reduces the impact on the environment during synthesis 13143-47-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Wenzhi; Yuan, Jing; Fu, Xiaoli; Meng, Fancui; Zhang, Shijun; Xu, Weiren; Xu, Yongnan; Huang, Changjiang; Molecules; vol. 21; 4; (2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem