Category: pyridine-derivatives

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

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

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

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

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

Adding a certain compound to certain chemical reactions, such as: 55934-01-5, 2,4,5-Trichloropyridine, 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, Application In Synthesis of 2,4,5-Trichloropyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2,4,5-Trichloropyridine

To a solution of 2,4,5-trichloropyridine (5 g, 27.4 mmol) in 150 ml of THF was added LDA (2 M in heptane, 20.56 ml, 41.1 mmol) at -78 C. The mixture was stirred at -78 C. for 1 hour. Then methyl formate (8.23 g, 137 mmol) in THF (20 mL) was added quickly into the reaction mixture followed by stirring at -78 C. for 1 hour. The reaction mixture was quenched with aqueous saturated NH4Cl solution and extracted with EtOAc three times. The combined organic layers were dried over anhydrous Na2SO4 and, volatiles were removed under reduced pressure. The residue was purified with silica-gel chromatography (10-100% EtOAc in heptane) to afford the desired compound as a solid (4.2 g, 73%). ESI-MS m/z: 211.8 [M+H]+ (Rt=0.86 min, LC-method 1), 1H NMR (400 MHz, DCM-d2) delta ppm=10.43 (s, 1H), 8.61 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55934-01-5, 2,4,5-Trichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BARBE, Guillaume; BEBERNITZ, Gregory Raymond; GENG, Sicong; GULGEZE EFTHYMIOU, Hatice Belgin; LIAO, Lv; MA, Fupeng; MO, Ruowei; PARKER, David Thomas; PENG, Yunshan; PEUKERT, Stefan; YAMADA, Ken; YASOSHIMA, Kayo; (78 pag.)US2018/111932; (2018); 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 1335210-23-5, name is 1-(2,2-Dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

100 g of compound (2) was charged along with acetonitrile 800 ml followed by acetic acid 100 ml and methane sulphonic acid 5 ml. The contents were heated at 70-80C and maintained for 6-8 hours. The reaction mass was cooled to room temperature and 52 g of compound (4) was added to it followed by addition of potassium carbonate 52.5 g. The reaction mass was stirred for 16-18 hours and 1000 ml of water was added to the reaction mass and then extracted with dichloromethane 1000 ml. The reaction mass was re-extracted two more times with dichloromethane. The combined organic layer was washed with water 500 ml and concentrated to get residue. 300 ml of methanol was charged to the residue and stirred for 30 minutes and then filtered. The residue was washed with methanol 50 ml and then dried and then recrystallized from dichloromethane / methyl tert-butyl ether to get pure compound (5).Yield-70gHPLC Purity: > 99.5 %

With the rapid development of chemical substances, we look forward to future research findings about 1335210-23-5.

Reference:
Patent; CIPLA LIMITED; PHULL, Manjinder Singh; RAO, Dharmaraj Ramachandra; BIRARI, Dilip Ramdas; (28 pag.)WO2018/229798; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 193902-78-2, Adding some certain compound to certain chemical reactions, such as: 193902-78-2, name is tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate,molecular formula is C14H20N4O4, 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 193902-78-2.

Place 4-(5-nitro-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (1.14 g, 3.70 mmol) in 1:1 EtOAc:MeOH (20 mL). Add 10% Pd on carbon using EtOAc (5 mL). Purge the reaction and then add hydrogen. Repeat the purge/fill cycle twice, and place the reaction under a balloon of hydrogen and stir at room temperature for 20 hours. Filter the reaction through a pad of Celite and wash the filter cake with EtOAc. Collect the filtrate and concentrate under reduced pressure to yield 1.01 g (98%) of the title compound. MS(ES): m/z = 279 [M+H].

According to the analysis of related databases, 193902-78-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/53394; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 145325-40-2 ,Some common heterocyclic compound, 145325-40-2, molecular formula is C9H6BrNO2S, 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.

4-Methylene-piperidine-1-carboxylic acid benzyl ester (250 mg, 1.08 mmol) is dissolved in a 0.5 M solution of 9-Bora-bicyclo[3.3.1]nonane in THF (2.16 ml, 1.08 mmol) and heated at 67C for 1.5 hour. The mixture was cooled and Pd C12 dppf (40.8 mg, 0.05 mmol), Cs2CO3 (0.98 g, 3.00 mmol) and a solution 4-Bromo-thieno[2,3-c]pyridine-2- carboxylic acid methyl ester (272 mg, 1.00 mmol) in p=Dioxane (3.0 ml) were added. The mixture was de-gassed and heated at 90C for 3 hours. The mixture was cooled and filtered through silica gel, chasing with EtOAc. The organic layer was concentrated and the residue was further purified by flash chromatography on silica gel using 4 : 1/ CH2CL2 : EtOAc , then 1 : 1/ CH2CL2 : EtOAc as eluant. Product fractions were combined and concentrated to yield 128 mg (30%) of 4-(1-Benzyloxycarbonyl piperidin-4-ylmethyl)-thieno@2,3-cJpyridine- 2-carboxylic acid methyl ester as a yellow solid; RP-HPLC (Table 1, Method M), Rt 2.40 min; m/z: (M + H) + 425.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145325-40-2, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2005/110410; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7379-35-3 ,Some common heterocyclic compound, 7379-35-3, molecular formula is C5H5Cl2N, 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.

A14c. General Method for Substituted Aniline Synthesis via Nucleophilic Aromatic Substitution using a Halopyridine; [] Step 1. Methyl(4-nitrophenyl)-4-pyridylamine: To a suspension of N-methyl-4-nitroaniline (2.0 g, 13.2 mmol) and K2CO3 (7.2 g, 52.2 mmol) in DMPU (30mL) was added 4-chloropyridine hydrochloride (2.36 g, 15.77 mmol). The reaction mixture was heated at 90 °C for 20 h, then cooled to room temperature. The resulting mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL). The organic layer was washed with water (100 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, gradient from 80percent EtOAc /20percent hexanes to 100percent EtOAc) to afford methyl(4-nitrophenyl)-4-pyridylamine (0.42 g)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7379-35-3, its application will become more common.

Reference:
Patent; Bayer Pharmaceuticals Corp.; EP1042305; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem