Day: August 12, 2021

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. 94166-64-0, name is 2-Chloro-6-nitropyridine, the common compound, a new synthetic route is introduced below. Formula: C5H3ClN2O2

Preparation of N-(3-(4-(6-Nitropyridin-2-yl)piperazin-l- yl)propyl)cyclohexanecarboxamideN-(3-(Piperazin-l-yl)propyl)cyclohexanecarboxamide (128 mg, 0.50 mmol), and 2- chloro-6-nitropyridine (79 mg, 0.50 mmol) were dissolved in dry acetonitrile (8 ml) in a 10 mL microwave tube and diisopropylethylamine (87 muL·, 0.50 mmol) added. The mixture was stirred and then heated in the microwave oven at 120C for 60 min. TLC (5% MeOH-EtOAc) showed the presence of 2 close running products of Rf 0.16 and 0.10. The reaction mixture was evaporated under reduced pressure to give a brown residue that was purified by chromatography on silica gel eluting with a 0-10% methanol in ethyl acetate gradient. The product was further purified by semi-preparative HPLC using a gradient of 50-95% methanol in water over 20 min (at) 18 ml/min (Gemini C18, 11 OA, 150 x 21.2 mm, 5 muiotaeta; Rt 10.8 min) to give the product (37 mg, 19%).LCMS: calcd for C19H29N5O3, 375.2; found 376.1 [M+H] . and 13C NMR were consistent with the structure.Purity was 96% by HPLC (UV 254nm).

The synthetic route of 94166-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GE HEALTHCARE LIMITED; MEDI-PHYSICS, INC.; NEWINGTON, Ian, Martin; WYNN, Duncan George; NAIRNE, Robert James Domett; GUILBERT, Benedicte; MANDAL, Subrata; JINTO, Jose; VARADARAJAN, Sunderaraman; RANGASWAMY, Chitralekha; BETTS, Helen; DAVIS, Rebecca; WO2011/150183; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 100-54-9 , The common heterocyclic compound, 100-54-9, name is Nicotinonitrile, molecular formula is C6H4N2, 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.

General procedure: A solution of the appropriate cyanophenyl 1a-1j (0.1mol), hydroxylamine hydrochloride (0.2 mol), and TEA (0.2 mol) in methanol was stirred at room temperature for 1 h, then heated under reflux until the disappearance of the starting materials (TLC analysis). After cooling, the solvent was evaporated to dryness under reduced pressure to give the crude, which was dissolved in ethyl acetate (400 mL) and washed with brine (3×100 mL) and dried with Na2SO4. Ethyl acetate was evaporated under reduced pressure to yield the compounds 2a-2j.

The synthetic route of 100-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cai, Jin; Wei, Hongtao; Hong, Kwon Ho; Wu, Xiaoqing; Cao, Meng; Zong, Xi; Li, Lushen; Sun, Chunlong; Chen, Junqing; Ji, Min; European Journal of Medicinal Chemistry; vol. 96; (2015); p. 1 – 13;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 68325-15-5, 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 68325-15-5, name is 3-Chloro-4-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To an ice-cooled solution of 2-methyl-2-(morpholin-4-yl)propan-1 -ol (4.00 g, 25.1 mmol) in THF (12.5 ml) under an argon atmosphere was added NaH 60% dispersion on mineral oil (1 .1 g, 27.4 mmol) slowly portionwise. The reaction mixture was stirred with ice-cooling for 1 h and a solution of 3-chloropyridine-4-carbonitrile (4.10 g, 29.6 mmol) in THF (64.5 ml) was added. The reaction was allowed to warm slowly to RT and stirred at this temperature for 16h. The reaction was then heated under reflux conditions for 2h. The reaction mixture was quenched with a sat. NH4CI solution and extracted with EtOAc. The organics were combined and washed with sat. NaCI, filtered through a hydrophobic filter and concentrated. The residue was crystallized with MTBE and collected by filtration to give the title compound (2 g, 35% yield) which was used without further purification.1H-NMR (400MHz, DMSO-d6): delta [ppm]= 8.75 (s, 1 H), 8.38 (d, 1 H), 7.78 (d, 1 H), 4.19 (s, 2H), 3.44 – 3.52 (m, 4H), 2.57 – 2.62 (m, 4H), 1.10 – 1 .23 (m, 6H).

According to the analysis of related databases, 68325-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA FARBER CANCER INSTITUTE; SIEGEL, Stephan; SIEGEL, Franziska; SCHULZE, Volker; BERGER, Markus; GRAHAM, Keith; KLAR, Ulrich; KNUT, Eis; SUeLZLE, Detlev; BOeMER, Ulf; KORR, Daniel; PETERSEN, Kirstin; MOeNNING, Ursula; EBERSPAeCHER, Uwe; MOOSMAYER, Dieter; MEYERSON, Matthew; GREULICH, Heidi; KAPLAN, Bethany; HARB, Hassan, Youssef; DINH, Phi, Manh; (324 pag.)WO2019/81486; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1187236-18-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1187236-18-5 as follows.

Under the protection of -78 C and N2,To ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate (3.50 g, 13.0 mmol)Add in anhydrous DCM (80 mL) suspensionDiisobutylaluminum hydride (18.50 mL, 18.50 mmol, 1.0 M).The mixture was stirred at -78 C overnight.After the reaction is over, move to 0 C.And add water (0.75mL) in turn.15% NaOH aqueous solution (0.75mL)The reaction was quenched with water (2 mL).The resulting mixture was stirred at room temperature for 15 minutes.Then add Et2O (50 mL),EtOAc (50 mL) and Mg 2 SO 4 (20 g).Continue stirring for 15 minutes and filter again.The resulting filter cake was rinsed with EtOAc (200 mL).The filtrate was concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (EtOAc /EtOAcTo give the title compound as a pale yellow solid (1.50g, 51% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1187236-18-5, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
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 128071-75-0, name is 2-Bromonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 128071-75-0

Wittig Reaction (8) (0263) Ethyl (triphenylphosphoranylidene) acetate (2.80 g, 8.17 mmol) was added to a solution of 2-bromonicotinaldehyde (1.0 g, 5.4 mmol) in dry DCM (dichloromethane) at 0 C. and stirred for 8 h at room temperature. The solvent was then evaporated under vacuum. The colorless oil was partitioned between ethylacetate and water. The organic layer was washed with water, brine and dried over Na2SO4. It was then filtered and evaporated to give an oil from which the title compound 8 was isolated by column chromatography (Si-gel, PE: EA=15:1). Yield: 1.3 g, 94%; State:colorless oil.

With the rapid development of chemical substances, we look forward to future research findings about 128071-75-0.

Reference:
Patent; The Florida State University Research Foundation, Inc.; Alabugin, Igor V.; Mondal, Sayantan; Mohamed, Rana K.; (60 pag.)US2016/347778; (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. 696-54-8, name is Pyridine-4-aldoxime, the common compound, a new synthetic route is introduced below. Formula: C6H6N2O

General procedure: To a mixture of oxime (0.86mmol) and Raney Co 2724 (200 mg, slurry in H2O) were addedTHF (1.5 mL) and MeOH (1.5 mL). The reaction mixture waspurged with nitrogen twice then pressurized to 60 psi H2 at 50C. The reaction was deemed complete when H2 consumptionceased, typically after 2-10 h. Upon completion, the reactionwas filtered through a pad of celite and washed with MeOH. Thefiltrate was then concentrated under reduced pressure, andpurified by flash chromatography (CH2Cl2-MeOH, 95:5) tofurnish the title compound. Alternatively, the product was convenientlyisolated in high purity as the HCl salt. After filteringoff the catalyst, the filtrate solvent was changed to MTBE (1.5mL) and HCl (0.95 mmol, 1 M in Et2O) was added dropwise tocrystallize the salt. The resulting HCl amine salt was then isolatedby filtration and washed with MTBE.

The synthetic route of 696-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baucom, Kyle D.; Guram, Anil S.; Borths, Christopher J.; Synlett; vol. 26; 2; (2015); p. 201 – 204;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13535-01-8, 5-Bromopyridin-3-amine, 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, 13535-01-8, blongs to pyridine-derivatives compound. Recommanded Product: 13535-01-8

To a solution of 5-bromopyridin-3-amine (4.75 g, 27.45 minol) in dioxane (45 mL) was added cyclopropylboronic acid (4.75 g, 55.30 minol), C52CO3(28 g, 85.67 minol), tetrakis(triphenylphosphane) palladium(1.66 g, 1.44 minol) and water (5 mL) at room temperature. The resultingminxture was then stirred for 15 h at 100 C. After cooling to room temperature, the reaction mxiture was diluted with water (200 mL). The resultingminxture was extracted with ethyl acetate (500 mL x 3). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 100% gradient) to yield 5-cyclopropylpyridin-3-amine as light brown oil (2.08 g, 56%). MS: m/z = 135.0 [M+Hj .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13535-01-8, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; SHERER, Brian A.; BRUGGER, Nadia; (546 pag.)WO2017/106607; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59718-84-2, 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.59718-84-2, name is Methyl 3-methylpicolinate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.

5 g quantity of methyl 3- [2- (3-benzyloxy-4-methoxy phenyl) oxazol-4-yl] propionate obtained in Reference Example 48 and 3.2 g of methyl 3-methylpicolinate were dissolved in 150 ml of dimethoxyethane. While stirring the solution with ice cooling 1.2 g of sodium hydride was added thereto and further stirred. The reaction mixture was heated and refluxed for 4 hours. At the completion of the reaction, a saturated aqueous ammonium chloride solution was added to the mixture while stirring with ice cooling, and the mixture was further stirred. After stirring the reaction mixture for 30 minutes, water was added thereto and ethyl acetate extraction was performed. The organic layer was washed twice with water, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n- hexane: ethyl acetate = 2:1), thereby yielding 5.5 g of colorless oily substance methyl 2- [2- (3-benzyloxy-4-methoxyphenyl) oxazol-4- ylmethyl] -3- (3-methylpyridin-2-yl) -3-oxopropionate. 1H-NMR (CDCl3) delta: 8.49 (IH, dd, J = 4.8, 1.2 Hz), 7.59-7.28 (1OH, m), 6.91 (IH, d, J = 9.0 Hz), 5.23-5.16 (3H, m) , 3.91 (3H, s) , 3.65 (3H, s), 3.37-3.18 (2H,m,) 2.59 (3H, s)

Statistics shows that 59718-84-2 is playing an increasingly important role. we look forward to future research findings about Methyl 3-methylpicolinate.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2007/58338; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58584-86-4 , The common heterocyclic compound, 58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, 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 mixture of 3-(dispiro[2.0.2. l]heptan-7-ylmethoxy)-lH-pyrazole (0.94 g, 4.9 mmol), ethyl 2,6-dichloropyridine-3-carboxylate (1.15 g, 5.23 mmol), potassium carbonate (0.83 g, 6.0 mmol), and l,4-diazabicyclo[2.2.2]octane (0.12 g, 1.1 mmol) in DMSO (16 mL) was stirred for 24 hours. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine and water, dried over sodium sulfate, and evaporated under vacuum. The residue was purified by silica gel column chromatography eluting with 0-20% ethyl acetate in hexanes to give ethyl 2-chloro-6-(3-(dispiro[2.0.2.1]heptan-7-ylmethoxy)-lH-pyrazol-l-yl)nicotinate (1.39 g, 75% yield) as a colorless solid. ESI-MS m/z calc. 373.11932, found 374.2 (M+l)+; Retention time: 0.87 minutes. *H NMR (400 MHz, Chloroform-d) delta 8.36 (d, J = 2.8 Hz, 1H), 8.27 (d, J = 8.5 Hz, 1H), 7.72 (d, J = 8.5 Hz, 1H), 5.96 (d, J = 2.9 Hz, 1H), 4.41 (q, J = 7.1 Hz, 2H), 4.30 (d, J = 7.0 Hz, 2H), 1.94 (t, J = 7.0 Hz, 1H), 1.42 (t, J = 7.1 Hz, 3H), 1.02-0.89 (m, 4H), 0.75-0.65 (m, 2H), 0.65-0.53 (m, 2H)

The synthetic route of 58584-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ALCACIO, Timothy; BAEK, Minson; GROOTENHUIS, Peter; HADIDA RUAH, Sara, Sabina; HUGHES, Robert, M.; KESHAVARZ-SHOKRI, Ali; MCAULEY-AOKI, Rachel; MCCARTNEY, Jason; MILLER, Mark, Thomas; VAN GOOR, Fredrick; ZHANG, Beili; ANDRESON, Corey; CLEVELAND, Thomas; FRIEMAN, Bryan, A.; KHATUYA, Haripada; JOSHI, Pramod, Virupax; KRENITSKY, Paul, John; MELILLO, Vito; PIERRE, Fabrice, Jean Denis; TERMIN, Andreas, P.; UY, Johnny; ZHOU, Jinglan; ABELA, Alexander, Russell; BUSCH, Brett, Bradley; PARASELLI, Prasuna; SIESEL, David, Andrew; (329 pag.)WO2018/64632; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 40296-46-6 ,Some common heterocyclic compound, 40296-46-6, molecular formula is C8H7Cl2NO2, 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.

Sodium hydroxide (40 mL, 6.25 M solution) was added to a stirred solution of 4,6-dichloronicotinic acid ethyl ester (22) (25.95 g, 118 mmol) in 4:1:1 THF:MeOH:water (600 mL). After 30 minutes, the reaction mixture was acidified to pH 2 with concentrated HCl, diluted with 1:1 EtOAc:Et2O and washed with water and brine. The organic layer was dried (Na2SO4) and concentrated. The resulting off-white solid was twice concentrated from toluene to give the desired product (23) as a white solid (21.73 g, 96%).

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. 40296-46-6, Ethyl 4,6-dichloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wallace, Eli; Hurley, Brian; Yang, Hon Woon; Lyssikatos, Joseph; Blake, Jim; US2005/49419; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem