Tag: M.W:200-300

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. 777931-67-6, name is 3-Bromo-2-chloro-6-methoxypyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

Into a 100-mL vial maintained with an inert atmosphere of nitrogen, to a solution of 3-bromo-2-chloro-6-methoxypyridine (2.00 g, 8.900 mmol, 1.00 equiv.) in 1,4-dioxane (20 mL), added Pd(dppf)Cl2.CH2Cl2 (0.36 g, 0.450 mmol, 0.05 equiv.), Zn(CH3)2 (17 mL, 17.000 mmol, 2.00 equiv.). The resulting solution was stirred 16 h at 90 C. The mixture was concentrated under vacuum. The residue product was purified by chromatogram on silica gel with ethyl acetate/petroleum ether (2:98) to yield 2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylbutanal as yellow oil. Mass spectrum (ESI, m/z): Calculated for C7H8ClNO, 158.0 [M+H], found 157.8.

The synthetic route of 777931-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (179 pag.)US2019/47959; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89364-04-5 ,Some common heterocyclic compound, 89364-04-5, molecular formula is C5H3BrN2O2, 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.

Step 1: 3-(4-bromophenyl)-4-nitropyridine To a stirred solution of 3-bromo-4-nitropyridine (100 g, 492.6 mmol), (4-bromophenyl)boronic acid (98.6 g, 492.6 mmol), and potassium carbonate (203.9 g, 1.47 mol) in toluene (1000 ml)-water (100 ml) was added tetrakis(triphenylphosphine)palladium (14.8 g, 12.8 mmol) at room temperature under nitrogen atmosphere; the mixture was degassed with nitrogen three times. The resulting mixture was stirred at 50 C. overnight. TLC showed the reaction was complete. The solid was removed through filtration and washed with ethyl acetate (100 ml*3). The organic layer was collected and the aqueous layer was extracted with ethyl acetate (100 ml*2). The combined organic layers were washed with brine (400 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel pad (eluted with 10-33% ethyl acetate in hexane) to afford 3-(4-bromophenyl)-4-nitropyridine (89 g, yield 65%) as yellow solid.

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. 89364-04-5, 3-Bromo-4-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74695-44-6, 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. 74695-44-6, name is 5,7-Dichlorothieno[3,2-b]pyridine, molecular formula is C7H3Cl2NS, 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.

(1) A mixture of 5,7-dichlorotheno[3,2-b]pyridine (0.52 g), triethylamine (0.90 mL), 4-(methylsulfonyl)piperidine mono hydrochloride (0.62 g), and ethylene glycol (1.1 mL) was stirred at 120C for 6 h. Ethylene glycol (4.0 mL) and 1,4-dioxane (4.0 mL) were added, and the mixture was further stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried with anhydrous magnesium sulfate, and then silica gel was added to the organic layer. Silica gel and the desiccant were removed by filtration, the filtrate was concentrated under reduced pressure, and the resulting solids were washed with a mixture solution of ethyl acetate and diisopropyl ether. The resulting solids were purified by silica gel column chromatography (ethyl acetate/hexane = 1:1-1:0) to obtain 5-chloro-7-(4-(methylsulfonyl)piperidin-1-yl)thieno[3,2-b]pyridine (0.11 g).

According to the analysis of related databases, 74695-44-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2003131; (2008); A1;,
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. 17117-13-4, name is 2-Bromo-4-ethoxypyridine. A new synthetic method of this compound is introduced below., Formula: C7H8BrNO

Under an argon atmosphere, 0.81 g (4.00 mmol) of 2-bromo-4-ethoxy-pyridine, 1.02 g (6.40 mmol) of 2,6-difluoro-pyridyl-3-boronic acid, 0.0374 g (0.032 mmol) of Pd(PPh3)4 were dissolved in 30 mL of dioxane, followed by addition of 10 mL of an aqueous solution of 5wt% K2CO3, heated to reflux, stirred for 18 h. After naturally cooled to room temperature, an appropriate amount of distilled water was added, and the solution was extracted several times with ethyl acetate, the organic phase were combined and dried over anhydrous MgSO4. After filtration, solvent was removed from the filtrate under reduced pressure to give the crude product. The crude product was purified to silica gel column chromatography using a mixture of ethyl acetate and n-hexane (v/v=1:4) as eluent to obtain 0.56g of a colorless solid product in 59.6% yield. 1H NMR (400 MHz, CDCl3, ppm): delta 8.92 (d, 1H), 8.65 (d, 1H), 7.75 (d, 1H), 7.43 d, 1H), 6.92 (s, 1H), 4.12 (m, 2H), 1.90 (m, 3H).

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, 17117-13-4, 2-Bromo-4-ethoxypyridine.

Reference:
Patent; Ocean’s King Lighting Science & Technology Co., Ltd.; ZHOU, Mingjie; WANG, Ping; ZHANG, Juanjuan; ZHANG, Zhenhua; EP2727928; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1060814-36-9 ,Some common heterocyclic compound, 1060814-36-9, molecular formula is C15H21NO5, 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.

Step C: Ethyl 4,5,6,7-tetrahydrofuro[3,2-c]pyridine-2-carboxylateTo a solution of 5-tert-Butyl 2-ethyl 6,7-dihydrofuro[3,2-c]pyridine-2,5(4H)- dicarboxylate (0.5g, 1.7 mmol) in DCM was added trifluoroacetic acid (TFA) (0.13 mL, 1.7 mmol) at 0-5 C. After the completion of addition, the reaction mixture was allowed to stir for 6 hours. The excess solvent and reagents were evaporated under reduced pressure. The crude product was triturated with hexane to afford the title compound as TFA salt (0.5 g, Yield 95 %). 1H NMR (DMSO-d6) 5(ppm): 1.36 (3Eta, t, – CH3), 2.77 (2H, brs, -CH2), 3.74 (2H, brs, -CH2), 4.32-4.38 (4H, m, -CH2), 5.02 (1H, brs, -NH), 7.02 (1H, s, Ar-H); MS m/z: 196.1 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060814-36-9, its application will become more common.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LTD; RAJAGOPAL, Sridharan; KILAMBI, Narasimhan; KACHHADIA, Virendra; RATHINASAMY, Suresh; BALASUBRAMANIAN, Gopalan; MANI, Umamaheswari; RAJAGOPALAN, Nirmala; PUSHPARAJ, Judy Auxcilia; ROY, Anshu Mittal; VISHWAKARMA, Lolaknath Santosh; NARAYANAN, Shridhar; KALIYAMOORTHY, Vadivel; THANASEKARAN, Ponpandian; THATAVARTHY KRISHNA, Rama; KANNAN, Kalaivani; KULATHINGAL, Jayanarayan; MOOKKAN, Jeyamurugan; CHIDAMBARAM VENKATESWARAN, Srinivasan; AHAMED ALI, Fakrudeen; WO2012/117421; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54232-43-8, 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. 54232-43-8, name is 6-Bromo-5-methoxypicolinic acid, molecular formula is C7H6BrNO3, 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.

A mixture of 6-bromo-5-methoxy-pyridine-2-carboxylic acid (0.3 g, 1 mmol), 3- chlorophenylboronic acid (CAN 63503-60-6, 0.23 g, 1 mmol), tris(dibenzylideneacetone)- dipalladium(0) (CAN 52409-22-0, 0.12 g), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (CAN 161265-03-8, 0.15 g) and potassium carbonate (0.21 g, 2 mmol) in 1,4-dioxane (10 mL) was stirred for 12 h at 110C under a nitrogen atmosphere. The reaction mixture was filtered, concentrated under reduced pressure and purified by column chromatography (silica gel, 10 g, eluting with 10% methanol in methylene chloride) to give the title compound (0.1 g, 29%); MS (EI): m/e = 264.0[M+H]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 54232-43-8, 6-Bromo-5-methoxypicolinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7477-10-3 , The common heterocyclic compound, 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, molecular formula is C6H3ClN2O4, 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 compound 4 and different primary and secondary amines were stirred at rt for 1h, followed by extraction with EtOAc. The extract was then washed with 1N HCl, water, and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography (hexane/EtOAc=2:1) to give product 6 as a solid. 4.2.4.3 6-(Benzylethylamino)-5-nitronicotinic acid (6c) Procedure A was used with compound 5 (405 mg, 2.0 mmol) and benzyl-ethyl-amine (540 mg, 4.0 mmol) to afford product 6c as a yellow solid (428 mg, 71%). 1H NMR (300 MHz, CDCl3) delta: 8.93 (s, 1H), 8.65 (s, 1H), 7.32-7.21 (m, 5H), 4.85 (s, 2H), 3.48 (q, J = 6.9 Hz, 2H), 1.22 (t, J = 6.9 Hz, 3H). ESI-MS: m/z (300, MH-).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate, molecular formula is C8H5ClF3NO2, molecular weight is 239.58, as common compound, the synthetic route is as follows.Formula: C8H5ClF3NO2

Sodium hydride (1.1 g, 31.4 mmol) was added in portions to cyclopropylmethanol (20 mL) and the mixture was stirred at room temperature for 0.5 hours. 6-Chloro-5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (1.5 g, 6.3 mmol) was added and the resulting solution was stirred at 80 C. for 1 h. Water (20 mL) was added; the solution was acidified with 6 N hydrochloric acid and then concentrated to give a residue which was partitioned between water (30 mL) and ethyl acetate (20 mL). The aqueous solution was extracted with ethyl acetate (2×20 mL) and the combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude target compound. The crude target compound was purified by column chromatography (silica gel, 10 g, 15% ethyl acetate in petroleum ether) to give the title compound (1.4 g, 85%) as white solid; MS (EI): m/e=262.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211518-35-2, Methyl 6-chloro-5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; Bissantz, Caterina; Grether, Uwe; Hebeisen, Paul; Kimbara, Atsushi; Liu, Qingping; Nettekoven, Matthias; Prunotto, Marco; Roever, Stephan; Rogers-Evans, Mark; Schulz-Gasch, Tanja; Ullmer, Christoph; Wang, Zhiwei; Yang, Wulun; US2012/316147; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 86847-84-9 , The common heterocyclic compound, 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide, molecular formula is C10H13ClN2O, 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 solution of 2-chloro-6pivaloylaminopyridine (10.5 g, 49.528 mmol) in THF (150 mL) is prepared under N2 and cooled to -80 0C. t-BuLi IM in pentane (108.962 mmol, 2.2 equiv.) is added carefully via an addition funnel under rigorously anhydrous conditions, over 1 hour. Once the addition is complete, the mixture is kept at -8O0C for 3 hours, at which point a solution of iodine (15.1 g, 59.431 mmol, 1.2 equiv.) in 50 mL THF under N2, is added slowly in one portion. After the addition, the cooling bath is removed and the reaction mixture allowed to warm up to room temperature under stirring for 2 hours. Finally the reaction mixture is quenched by slowly adding 50 mL of IM HCl. The mixture is then concentrated under vacuum to remove part of the THF, and the residue is partitioned between EtOAc and water. A 10% sodium thiosulfate solution is added until no further decolourisation occurred and that 2 clear phases are visible. The aqueous layer is extracted with EtOAc, the organic layers are gathered, washed with brine, dried over Na2Stheta4, and solvent is removed to afford an oil titrating 65 % of the desired material. This crude is refluxed in 100 mL of IM HCl and is refluxed for 5 hours at which point the depivaloylated product is completely formed. The pH is adjusted to 12 by slow addition OfNaHCO3 and extracted with DCM. The organic layer is concentrated and columned using 7/3 DCM/Cyclohexane as the eluent (Rf 9/21) to afford the title compound as an oil which solidified on standing

The synthetic route of 86847-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; WO2008/65199; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 380380-64-3, 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. 380380-64-3, name is 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, molecular formula is C7H6BrN5, 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.

Under the protection of nitrogen, add 17.7g of 2-methyl-5- (5-bromopyridin-2-yl) tetrazole, 27.7g of borate intermediate, 0.663g of tricyclohexylphosphine and 0.23L of dioxane Stir to dissolve; add a solution of potassium carbonate 175g in water 70mL at one time; add 0.88g of tris (dibenzylideneacetone) dipalladium, vacuum-nitrogen replacement three times, then heat the reaction to 70C, and keep the reaction for 1 hour, filter the reaction Liquid, rinse, add 15% saline solution to the mother liquor (the mass concentration refers to the mass of sodium chloride as a percentage of the total mass of saline solution) 100mL, separate layers, separate organic phase, and concentrate in vacuum (temperature 45 65 , pressure -0.08MPa -0.1MPa) to dry, the crude product is stirred in ethyl acetate 120mL) for 12 hours to 16 hours and filtered, and the wet product is dried in a vacuum (pressure -0.01MPa -0.1MPa) oven Dry at 45 C to 55 C for 8 hours to 12 hours to obtain 26.0 g of off-white solid as terdazolamide phosphate II, with a total yield of 55.1% (based on benzyl 3-fluoro-4-bromophenylcarbamate) ). HPLC purity 96.23%.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 380380-64-3, 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine.

Reference:
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Chen Jian; Liu Zhenfeng; Ying Shuhuan; (16 pag.)CN110804038; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem