Pyridine-derivatives

Application of 65001-21-0 ,Some common heterocyclic compound, 65001-21-0, molecular formula is C5H3BrClNO2S, 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.

Example 36A tert-Butyl 4-{[(5-bromopyridin-3-yl) sulphonyl]amino}piperidine-1-carboxylate 5-Bromopyridine-3-sulphonyl chloride (1 g, 3.9 mmol) was dissolved in dichloromethane (20 ml), the mixture was cooled to 0 C. and tert-butyl 4-aminopiperidine-1-carboxylate (1.18 g, 5.8 mmol) and N,N-diisopropylethylamine (1.7 ml, 9.7 mmol) were added. The reaction mixture was stirred at RT overnight and concentrated, and the residue was purified chromatographically by HPLC (Method 9). This gave 1.0 g (62% of theory) of the title compound. 1H NMR (300 MHz, DMSO-d6): delta=ppm 1.09-1.24 (m, 2H), 1.33 (s, 9H), 1.47-1.59 (m, 2H), 2.66-2.83 (m, 2H), 3.19-3.25 (m, 1H), 3.63-3.75 (m, 2H), 8.09 (br. s, 1H), 8.36 (t, 1H), 8.91 (d, 1H), 8.95 (d, 1H). LC-MS (Method 4): Rt=1.19 min; MS (ESIneg): m/z=420.3 [M-H]-.

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. 65001-21-0, 5-Bromopyridine-3-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHN, Ulrike; ELLERMANN, Manuel; STRASSBURGER, Julia; WENDT, Astrid; ROeHRIG, Susanne; WEBSTER, Robert Alan; SCHMIDT, Martina Victoria; TERSTEEGEN, Adrian; BEYER, Kristin; SCHAeFER, Martina; BUCHMUeLLER, Anja; GERDES, Christoph; SPERZEL, Michael; SANDMANN, Steffen; HEITMEIER, Stefan; HILLISCH, Alexander; ACKERSTAFF, Jens; TERJUNG, Carsten; (163 pag.)US2016/244437; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1001412-41-4, name is 5,7-Dichloro-1H-pyrrolo[2,3-c]pyridine, molecular formula is C7H4Cl2N2, 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. Safety of 5,7-Dichloro-1H-pyrrolo[2,3-c]pyridine

Step B: 5,7-dichloro-1 -methyl-pyrrolo[2,3-clpyridine: A solution of 5,7-dichloro-1 H-pyrrolo[2,3-c]pyridine (2 g, 10.693 mmol) in dry N,N- dimethylformamide (50 mL) was treated with sodium hydride (0.77 g, 16.04 mmol) at ambient temperature and reaction stirred for 15 min at this temperature. The reaction mixture was cooled to 0C and iodomethane (1 mL, 16.04 mmol) was added, and the mixture allowed to stir 18 hours at ambient temperature. The reaction mixture was then quenched with NH4CI saturated solution, extracted with ethyl acetate (three times), and the combined organic layer was dried over Na2S04, filtered and evaporated under vacuum. Purification by Combi flash chromatography with a column of 24g and a gradient cyclohexane:0-100% ethyl acetate to give the title compound as a yellow solid (1.8 g, 84%).

With the rapid development of chemical substances, we look forward to future research findings about 1001412-41-4.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; BIGOT, Aurelien; HALL, Roger Graham; JEANGUENAT, Andre; LUKSCH, Torsten; RENDLER, Sebastian; WO2013/156431; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 874302-76-8, 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 874302-76-8 as follows.

Weigh 61.2mg (0.06mmol) compound 39,64.3mg (0.18mmol) compound 37,9.8mg (0.08mmol) DMAP, was added to a 25ml eggplant-shaped flask, add 5ml DCM was dissolved under argon atmosphere, stirred at room temperature 48h, DCM was evaporated to dryness under reduced pressure and, add acetonitrile dissolved, purified by preparative liquid phase to give product 51.3mg

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,874302-76-8, its application will become more common.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Liu Keliang; Feng Siliang; Chen Kuncheng; Guo Xiaopeng; Meng Qingbin; Zhou Ning; (23 pag.)CN104370862; (2019); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84487-10-5, Adding some certain compound to certain chemical reactions, such as: 84487-10-5, name is 2-Amino-4-bromo-3-nitropyridine,molecular formula is C5H4BrN3O2, 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 84487-10-5.

Step 1 (0852) A solution of 4-bromo-3-nitropyridin-2-amine (LXVI) (5.00 g, 22.9 mmol, 1.00 eq), (2-fluorophenyl)boronic acid (LXVII) (3.82 g, 27.5 mmol, 1.20 eq), Pd(PPh3)4 (1.32 g, 1.14 mmol, 0.05 eq), and Na2CO3 (4.85 g, 45.8 mmol, 2 eq) in a mixture of toluene (25 mL), H2O (9 mL) and EtOH (6 mL) was stirred at 75 C. for 15 h under nitrogen atmosphere. The reaction mixture was the washed with brine (50 mL) and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resultant residue was purified by chromatography on silica gel (PE:EtOAc=3:1) to give 4-(2-fluorophenyl)-3-nitropyridin-2-amine (LXVIII) (4.0 g, 17.15 mmol, 74.9%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta ppm 6.29 (brs, 2H), 6.68 (d, J=4.8 Hz, 1H), 7.14 (t, J=5.2 Hz, 1H), 7.23-7.50 (m, 3H), 8.32 (d, J=4.8 Hz, 1H); ESIMS found C11H8FN3O2 m/z 234.2 (M+H).

According to the analysis of related databases, 84487-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68551; (2016); A1;,
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.18364-47-1, name is N-Methylpyridin-3-amine, molecular formula is C6H8N2, molecular weight is 108.14, as common compound, the synthetic route is as follows.HPLC of Formula: C6H8N2

Stage 13-Bromo-4-methoxy-N-methyl-N-pyridin-3-ylbenzamide An amount of 5 g (22 mmol) of 3-bromo-4-methoxybenzoic acid was dissolved in 50 ml of dichloromethane with 8.3 g (65 mmol) of diisospropylethylamine, and the solution was admixed with 5.8 g (23 mmol) of BOP-Cl and then with 2.5 g (24 mmol) of methylpyridin-3-ylamine and stirred for 2 days. The mixture was concentrated, the residue was admixed with water and aqueous sodium chloride and extracted three times with ethyl acetate, and the combined organic phases were dried and concentrated by evaporation. The residue was purified by chromatography on silica gel (cyclohexane/acetone).Yield: 5.49 g (74% of theory), 1H-NMR (D6-DMSO) 3.35 (s, 3H), 3.8 (s, 3H), 6.95 (d, 1H), 7.25 (m, 1H), 7.35 (m, 1H), 7.5 (m, 1H), 7.7 (m, 1H), 8.35 (m, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18364-47-1, N-Methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; US2010/305124; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 865156-50-9, Adding some certain compound to certain chemical reactions, such as: 865156-50-9, name is (4-Bromopyridin-2-yl)methanamine,molecular formula is C6H7BrN2, 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 865156-50-9.

d) N-(4-Bromopyridin-2-ylmethyl) formamide; 20. 00 g of C-(4-bromopyridin-2-yl)methylamine are taken up in 60 ml of formic acid and the solution is heated to reflux over 3 hours. The reaction solution is cooled to room temperature and concentrated by evaporation, and the residue is taken up in saturated aqueous sodium hydrogencarbonate solution {300 mu) and the aqueous solution is extracted with dichloromethane (3×300 mi). The combined organic phases are washed with water (300 mi), dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F)

According to the analysis of related databases, 865156-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 829-45-8, Methyl 3-(4-Pyridyl)-3-oxopropanoate, 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, HPLC of Formula: C9H9NO3, blongs to pyridine-derivatives compound. HPLC of Formula: C9H9NO3

General procedure: A solution of the amidine 6 (1.1 equiv, 276 mg, 1.23 mmol) and the beta-ketoester 8a (1 equiv, 200 mg, 1.12 mmol) in nBuOH (3 mL) was stirred at 110 C for 18 h. During this time a solid precipitate formed. After cooling to room temperature, the solid was filtered off and air-dried to provide 9a (190 mg, 48%) as a pale yellow solid;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,829-45-8, Methyl 3-(4-Pyridyl)-3-oxopropanoate, and friends who are interested can also refer to it.

Reference:
Article; Large, Jonathan M.; Torr, Jane E.; Raynaud, Florence I.; Clarke, Paul A.; Hayes, Angela; Stefano, Francesca Di; Urban, Frederique; Shuttleworth, Stephen J.; Saghir, Nahid; Sheldrake, Peter; Workman, Paul; McDonald, Edward; Bioorganic and Medicinal Chemistry; vol. 19; 2; (2011); p. 836 – 851;,
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. 101079-63-4, name is 2,6-Dichloropyridine-3,4-diamine. A new synthetic method of this compound is introduced below., name: 2,6-Dichloropyridine-3,4-diamine

To a solution of intermediate 13 (16.00 g, 89.88 mmol) in EtOH (60 mL) was added triethyl orthoacetate (50 mL) and conc. HCl (4 mL) and the mixture was stirred at 100 C for 16 hours. The mixture was concentrated and diluted with water and ethyl acetate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by column chromatography over silica gel (mobile phase gradient: from 100% petrol, 0% EtOAc to 0% petrol, 100% EtOAc). The product containing fractions were collected and the solvent was evaporated to give 11 g of intermediate 14 (57% yield, yellow solid).

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, 101079-63-4, 2,6-Dichloropyridine-3,4-diamine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; PILATTE, Isabelle, Noelle, Constance; QUEROLLE, Olivier, Alexis, Georges; ANGIBAUD, Patrick, Rene; BERTHELOT, Didier, Jean-Claude; COUPA, Sophie; DEMESTRE, Christophe, Gabriel, Marcel; MEERPOEL, Lieven; MERCEY, Guillaume, Jean, Maurice; MEVELLEC, Laurence, Anne; MEYER, Christophe; PASQUIER, Elisabeth, Therese, Jeanne; PONCELET, Virginie, Sophie; (104 pag.)WO2017/216293; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65156-94-7, Adding some certain compound to certain chemical reactions, such as: 65156-94-7, name is 5-Chloro-1H-pyrrolo[3,2-b]pyridine,molecular formula is C7H5ClN2, 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 65156-94-7.

A mixture of 5-chloro-lH-pyrrolo[3,2-b]pyridine (1 g, 6.55 mmol, 1 equiv), 1,1,1- trifluoro-2-iodoethane (1.4 g, 6.55 mmol, 1 equiv) and CS2CO3 (2.1 g, 6.55 mmol, 1 equiv) in 10 mL of DMF was stirred for 4 hours at 60 C. The reaction was then quenched by the addition of 30 mL of water, extracted with 10 mL of ethyl acetate and the combined organic layers concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petr oleum ether (1/10) to afford the desired final product as a colorless oil in 42% yield.

According to the analysis of related databases, 65156-94-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 874959-68-9 , The common heterocyclic compound, 874959-68-9, name is 5-Bromopyridine-2-sulfonyl chloride, molecular formula is C5H3BrClNO2S, 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.

Example 58(a) l-(5-Bromo-pyridine-2-sulfonyl)-4-methyl-piperazine; 5-Bromopyridine-2-sulfonyl chloride (as described in Example 52(b) (55.0 mg, 0.214 mmol) was dissolved in CH2Cl2 (1 mL) and 1-methyl-piperazine (26 muL, 0.236 mmol) was added. Stirring was continued at room temperature for 3 hours and saturated aqueous NaHCO3 (1 mL) was added. The mixture was diluted with CH2Cl2 (5 mL) and the aqueous phase was extracted with CH2Cl2 (3 x 5 mL). The combined organic phases were dried (Na2SO4) and concentrated to afford the title compound (61 mg, 89%). 1H NMR (400 MHz, CDCl3) delta ppm 2.29 (s, 3 H) 2.33 – 2.38 (m, 2 H) 2.45 – 2.50 (m, 2 H) 3.10 – 3.18 (m, 2 H) 3.30 – 3.37 (m, 2 H) 7.31 (d, J=4.29 Hz, 1 H) 7.81 (d, J=7.58 Hz, 1 H) 8.04 (dd, J=8.34, 2.27 Hz, 1 H); MS (ESI) m/z 321 (M + 1).

The synthetic route of 874959-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/2244; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem