Pyridine-derivatives

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. 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde. A new synthetic method of this compound is introduced below., Quality Control of 2-Fluoropyridine-5-carbaldehyde

Intermediate 8.2- ^S-formylpyridm-2-ylV3-azaspi- |’5.51undecan-9-yl)aSodium bicarbonate (2.70 g, 5 equiv), 2-fluoropyridine-6-carboxaldehyde (0.80 g, 1 equiv) and the hydrochloride salt of 3-azaspiro[5.5]undec-9-ylacetic acid (1.59 g, 1 equiv) were stirred at 80 C in NMP (12 mL) for 5 hours. The mixture was cooled to room temperature, acidified with 1 M HCl (25 mL, 4 equiv), diluted with water, and extracted with dichloromethane. The combined organic layers were concentrated in vacuo and purified by silica gel chromatography (0% acetone:dichloromethane to 50% acetoneidichloromethane) to give the pure aldehyde as a white solid: [ H]+ m/z 317.

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, 677728-92-6, 2-Fluoropyridine-5-carbaldehyde.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CERNAK, Timothy, A.; BALKOVEC, James, M.; NARGUND, Ravi, P.; REITER, Maud; SPERBECK, Donald, M.; DYKSTRA, Kevin, D.; YU, Yang; DREHER, Spencer; MALONEY, Kevin, M.; WU, Zhicai; DEVITA, Robert, J.; VERRAS, Andreas; WO2012/9217; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13466-38-1, Adding some certain compound to certain chemical reactions, such as: 13466-38-1, name is 5-Bromopyridin-2-ol,molecular formula is C5H4BrNO, 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 13466-38-1.

(i) 5-bromo-l-ethylpyridin-2(lH)-onePotassium tert-butoxide (328 mg) was added to 5-bromopyridin-2(lH)-one (509 mg) in dimethoxyethane (15 mL) at 20C under an atmosphere of nitrogen and stirred for 30 min. Potassium carbonate (283 mg) and iodoethane (0.236 mL) were added to the reaction mixture and the resulting suspension was stirred at 95C for 3 h. The reaction mixture was cooled and filtered, evaporated to dryness and redissolved in dichloromethane, and washed with 0.1M hydrochloric acid. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford an oil which was purified by chromatography on silica eluting with 30 to 50% ethyl acetate in z’sohexane. Pure fractions were evaporated to dryness to afford the subtitled compound (367 mg).1H NMR (500 MHz, DMSO) delta 8.04 (d, IH), 7.50 (dt, IH), 6.35 (d, IH), 3.88 (q, 2H), 1.19 (t, 3H). m/e (APCI+) 204 [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. 13466-38-1, 5-Bromopyridin-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; KINCHIN, Elizabeth; MATHER, Andrew; METE, Antonio; MILLICHIP, Ian; STANIER, Andrew Geoffrey; WO2011/154677; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17874-79-2 ,Some common heterocyclic compound, 17874-79-2, molecular formula is C8H7NO4, 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.

5-(methoxycarbonyl)pyridine-2-carboxylic acid (100 mg, 0.55 mmol) was dissolved in acetonitrile (1 mL). Triethylamine (0.230 mL, 1.66 mmol) and O-benzotriazol-1-yl- tetramethyluronium hexafluorophosphate (314 mg, 0.83 mmol) were added. The reaction mixture was stirred at rt for 5 min. 3,3,3-trifiuoropropylamine hydrochloride (83 mg, 0.55 mmol) was added and the reaction mixture was stirred at ambient temperature for 2h. The solvent was removed in vacuo and the crude was partioned between ethyl acetate and IM sodium hydroxide. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude was purified by column chromatography using a gradient of ethyl acetate in heptane yieded 38 mg (25%) of the title compound as a white solid; 1H NMR (400 MHz, DMSOtZ6) delta ppm 9.17 (t, 1 H), 9.11 (d, 1 H), 8.48 (dd, 1 H), 8.18 (d, 1 H), 3.92 (s, 3 H), 3.53 – 3.60 (m, 2 H), 2.54 – 2.66 (m, 2 H); MS (ESI) m/z 277 [M+H+], m/z 275 [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. 17874-79-2, 5-(Methoxycarbonyl)picolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2008/130320; (2008); A2;,
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. 13362-28-2, name is 2-Amino-4-pyridinecarboxylic acid, molecular formula is C6H6N2O2, 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. Quality Control of 2-Amino-4-pyridinecarboxylic acid

Methanol solution (1.8L) of 2-aminoisonicotinic acid (207g, 1.5mol) was added to thionyl chloride (238g, 2mol) at 50C by dropping. The solution was stirred for 5 more hours at the same temperature. Then, the solvent was removed under reduced pressure, and saturated aqueous solution of sodium carbonate was added to the residue to be basic of pH=9-10. After extracting the mixed solution by using dichloromethane (3*300ml), organic layer was collected and dried by using anhydrous sodium sulfate. The solvent was concentrated to obtain methyl 2-aminoisonicotinate (189g, 83%) (Compound 2) of yellow solid. [0518] 1H-NMR (d6-DMSO, 300MHz): delta3.96 (S, 3H) ; 7.14 (d, 1H); 7.49(br, 1H); 8.07(d, 1H); 8.18 (br, 2H, NH).

With the rapid development of chemical substances, we look forward to future research findings about 13362-28-2.

Reference:
Patent; Shin Nippon Biomedical Laboratories, Ltd.; SUZUKI, Nobuyuki; YAMASHITA, Hidetoshi; (156 pag.)EP3018125; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1190862-72-6, Adding some certain compound to certain chemical reactions, such as: 1190862-72-6, name is 5-Bromo-6-methylnicotinic acid,molecular formula is C7H6BrNO2, 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 1190862-72-6.

5-Bromo-6-methyl – nicotinic acid (0.20 g, 0.93 mmol) and 4-(4-methyl – piperazinyl small-ylmethyl) -3-trifluoromethyl – phenylamine (0.23g, 0.85 mmol ) was dissolved in N, N- dimethylformamide (10 mL), were addedunder ice-cooling 2 – (; 7-aza-benzotriazole) -Nu, Nu, Nu ‘, Nu’- tetramethylhexafluorophosphate (0.39 g, 1.02 mmol) and diisopropylethylamine (0.20 mL,1.27 mmol), and stirring was continued overnight. The reaction mixture waspoured into water, extracted with ethyl acetate, the organic phaserespectively, 5% dilute hydrochloric acid, saturated sodium bicarbonatesolution, washed with water and saturated brine, dried over anhydrous sodiumsulfate, and concentrated under reduced pressure, silica gel columnchromatography to give 5-bromo-6-methyl -N- [4- (4- methyl -piperazin-1-ylmethyl) -3-trifluoromethyl – phenyl] – nicotinamide (yellowsolid, 0.26 g ), yield 65%.

According to the analysis of related databases, 1190862-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Pharmaceuticals Holding Co.,Ltd .; WAN, HUIXIN; LI, CHUNLI; SHI, Chen; Liu, Haiyan; Li, Ping; XIA, Guangxin; HAN, Yanan; (52 pag.)CN103420977; (2016); B;,
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. 5350-93-6, name is 6-Chloropyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Chloropyridin-3-amine

Reference Example 134 6-Chloropyridin-3-ylsulfonyl chloride Under ice-cooling, thionyl chloride (12 mL) was added dropwise over 1 hr to water (70 mL) and the mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Under ice-cooling, 5-amino-2-chloropyridine (5.0 g) was added to concentrated hydrochloric acid (40 mL) and the mixture was stirred. An aqueous solution (12.5 mL) of sodium nitrite (2.88 g) was added dropwise while keeping the inside temperature at not higher than 5°C, and the mixture was further stirred for 15 min. The reaction mixture was gradually added at 5°C to the above-mentioned sulfur dioxide-containing solution added with cuprous chloride (70 mg). Under ice-cooling, the mixture was further stirred for 30 min. The precipitate was collected by filtration, and washed with water and ethanol to give the title compound (yield 4.79 g, 58percent). 1H-NMR (CDCl3)delta: 7.60-7.63 (1H, m), 8.24-8.27 (1H, m), 9.03-9.04 (1H, m).

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, 5350-93-6, 6-Chloropyridin-3-amine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Kajino, Masahiro; Hasuoka, Atsushi; Tarui, Naoki; Takagi, Terufumi; EP2336107; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 26452-80-2 ,Some common heterocyclic compound, 26452-80-2, molecular formula is C5H3Cl2N, 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 B Preparation of 2,4-dichloro-3-pyridine Carboxaldehyde Under nitrogen, a solution of 1.6 g of 2,4-dichloropyridine in 5 mL dry tetrahydrofuran (THF) was added to a solution of 6 mL of lithium diisopropyl amide in 25 mL of THF at -70 C., followed by stirring at this temperature for 3 hours. Then 1 mL of dry N,N-dimethylformamide was added at -70 C. followed by stirring at this temperature for 1 hour. Then 25 mL of saturated ammonium chloride solution was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with 25 mL of water and extracted with ethyl acetate (2*). The combine organic phases were distilled under vacuum to give solids that were dissolved in 5 mL of methylene chloride and filtered through silica gel, eluding with 100% methylene chloride. Removal of the solvent under vacuum provided the title intermediate as a solid. 1H NMR (CDCl3; 300 MHz) delta7.41 (d, 1H, J is 5.3 Hz), 8.42 (d, 1H, J is 5.2 Hz), 10.5 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26452-80-2, its application will become more common.

Reference:
Patent; Neubert, Timothy Donald; Piotrowski, David Walter; Walker, Michael Paul; US2004/44040; (2004); 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. 110651-92-8, name is 7-Chloro-6-nitrothieno[3,2-b]pyridine, molecular formula is C7H3ClN2O2S, 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. HPLC of Formula: C7H3ClN2O2S

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (156 mg, 0.727 mmol), [(5S)- 5-amino-5,6-dihydro-2H-pyran-2-yl]methyl acetate (129 mg, 0.754 mmol) and N,N- diisopropylethylamine (0.26 mL, 1.5 mmol) in isopropyl alcohol (1.7 mL) was heated at 90 C for 2 h. The reaction mixture was concentrated and purified with flash chromatography to give the desired product (0.21 g 83%). LCMS calculated for CisHieNsOsS (M+ H)+: m/z = 350.1 ; Found: 350.0.

With the rapid development of chemical substances, we look forward to future research findings about 110651-92-8.

Reference:
Patent; INCYTE CORPORATION; SCHERLE, Peggy A.; LIU, Xuesong; WO2015/157257; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)pyridine, 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: C6H2Cl2F3N, blongs to pyridine-derivatives compound. HPLC of Formula: C6H2Cl2F3N

Powdered potassium hydroxide (9.35 g, 0.15 mol, 3 eq. ) is placed together with 70 ml dry DMSO in a 250 ml three-necked-bottom and under dry argon atmosphere the nitromethane (6.1 g, 0.1 mol, 2 eq) solved in 30 ml dry DMSO is added within 30 min slowly with mechanical stirring while cooling with an ice bath to maintain the temperature at 20 C. STIRRING of the reaction mixture at 20C is continued for additional 15 min. Then 2,3-dichloro-5-trifluoromethylpyridine (10.80 g, 0.05 mol, 1 eq. ) is added as one portion without endo-or exothermic reaction. The mixture is heated to 50 C, stirred for 3 h at this temperature and then allowed to cool to room temperature. The dark brown crude product is poured into 500 ml of water, acidified by addition of diluted hydrochloric acid and followed by three extractions with 50 ml ethyl acetate each. The combined organic layers are washed with three 30 ml portions of water and are subsequently dried over anhydrous sodium sulphate. After filtration the solvent is removed at 20C and under 150 mbar reduced pressure. Yield: 9.72 g 3-chloro-2-nitromethyl-5-trifluoromethylpyridine (73.9 % theoretical yield, 91. 4 % purity)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; WO2004/96772; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113975-22-7, 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. 113975-22-7, name is 2-Fluoro-3-iodopyridine, molecular formula is C5H3FIN, 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.

Di-i-propylamine (260.9 mg, 364.4 muL, 2.578 mmol) was dissolved in dryTHF (1.900 mL) and cooled to -700C. n-BuLi (986.4 muL of 2.5 M, 2.466 mmol) was added slowly dropwise, and the resultant mixture was stirred at 00C for -2 minutes and recooled to -700C. A solution of 2-fluoro-3-iodo-pyridine (500 mg, 2.242 mmol) in dry THF (1.400 mL) was added slowly dropwise and the resultant was stirred at -700C for -2.5 hours. 2,2,2-trifluoroacetaldehyde was added via cannula (bp. is – 200C) and the resultant mixture was stirred at -700C for ~1.5 hours. The reaction was quenched at -700C by the rapid addition of water (~2mL) and the resulting mixture was partitioned with EtOAc. The aqueous phase was extracted with EtOAc (3 x 2OmL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a mobile light brown oil (581.7mg). The resulting mixture was purified by column chromatography (5% EtOAc in DCM, -10OmL silica, loaded in DCM) to give a slightly yellow gum that solidified under high-vacuum to give a light yellow solid (225.2mg, 31% Yield).

According to the analysis of related databases, 113975-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/73300; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem