Category: pyridine-derivatives

Product Details of 39901-94-5. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Picolinoyl chloride hydrochloride, is researched, Molecular C6H5Cl2NO, CAS is 39901-94-5, about A new pathway via intermediate 4-amino-3-fluorophenol for the synthesis of regorafenib. Author is Du, Fangyu; Zhou, Qifan; Shi, Yajie; Yu, Miao; Sun, Wenjiao; Chen, Guoliang.

A practical synthetic route to regorafenib, in which the target compound was obtained via a 10-step synthesis starting from 2-picolinic acid, 4-chloro-3-(trifluoromethyl)aniline and 3-fluorophenol was reported. Crucial to the strategy was the preparation of 4-amino-3-fluorophenol via Fries and Beckman rearrangements using an economical and practical protocol. The main advantages of the route include inexpensive starting materials and an acceptable overall yield. A scale-up experiment was carried out to provide regorafenib with 99.96% purity in 46.5% total yield.

Here is a brief introduction to this compound(39901-94-5)Product Details of 39901-94-5, if you want to know about other compounds related to this compound(39901-94-5), you can read my other articles.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called A novel crystal structure of {tris[4-(1H-pyrazol-3-yl-κN2)-3-azabut-3-enyl]amine-κN}iron(II) bis(tetrafluoridoborate) methanol monosolvate featuring a low-spin configuration, published in 2015-12-01, which mentions a compound: 948552-36-1, Name is 1H-Pyrazole-5-carbaldehyde, Molecular C4H4N2O, Electric Literature of C4H4N2O.

Mononuclear complexes are good model systems for evaluating the effects of different ligand systems on the magnetic properties of iron(II) centers. A novel crystal structure of the title compound, [Fe(C18H24N10)](BF4)2·CH3OH, with one mol. of methanol per formula unit exhibits a strictly sixfold coordination sphere associated with a low-spin configuration at the metal center. The incorporated methanol solvent mol. promotes extended hydrogen-bonding networks between the tetrafluoridoborate anions and the cationic units. A less constrained crystal structure regarding close contacts between the tetrafluoridoborate anions and the cationic units allows a spin transition which is inhibited in the previously published hydrate of the title compound

Here is a brief introduction to this compound(948552-36-1)Electric Literature of C4H4N2O, if you want to know about other compounds related to this compound(948552-36-1), you can read my other articles.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 13729-77-6, is researched, Molecular C6H12ClNO, about Synthesis of some N-substituted 2-methyl- and 3-methyl-4-piperidones, the main research direction is PIPERIDONES.Category: pyridine-derivatives.

cf. CA 60, 15825b. 1,2-Dimethyl-4-piperidone-MeI (I) heated with Me2C(NH2)CCH (Ia) in H2O 3.5 hrs. at 80° in a sealed tube and kept 2 days at room temperature gave a low yield of 1-(1,1-dimethyl-2-propynyl)-2-methyl-4-piperidone (II), m. 50-2°. I treated with ice-cold KOH gave 42% Me2NCH2CH2COCH:-CHMe, b2 46-7°, n19.5D 1.4593, which with MeI in Me2CO gave the methiodide, a solid, which with Ia, finally at 80°, gave 72% II. To 287 g. AlCl3 in CHCl3 was added 227 g. ClCH2CH2COCl followed at -20° by MeCH:CH2 passed in for 2.5 hrs., after which an aqueous treatment gave mixed chlorides, b8 94-5°, which with Ia in aqueous K2CO3, finally 10 hrs. at 80°, gave some II. Keeping CH2:CHCO2Me with MeCH(NH2)CH2CO2Et 2 days gave 69.5% MeO2CCH2CH2NHCHMeCH2CO2Et, b6 127-30°, n17D 1.4410, which with Na in liquid NH3, followed by an aqueous treatment, gave after acidification and heating to expel CO2, treatment with KOH and extraction with CHCl3, 43% 2-methyl-4-piperidone, isolated as N-benzoyl derivative, m. 88°, and as HCl salt. The HCl salt and tosyl chloride in pyridine 1 day gave 1-(p-tolylsulfonyl)-2-methyl-4-piperidone, m. 80-1°. Similarly was prepared 1-(p-tolylsulfonyl)-3-methyl-4-piperidone (III), m. 104-5°. Heating MeO2CCH:CH2 with MeCH(NHMe)CH2CO2Et 12 hrs. at 52° gave 53% MeO2CCH2CH2NMeCHMeCH2CO2Et, b6 129-30°, n17D 1.4420, which with Na in liquid NH3, then with aqueous HCl, gave 76% 1,2-dimethyl-4-piperidone, b7 55-7°, n18D 1.4592. III heated 8 hrs. with KOH and cyclohexylamine gave traces of N-cyclohexyl-3-methyl-4-piperidone; Me3CNH2 with KOH also gave traces of the N-tert-butyl derivative

Here is a brief introduction to this compound(13729-77-6)Category: pyridine-derivatives, if you want to know about other compounds related to this compound(13729-77-6), you can read my other articles.

Reference:
Pyridine – Wikipedia,
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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 625-82-1, is researched, Molecular C6H9N, about Construction of pyridine-boron dipyrromethene dye and application in picrate recognition, the main research direction is pyridine boron dipyrromethene dye picrate recognition.Name: 2,4-Dimethyl-1H-pyrrole.

3-Pyridine formaldehyde and 2,4-di-Me pyrrole as raw materials, fluorescent probe mPBP was synthesized based on pyridine-boron dipyrromethene dye. The structure of probe was characterized by 1HNMR and ESI-MS. Fluorescent probe has good selectivity and sensitivity of PA in water containing 80% DMSO aqueous solution Probe mPBP can react with PA completely less than 30 s, can quickly and effectively identify PA, can meet the requirements of on-site rapid detection of recognition. The fluorescence probe mPBP showed a good linear relationship with different concentrations of PA, and the limit of detection was 12.58 nmol/L. Probe mPBP successful applied in river water samples to add the PA content detection, obtained the very good recovery rate (96.0%∼105.0%). In addition, the color change of the solution was very obvious (light green to colorless), which can be used as a quick visual identification of PA-chemosensor in a complex environment sample.

Here is a brief introduction to this compound(625-82-1)Name: 2,4-Dimethyl-1H-pyrrole, if you want to know about other compounds related to this compound(625-82-1), you can read my other articles.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Fresenius Environmental Bulletin called Photoelectrochemical reduction of CO2 to methanol at pyridinyl-immobilized CuInS2 thin film electrode, Author is Yuan, Jiongliang; Fan, Mingming; Yang, Liangwen; Hao, Cunjiang, which mentions a compound: 39901-94-5, SMILESS is O=C(Cl)C1=NC=CC=C1.[H]Cl, Molecular C6H5Cl2NO, Formula: C6H5Cl2NO.

A pyridinyl-immobilized CuInS2 thin film is developed, and the coverage of pyridinyl group on CuInS2 thin film is investigated. Using the immobilized CuInS2 thin film as the photocathode, the solar-driven photoelectrochem. reduction of CO2 to methanol is studied. Methanol yield reaches the maximum at the underpotential of 72 mV at pH 4.4, and Faraday efficiency for methanol is 98%. In addition, pyridinyl-immobilized thin film is stable for 10 h. The diffusion of CO2 might be the rate determining step in photoelectrochem. reduction of CO2, and methanol yield increases by 6.6 times when using semi immersion electrode. Therefore, it is expected that the gas diffusion electrode can enhance methanol yield significantly.

Here is a brief introduction to this compound(39901-94-5)Formula: C6H5Cl2NO, if you want to know about other compounds related to this compound(39901-94-5), you can read my other articles.

Reference:
Pyridine – Wikipedia,
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Electric Literature of 915006-52-9, 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 915006-52-9 as follows.

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%). To a mixture containing 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) and Intermediate 5A-2 (100 mg, 0.29 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (111 mg, 0.36 mmol), and Pd(dppf)C12 (10.5 mg, 0.014 mmol) in a screw cap vial was added THF (2.5 mL) followed by 3M aqueous solution of tripotassium phosphate (0.10 mL, 0.3 mmol). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 75 C. for 3 h. The reaction mixture was cooled to room temperature and treated with saturated aqueous NaCl solution (5 mL) and extracted with ethyl acetate (3*10 mL). The extracts were combined, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in a small amount of DCM and purified on silica gel column chromatography eluting with a 10 min gradient from 5%-100% DCM/EtOAc. No separation was observed. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate was isolated (100 mg, 77% yield), m/z (550, M+1) and was used as such in subsequent step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,915006-52-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); 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.1193-71-1, name is 4,6-Dimethylpyridin-3-amine, molecular formula is C7H10N2, molecular weight is 122.17, as common compound, the synthetic route is as follows.Formula: C7H10N2

4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (247 mg, 0.819 mmol) was added to a solution of triethylamine (0.114 mL, 0.819 mmol) and 4,6-dimethyl-3-pyridinamine (100 mg, 0.819 mmol) in dichloromethane (1 mL). The mixture was heated at 70 C. for 2 hours. To the mixture was added water (5 mL) then the organic layer separated and purified by silica (Si) chromatography (100% ethyl acetate). The relevant fractions were combined and concentrated to give the title product (310 mg) as a yellow solid. LCMS (2 min, formic) Rt 0.63 mins, m/z (ES+) 388 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-71-1, 4,6-Dimethylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Glaxo Group Limited; Birault, Veronique; Campbell, Amanda Jennifer; Harrison, Stephen; Le, Joelle; Shukla, Lena; US2015/65507; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63237-88-7, Adding some certain compound to certain chemical reactions, such as: 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid,molecular formula is C8H6N2O2, 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 63237-88-7.

To a solution of pyrazolo[1,5-a]pyridine-2-carboxylic acid (2.40 mg, 14.8 mumol) and 8 (6.00 mg, 14.8 mumol) in anhydrous DMF (1 mL) was added DIPEA (5.00 muL, 29.6 mumol) and HATU (5.90 mg, 15.5 mumol). After stirring the reaction mixture at room temperature for 16 h the solvent was removed under reduced pressure. The crude mixture was suspended in aqueous 5% NaHCO3 solution and extracted with ethyl acetate (3*). The combined organic phases were washed with water and brine and were dried (MgSO4). After removal of solvents under reduced pressure the crude material was purified by preparative HPLC (acetonitrile in 0.1% aqueous HCOOH, 5% to 95%) to give 3 (2.25 mg, 28%) as a colorless solid. 1H NMR (600 MHz, CDCl3) delta 8.38-8.34 (m, 1H), 7.61-7.57 (m, 1H), 7.31 (br t, J = 5.2 Hz, 1H), 7.16 (ddd, J = 8.9, 6.7, 1.0 Hz, 1H), 7.07 (d, J = 0.6 Hz, 1H), 6.87 (td, J = 6.9, 1.3 Hz, 1H), 6.60 (s, 1H), 3.75 (br s, 4H), 3.55 (app q, J = 6.6 Hz, 2H), 2.55 (br s, 4H), 2.48 (br s, 2H), 1.77-1.61 (m, 4H), 1.36 (s, 9H); 13C NMR (150 MHz, CDCl3) delta 177.7, 162.2, 154.9 (q, JCF = 33.7 Hz), 148.0, 141.4, 128.3, 123.7, 121.3 (q, JCF = 275 Hz), 119.3, 113.6, 98.0, 95.6 (q, JCF = 3.4 Hz), 57.9, 52.7, 43.8, 39.5, 39.1, 29.7, 29.4, 27.6, 24.2; ESI-MS m/z 504.3 [M+H]+; HRMS-ESI (m/z): [M+H]+: calcd. for C25H33F3N7O: 504.2693, found: 504.2688; HPLC: System 1: tR = 16.3 min, purity 99%, System 2: tR = 16.2 min, purity 99%.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Stoessel, Anne; Brox, Regine; Purkayastha, Nirupam; Huebner, Harald; Hocke, Carsten; Prante, Olaf; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3491 – 3499;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 956010-87-0, 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 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1(2)3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine 7-oxide (1b)Compound (1a) was dissolved in ethylene glycol dimethyl ether (100 mL) and heptane (200 mL), and m-chloroperoxybenzoic acid (33.9 g) was added to the resulting solution at 0 C., followed by stirring at room temperature for 1 hr. The precipitate was collected by filtration to obtain compound (1b) (33.3 g, 96%) as a white solid.1H-NMR (DMSO-d6) delta 8.53 (1H, d, J=6.1 Hz), 8.87 (1H, d, J=8.3 Hz), 7.36 (1H, dd, J=8.3, 6.1 Hz); LRMS (ESI) m/z 204 [M+H]+.

According to the analysis of related databases, 956010-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 61494-55-1, 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 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows.

INTERMEDIATE 52-[(2-Fluoro-4-iodophenyl)amino1thienor2,3-&]pyridine-3-carboxylic acidTo a stirred solution of diisopropylamine (35.3 mL, 250 mmol) in anhydrous THF (200 mL) cooled to -150C was added rc-butyllithium (100 mL, 2.5M in hexanes, 250 mmol) slowly such that an internal temperature of between -10 and 00C was maintained. The resultant mixture was stirred at room temperature for 15 minutes before being cooled to O0C. The solution of lithium diisopropylamide was added via cannula to a rapidly stirred suspension of (2-chloropyridin-3-yl)acetic acid (Intermediate 3; 21.4 g, 125 mmol) in anhydrous THF (400 mL) at 00C. The temperature of the reaction mixture was maintained at 00C over the course of the addition. Upon complete addition of the lithium diisopropylamide solution the resultant bright yellow suspension was stirred at 00C for 15 minutes. A solution of Intermediate 4 (34.9 g, 125 mmol) in anhydrous THF (200 mL) was then added to the reaction mixture via cannula and the mixture heated to 65 C for 18 hours. The reaction mixture was cooled and the volatiles removed in vacuo. The resultant brown gum was redissolved in THF (200 mL), cooled to O0C and 10% aqueous acetic acid (500 mL) added slowly. Acetonitrile (-200 mL) was added slowly until a brown solid developed; the solid was isolated by filtration and washed with successive portions of diethyl ether and acetonitrile to give the title compound as a yellow crystalline solid (11.0 g, 21%). ?H (DMSOd6) 8.42 (IH, d, J 6.7 Hz), 8.22 (IH, m), 7.73 (IH, m), 7.61 (IH, m), 7.46 (IH, t, J8.6 Hz), 7.35-7.31 (IH, m). Exchangeable protons were not observed. LCMS (pH 10) RT 1.82 minutes, ES+ 415 (M+H)+, ES” 413 (M-H)”.

According to the analysis of related databases, 61494-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; WO2009/13462; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem