Category: pyridine-derivatives

Adding some certain compound to certain chemical reactions, such as: 1849-53-2, name is 3-Methoxypicolinaldehyde, 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 1849-53-2. 1849-53-2

3-Methoxypicolinaldehyde (0.117 g, 0.850 mmol) and sodium 1-(trifluoromethyl)cyclopropane-1-sulfinate (0.500 g, 2.55 mmol) were dissolved in diethylcarbonate (5.1 mL) and water (3.4 mL), and the mixture was cooled to 0 C. tert-Butyl hydroperoxide (70% aqueous, 0.547 g, 4.25 mmol) was then added dropwise. The reaction was stirred in the ice bath for 5 minutes and was then heated at 90 C. for 2 hours. After this time, the mixture was cooled to room temperature, quenched with saturated aqueous Na2S2O3 solution (10 mL), and diluted with ethanol (20 mL). The mixture was concentrated in vacuo, and the resulting material was taken up in 20% CH3OH-ethyl acetate and filtered through a pad of silica gel on a fritted glass funnel, eluting with 10% CH3OH-ethyl acetate. The combined filtrates were concentrated in vacuo, and the residue was purified by silica gel chromatography, eluting with 40% ethyl acetate-heptanes to 100% ethyl acetate (gradient). The title compound was obtained, 0.0253 g, 12% yield. 1H NMR (400 MHz, CDCl3) delta ppm 10.35 (s, 1H), 8.47 (s, 1H), 7.50 (s, 1H), 4.02 (s, 3H), 1.53 (m, 2H), 1.28 (m, 2H); MS (ESI+) m/z 246.1 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1849-53-2.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Greszler, Stephen N.; Housseman, Christopher Gaetan; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (263 pag.)US2018/99931; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

128071-75-0, 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. 128071-75-0, name is 2-Bromonicotinaldehyde, molecular formula is C6H4BrNO, 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.

2-Bromo-3-vinylpyridine. See Spivey, A. C.; Shukla, L.; Hayler, J. F. Org. Lett. 2007, 9, 891-894. Butyllithium (22.75 mL, 59.1 mmol) was added to the THF (450 mL) suspension of methyltriphenylphosphonium bromide (21.13 g, 59.1 mmol) at 0 C. The solution turned to orange and the reaction was lift to room temperature for 30 min before cooled it back to 0 C. 2-bromonicotinaldehyde (10 g, 53.8 mmol) in 50 mL THF was added through canula to the reaction solution. The precipitate was formed and the reaction was lift to room temperature. The color of the reaction turned to green, gray. After a while, the color of the reaction became orange again. The reaction was stirred at room temperature over weekend. The solvent was removed mostly via vacuum and the crude was partitioned between water and diethyl ether. The organic layer was separated and the aqueous layer was extract twice with diethyl ether. The diethyl ether layer was combined, dried (Na2SO4), filtered and concentrated. The product was obtained by flash column eluted with ethyl acetate in hexane (10%) as yellow oil (8.78 g, 89%). MS(ESI)[M+H+]=184.04; 1H NMR delta ppm (400 MHz, CHLOROFORM-d) 8.21-8.29 (m, 1H) 7.78 (dd, J=7.68, 1.89 Hz, 1H) 7.20-7.28 (m, 1H) 6.96 (dd, J=17.37, 11.08 Hz, 1H) 5.72 (d, J=17.37 Hz, 1H) 5.46 (d, J=11.08 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 128071-75-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/258866; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0, 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 766-11-0, name is 5-Bromo-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of lithium di-iso-propylamine (5 mL, 35 mmol) in anhydrous THF (40 mL) was cooled to -78 C. under nitrogen and n-butyl lithium (2.5 M in hexanes, 12 mL, 30 mmol) was added. The mixture was then stirred at -78 C. for 15 min before 5-bromo-2-fluoro-pyridine (5 g, 28 mmol) was added. The resulting mixture was then stirred at -78 C. for 90 min. N-formylpiperidine (4 mL, 36 mmol) was added very rapidly to the suspension at -78 C. and the mixture stirred vigorously for 60 sec. The reaction was immediately quenched by the addition of a 10% (w/v) aqueous solution of citric acid. The mixture was warmed to room temperature and distributed between water and dichloromethane. The aqueous phase was extracted three times with dichloromethane and the organic phases were combined, dried over sodium sulfate, filtered and concentrated. Crystallization of the crude product from cyclohexane afforded 5-bromo-2-fluoro-pyridine-3-carbaldehyde (2.993 g, 52% yield) as pale beige flaky crystals. 1H-NMR (500 MHz, d6-DMSO) delta 10.07 (s, 1H), 8.70 (dd, 1H), 8.55 (dd, 1H). MS: m/z 236, 238 [MNa+], 204, 206 [MH+], 176, 178 [MH-CO+].

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 766-11-0, 5-Bromo-2-fluoropyridine.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2008/261921; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1594-58-7, 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. 1594-58-7, name is N-Hydroxynicotinimidamide, molecular formula is C6H7N3O, 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.

General procedure: Isobutyl chloroformate (0.44 g, 3.19 mmol) was added dropwise under argon to a -30 C solution of 11 (1 g, 3.19 mmol) and N-methylmorpholine (0.39 g, 3.83 mmol) in THF (40 mL). After a brief (30 min) stirring, a solution of the respective amidoxime (3.83 mmol) in THF (10 mL) was added dropwise. The reaction mixture was allowed to reach rt, stirred at that temperature for 12 h, filtered and concentrated in vacuo. The residue was dissolved in toluene (50 mL), TBAF (0.1 g) was added and the mixture was heated at reflux for 5 h with azeotropic removal of water using a Dean-Stark trap. The toluene solution was washed with water, 1% aqueous citric acid, 5% sat. aq NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated to dryness in vacuo. The residue was fractionated on silica gel using chloroform as eluent. The fractions containing the 1,2,4-oxadiazole product (according to LC MS analysis) were pooled and concentrated in vacuo. The residue was dissolved in 1,4-dioxane (15 mL) and treated with 4 M HCl in 1,4-dioxane (1 mL). After stirring at rt for 6 h, the reaction mixture was concentrated to dryness in vacuo and the residue was crystallized from isopropyl alcohol to provide analytically pure title compound.

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. 1594-58-7, N-Hydroxynicotinimidamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Krasavin, Mikhail; Lukin, Alexey; Bagnyukova, Daria; Zhurilo, Nikolay; Zahanich, Ihor; Zozulya, Sergey; Ihalainen, Jouni; Forsberg, Markus M.; Lehtonen, Marko; Rautio, Jarkko; Moore, Daniel; Tikhonova, Irina G.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5481 – 5494;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

183610-70-0, 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. 183610-70-0, name is 2-Amino-3-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, 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.

To a solution of 3-trifluoromethylpyridin-2-ylamine (Fluorochem Ltd , Derbyshire, United Kingdom 5 37 g, 32 8 mmol) in 100 ml of dry CH3CN under argon were added N- bromosuccinimide (645 g, 36 2 mmol) in 4 equal portions over a period of 1 h at 0-5C The cooling bath was removed and stirring was continued for 3 h The solvent was evaporated under vacuum, then the residue was dissolved in EtOAc and washed with water and brine The organic layer was dned over Na?SO and evaporated to give the title compound as a orange oil. (M+H = 239, 241).

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. 183610-70-0, 2-Amino-3-(trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A common compound: 108-48-5, name is 2,6-Dimethylpyridine,molecular formula is C7H9N, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 108-48-5

Reaction of 2, 6-lutidine and formaldehyde was carried out over Na-ZSM-5 (SiO2/ Al2O3 = 30) at 300C with 0.5 H W. H. S. V. The catalyst was 4 G with 18-30 mesh size and feed rate of 2 ml. H 1. The molar ratio of 2, 6-lutidine to formaldehyde 1: 4. The liquid product selectivities were 30.4 and 69. 6 % for 2, 6-DVP and 2DVP respectively, at 53.3 wt% conversion of 2,6-lutidine.

With the rapid development of chemical substances, we look forward to future research findings about 108-48-5.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; WO2004/87664; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

107504-08-5, 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.107504-08-5, name is 5-Fluoro-2-picolinic acid, molecular formula is C6H4FNO2, molecular weight is 141.1, as common compound, the synthetic route is as follows.

A mixture of compound 4-1 (20 mg, 0.056 mmol), 5-fluoropicolinic acid (18 mg, 0.112 mmol), and T3P (150 mg, 0.236 mmol, 50% in EtOAc) in THF (5 mL) was stirred at 25 C overnight. The mixture was diluted with water and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2S04, and concentrated. The residue was purified by preperative HPLC (column: Gemini 200×25 mm, 5 muiotaeta; mobile phases A: water containing 0.075% TFA, v/v; mobile phase B: CH3CN; gradient 18-48% B, 11 min, 25 mL/min) to afford Example 4a.

Statistics shows that 107504-08-5 is playing an increasingly important role. we look forward to future research findings about 5-Fluoro-2-picolinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; KAELIN, David Earl, Jr.; SCOTT, Jack, D.; WU, Wen-Lian; BURNETT, Duane, A.; WO2014/99794; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

16063-69-7, 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. 16063-69-7, name is 2,4,6-Trichloropyridine, molecular formula is C5H2Cl3N, 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 solution of diisopropylamine (2.54 g, 22. 1 mmol) and rt-butyl lithium (1.6 M in hexane, 15.7 mL, 25.1 mmol) in tetrahydrofuran (100 mL) was stirred for 30 minutes at – 78C. A solution of the product of EXAMPLE 11 B (2.0 g, 1 1.0 mmol) in tetrahydrofuran (8 mL) was added dropwise over 30 minutes, followed by stirring for 1 hour. The mixture was poured into dry ice and stirred for 1 hour at room temperature. The mixture was acidified with 10% aqueous hydrochloric acid (20 mL), diluted with an aqueous saturated sodium chloride solution and extracted with ethyl acetate. The organic layer was washed, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The solvent was removed under vacuum to give the crude title compound which was used in the next step without further purification.

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. 16063-69-7, 2,4,6-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97683; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

100-55-0, Adding a certain compound to certain chemical reactions, such as: 100-55-0, 3-Pyridinemethanol, 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, 100-55-0, blongs to pyridine-derivatives compound.

General procedure: In a 10 ml screw-capped vial was placed 2 mol% of manganese (I) catalyst, 1 equivalent of thebase, 0.1 ml of toluene , 0.2 mmol of alcohol and 0.4 mmol of amine under argon atmosphere. The reaction mixture was heated at 140C for 24 h in an oil bath. The reaction mixture was then cooledat ambient temperature, quenched with water and the organic layer was extracted with ethylacetate. The combined organic layers were dried over sodium sulfate and concentrated. 1H NMR yields were determined using 1,3,5-trimethoxy benzene as an internal standard. The product waspurified by silica gel column chromatography using the mixture of ethyl acetate and hexane aseluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100-55-0, its application will become more common.

Reference:
Article; Das, Kuhali; Kumar, Amol; Jana, Akash; Maji, Biplab; Inorganica Chimica Acta; vol. 502; (2020);,
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. 89793-09-9, name is 2-Chloro-4,6-dimethyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. 89793-09-9

Step 1, 3-{4-[(4,6-Dimethyl-3-nitro-2-pyridinyl)amino]phenyl}propanoic acid To a solution of 2-chloro-4,6-dimethyl-3-nitropyridine (17.9 g, 96 mmol) and methyl 3-(4-aminophenyl)propanoate (19 g, 96 nmol) in DMSO (100 mL) was added N,N-diisopropylethylamine (26 g, 200 mmol), and the reaction mixture was heated at 140 C. overnight. The reaction mixture was partitioned between water (400 mL) and ethyl acetate/toluene (v/v, 2:1, 300 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate/toluene (v/v, 2:1, 200 mL). The combined organic extracts were washed with brine (200 mL), dried (Na2SO4), and concentrated. To a solution of residual oil in methanol (100 mL) was added 2 N aqueous NaOH (150 mL, 300 mmol) and the resulting mixture was stirred at room temperature for 2 h. The volatile component was removed under reduced pressure and the residue was washed with ethyl acetate (200 mL). The aqueous phase was acidified with 2N hydrochloric acid (200 mL, 400 mmol) and extracted with ethyl acetate (3*200 mL). The extracts were washed with brine (200 mL), dried (Na2SO4), and concentrated to give 23.2 g (77%) of the title compound as pale brown solids. 1H-NMR (CDCl3) delta: 9.57 (1H, s), 7.56 (2H, d, J=8.4 Hz), 7.19 (2H, d, J=8.4 Hz), 6.52 (1H, s), 2.95 (2H, t, J=7.5 Hz), 2.66 (2H, t, J=7.5 Hz), 2.55 (3H, s), 2.43 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89793-09-9, 2-Chloro-4,6-dimethyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Audoly, Laurent; Okumura, Takako; Shimojo, Masato; US2002/77329; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem