Pyridine-derivatives

Electric Literature of 63071-13-6 , The common heterocyclic compound, 63071-13-6, name is 4-Chloropicolinaldehyde, molecular formula is C6H4ClNO, 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 single-neck round bottomed flask was charged with dioxane/ H2O (3/1), picolinaldehyde 16 (536mg, 5.0mmol), methyl acrylate (0.54mL, 6.0mmol) and DABCO (34mg, 0.3mmol). The reaction mixture stirred at room temperature for 3h. Then the reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (3/1) to afford 0.43g of 17 as dark yellow oil. Yield: 44.7%.

The synthetic route of 63071-13-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xue, Yu; Tang, Jingshu; Ma, Xiaozhuo; Li, Qing; Xie, Bingxue; Hao, Yuchen; Jin, Hongwei; Wang, Kewei; Zhang, Guisen; Zhang, Liangren; Zhang, Lihe; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 94 – 108;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 929022-76-4, 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 929022-76-4, name is 2-Chloro-4-fluoronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step B: Ethyl (2-chloro-4-fluoropyridin-3-yl)acetate (64-3)Intermediate 64^2 (19.9g, 108 mmol) was dissolved in CH2C12 (100 ml), added lml DMF and then added oxalyl chloride (17.2 g, 135 mmol) dropwise over 10 minutes. When gas evolution subsided (about an hour), the reaction was concentrated and azeotroped with THF (3 x 50 ml) to give the crude acid chloride. TMS-diazomethane solution (97 ml, 2.0 M, 195 mmol) was added to 300 ml 1 : 1 THF/CH3CN and then cooled to 0C. NEt3 (27.2 ml, 195 mmol) was added and then the acid chloride was added dropwise over 20 minutes. Stirred for 1 hour at 0C and then stored in freezer (-4C) overnight. Diluted with EtOAc and then washed with ¾0; added 0.5 N HCl to organic portion, stirred 5 minutes, basified with 1 N NaOH. Organic portion separated, washed with brine, dried (MgS04) and concentrated. Dissolved residue in EtOH (300 ml), added NEt3 (18.1 ml, 130 mmol) followed by portionwise addition of silver benzoate (3.72 g, 16.24 mmol, gas evolution). Heated to 80C for 10 minutes and then allowed to cool to ambient. The mixture was concentrated. Diluted with CH2Ci2, filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with hexanes to EtOAc to give 64-3 (8.05 g. 34.2%) as a colorless oil MS (ESI): m/z = 218.0 (MH+).

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 929022-76-4, 2-Chloro-4-fluoronicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BUNGARD, Christopher, James; PERKINS, James, J.; MANIKOWSKI, Jesse, J.; DE LEON, Pablo; MEISSNER, Robert, S.; WO2011/53574; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 2402-79-1, name is 2,3,5,6-Tetrachloropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2,3,5,6-Tetrachloropyridine

2,3,5,6-Tetrachloropyridine (0.1 mol), NaOH, TBAB and 60mL H2O were added to a 100 mL eggplant-shaped. The mixture was heated at 100 C for 8 hours, and monitored by TLC. Upon the reaction completion, the mixture was poured into icewater (100 mL) and was acidified to pH = 5-6. After filtration and extraction, F was obtained as white solid. The analytical data corresponded to the literature [15, 16].

The synthetic route of 2402-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Hao; Liu, Jian-Min; Shu, Lei; Wang, Man-Man; Yan, Yi-Le; Zhang, Da-Yong; Zhang, Jian-Qiu; Beilstein Journal of Organic Chemistry; vol. 16; (2020); p. 233 – 247;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6980-08-1, Adding some certain compound to certain chemical reactions, such as: 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine,molecular formula is C5H4ClN3O2, 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 6980-08-1.

4-Chloro-3-nitropyridin-2-amine (0.1 0 g, 0.58 mmol) was dissolved in dryacetonitrile (20 ml). To the stirred solution was then added N-bromosuccinimide (0.124g, 0.70 mmol), and the reaction mixture was heated at 80 C for 1 h. Volatiles wereremoved in vacuo and the residue purified by silica column chromatography (elution with25 dichloromethane) to provide the title compound as a pale brown powder (0.125 g, 85%).1 H-NMR (500 MHz, DMSO-d6) 7.35 (s, 2H, NH2), 8.41 (s, 1 H, 6-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. 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190320; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 942947-94-6, 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.942947-94-6, name is 5-Bromo-4-chloropyridin-2-amine, molecular formula is C5H4BrClN2, molecular weight is 207.4557, as common compound, the synthetic route is as follows.

General procedure: To 30 mL 98% H2SO4 was added portionwise 4,5-dichloropyridin-2-amine (1.0 g, 6.13 mmol) at -5 C. After the solid material was completely dissolved, 3.7 mL fuming HNO3 was added dropwise over 5 min maintaining internal temperature ?0 C. The mixture was allowed to warm to 50 C over 2 h, and then stirred for another 1 h at this temperature before poured onto 150 g crushed ice. The aqueous solution was basified to pH = 7.3 with ammonia and extracted with ethyl acetate. The combined extracts were dried, concentrated and purified by column chromatography to give 4,5-dichloro-3-nitropyridin-2-amine (0.80 g, 62.6%). 5.2.2.31 7-Bromo-8-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (31) To a solution of 2-amino-4-chloropyridine (1.28 g, 10.0 mmol) in anhydrous CH3CN (40 mL) was added portionwise N-bromosuccinimide (1.96 g, 11.0 mmol). The reaction mixture was stirred at room temperature for 24 h then poured into 100 mL ice-water and extracted with ethyl acetate. The combined extracts were washed with 1 M NaOH and brine, dried and evaporated. The residue was purified by column chromatography on silica gel to give 5-bromo-4-dichloropyridin-2-amine (1.53 g, 60.8%). Next steps followed the procedure of 30 and gave the title compound as white solid (63 mg, 12.5% over 3 steps).

Statistics shows that 942947-94-6 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-4-chloropyridin-2-amine.

Reference:
Article; Xie, Dongsheng; Lu, Jun; Xie, Jin; Cui, Junjun; Li, Teng-Fei; Wang, Yan-Chao; Chen, Yuan; Gong, Nian; Li, Xin-Yan; Fu, Lei; Wang, Yong-Xiang; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 19 – 32;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 874-80-6 ,Some common heterocyclic compound, 874-80-6, molecular formula is C9H14BrN, 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: Tributyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide [P44414][NTf2] (1); 1-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide [BMMIM][NTf2] (3); 1-butylpyridiniumbis(trifluoromethylsulfonyl)imide [BuPy][NTf2] (2); 1-allylpyridinium bis(trifluoromethylsulfonyl)imide[AllPy][NTf2] (5); 1-allyl-2,3-dimethylimidazoliumbis(trifluoromethylsulfonyl)imide [AlldiMIM][NTf2] (7)and 1,3-diallyl-2-methylimiidazolium bis(trifluoromethylsulfonyl)imide [diAllMIM][NTf2] (6) weresynthesized by metathesis reaction using the general procedure:Pyridinium or imidazolium halide (bromide or chloride) was dissolved in water and it wastransferred to a separator funnel with dichloromethane. Subsequently, 1.1 molar equivalent of LiNTf2(80% solution in water) was added and a separator funnel was shaken vigorously. After phaseseparation, the organic phase was washed twice with water, once with 5% water solution of LiNTf2,and this procedure was repeated until water phase was completely free of halide anion. To confirmabsence of chloride anion, acidic solution of silver nitrate was added to a sample of water phase. Noprecipitate of silver chloride indicated an absence of chloride anion. Subsequently, the organic phasewas separated, evaporated and dried under high vacuum (1 mbar) in 60 C for 24 h. The structure ofobtained salts were confirmed by 1H-NMR analysis.

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. 874-80-6, N-butylpyridinium bromide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zielinski, Witold; Kukawka, Rafal; Maciejewski, Hieronim; Smiglak, Marcin; Molecules; vol. 21; 9; (2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89167-19-1, 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 89167-19-1, name is 3-Bromo-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

3-Bromo-4-iodopyridine (2.2 g, 7.8 mmol), 2-Methoxyphenylboronic acid (1.3 g, 8.6 mmol), sodium carbonate (1.7 g, 15.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.22 g, 0.19 mmol) were charged and vessel evacuated and purged with nitrogen. Added nitrogen degassed 3:1 solution of dioxane and water (15 ml) and reaction heated to 100C for 2 hrs. Reaction was partitioned between EtOAc and water. The organics were washed with brine, dried and concentrated. The crude product was purified by flash column using a gradient of 100% Hexanes to 1:1 Hexanes and EtOAc to isolate the product as a glassy solid. LC-MS m z: 264 [M+l]

According to the analysis of related databases, 89167-19-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; SHAH, Shrenik, K.; KURUKULASURIYA, Ravi; FUNG, Selena; COLANDREA, Vincent, J.; SZEWCZYK, Jason, W.; WO2013/62887; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58584-86-4, 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. 58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, 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.

Ethyl 2,6-dichloropyridine-3-carboxylate (7.00 g, 31.81 mmol) and (6-isopropoxy-3-pyridyl)boronic acid (5.04 g, 27.85 mmol) were combined and dissolved in ethanol (50.40 mL) and toluene (50.40 mL). A suspension of sodium carbonate (10.12 g, 95.47 mmol) in water (10.08 mL) was added. Under nitrogen, tetrakis(triphenylphosphine)palladium (1.103 g, 0.9547 mmol) was added. The reaction mixture was allowed to warm to 80 C. and stirred for 2 h. The volatiles were removed under reduced pressure. The remaining solids were partitioned between water (75 mL) and ethyl acetate (75 mL). The organic layer was washed with saturated aqueous sodium chloride solution (1×75 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The material was subjected to silica gel column chromatography using a gradient from 100% hexanes to 5% ethyl acetate in hexanes. Ethyl 2-chloro-6-(6-isopropoxy-3-pyridyl)pyridine-3-carboxylate (3.95 g, 12.07 mmol, 43.33%) was obtained as a clear colorless oil. 1H NMR (400 MHz, DMSO) delta 8.91 (s, 1H), 8.37 (dd, J=8.7, 2.3 Hz, 1H), 8.30 (d, J=8.1 Hz, 1H), 8.10 (d, J=8.1 Hz, 1H), 6.89 (d, J=8.7 Hz, 1H), 5.34 (dt, J=12.3, 6.1 Hz, 1H), 4.36 (q, J=7.1 Hz, 2H), 2.51 (d, J=1.7 Hz, 1H), 1.42-1.30 (m, 9H). ESI-MS m/z calc. 320.09277. found 321.2 (M+1)+. Retention time: 0.72 minutes.

According to the analysis of related databases, 58584-86-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (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. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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. Application In Synthesis of 3-(Chloromethyl)pyridine hydrochloride

General procedure: DMF (5-10 mL/mmol). K2CO3 (10 equiv) was added and the suspensionstirred for 15 min. Then, 3-(chloromethyl) pyridiniumchloride (1.1 equiv) was added and the reaction mixture was stirredfor 48 h at room temperature. The suspension was diluted withH2O and extracted with EtOAc. The combined organic phases werewashed with H2O and brine, dried over magnesium sulfate and thesolvent was removed in vacuo. The crude products were purifiedby column chromatography [Cyclohexane/EtOAc, 3:1 4.2.2.3 tert-Butyl N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-pent-4-enoate (S)-Enantiomer, ((S)-15): Yield: 750 mg (55%), white solid. Mp 176-177 C. 1H NMR (300 MHz, CDCl3): delta 1.31 (s, 9H), 2.27 (ddd, 2JH,H = 14.7 Hz, 3JH,H = 8.0 Hz, 3JH,H = 6.9 Hz, 1H), 2.49 (dt, 3JH,H = 13.8 Hz, 3JH,H = 6.9 Hz, 1H), 3.86 (s, 3H), 4.49 (d, 2JH,H = 16.1 Hz, 1H), 4.51 (t, 3JH,H = 7.5 Hz, 1H), 4.69 (d, 2JH,H = 16.6 Hz, 1H), 4.89 (dd, 3JH,H = 17.1 Hz, 2JH,H = 1.5 Hz, 1H), 4.99 (dd, 3JH,H = 10.2 Hz, 2JH,H = 1.5 Hz, 1H), 5.60 (ddt, 3JH,H = 17.0 Hz, 3JH,H = 10.3 Hz, 3JH,H = 6.7 Hz, 1H), 6.94 (dm, 3JH,H = 9.0 Hz, 2H), 7.25 (dd, 3JH,H = 7.9 Hz, 3JH,H = 4.9 Hz, 1H), 7.73 (dm, 3JH,H = 9.0 Hz, 2H), 7.86 (d, 3JH,H = 7.9 Hz, 1H), 8.50 (d, 3JH,H = 4.0 Hz, 1H), 8.54 (d, 4JH,H = 1.7 Hz, 1H) ppm. 13C NMR (75 MHz, CDCl3): delta 27.8 (q), 35.5 (t), 46.6 (t), 55.6 (q), 60.2 (d), 82.3 (s), 114.1 (d), 118.4 (t), 123.3 (d), 129.6 (d), 131.5 (s), 133.0 (d), 133.7 (s), 136.6 (d), 148.5 (d), 149.0 (d), 163.0 (s), 169.3 (s) ppm. HRMS (ESI+): C22H28N2O5S+H+, calcd 433.1797, found: 433.1812; C22H28N2O5S + Na+, calcd 455.1617, found: 455.1630, (C22H28N2O5S)2+H+, calcd 865.3516, found: 865.3532; (C22H28N2O5S)2 + Na+, calcd 887.3336, found: 887.3345. Optical rotation (c 1.001, CHCl3): [alpha]58920 = -26.4, [alpha]57820 = -27.3, [alpha]54620 = -31.2, [alpha]43620 = -56.6, [alpha]36520 = -97.7.

With the rapid development of chemical substances, we look forward to future research findings about 6959-48-4.

Reference:
Article; Behrends, Malte; Wagner, Stefan; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Kumbhar, Sadhana; Waller, Mark; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3809 – 3818;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 69627-02-7, 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.69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, molecular weight is 151.19, as common compound, the synthetic route is as follows.

5.00 g of [3,2-b]pyridin-7-ol (33 mmol) and 50 g of phosphorus oxybromide (174 mmol) are put in a flask and heated at 1100C for 3h. The hot reaction mixture is poured into mixture of ice and 5N NaOH and extracted with CHC12, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane :AcOEt=3:l) to give 4.19 g of the title compound . Yield 59%. mass spectrum (m/e):215(M+l); IH-NMR(CDCl3): 8.55(d, IH, J=4.3Hz), 7.86(d, IH, J=5.7Hz), 7.69(d, IH, J=5.7Hz), 7.49(d, IH, J=4.3Hz) ppm.

Statistics shows that 69627-02-7 is playing an increasingly important role. we look forward to future research findings about Thieno[3,2-b]pyridin-7(4H)-one.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/107784; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem