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. 15862-34-7, name is 5-Bromo-2-hydroxy-3-nitropyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H3BrN2O3

Example 4N-(2-Methyl-3-(5-(5-(4-methylpiperazin-l-yl)pyridine-2-ylamino)-6-oxo-l,6- dihydropyridin-3-yl)phenyl)-4,5,6,7-tetrahydrobenzo[Z>]thiophene-2- carboxamide (19); 5-Bromo-2-methoxy-3-nitropyridine (15)[00197] In a 1 L, round-bottomed, single-necked flask equipped with a magnetic stirring bar was placed 5-bromo-3-nitropyridin-2-ol (50.0 g, 0.23 mol) in CHCl3 (500 mL) under nitrogen in the dark (wrapped in aluminum foil.) To this solution was added Ag2CO3 (75.5 g, 0.28 mol) and MeI (142.0 mL, 2.3 mol). After the mixture was stirred for 48 h at room temperature, it was filtered through a pad of Celite, washed with CH2Cl2, and concentrated. The crude mixture was purified by column chromatography (EtOAc:Hexane, 1:4) to give 24.0 g (45%) of 5-bromo-2- methoxy-3-nitropyridine (15) as a 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, 15862-34-7, 5-Bromo-2-hydroxy-3-nitropyridine.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; WO2008/33854; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73870-24-3, 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.73870-24-3, name is 4-(Bromomethyl)pyridine hydrobromide, molecular formula is C6H7Br2N, molecular weight is 252.93, as common compound, the synthetic route is as follows.

[00385] To a mixture of 53-1 (60 mg, 0.187 mmol, 1.00 eq) and 53-2 (85 mg, 0.336 mmol, 1.80 eq, HBr) in DMF (3 mL) was added K2C03 (100 mg, 0.723 mmol, 3.87 eq) in one portion at 25C. The mixture was stirred at 80 C for 3.5 h. LCMS showed the starting material was consumed completely and one main peak with the desired MS was detected. TLC showed one new spot was formed. The reaction mixture was extracted with EtOAc (40 mL) and washed with brine (30 mL*4). The organic layer was dried with anhydrous Na2S04, filtered, and concentrated under vacuum. The residue was purified by flash silica gel chromatography and then by prep-HPLC (basic condition) to provide the title compound (11.77 mg, 28.5 umol, 15.3% yield). LCMS (ESI): RT = 1.120 min, mass calc. for C20Hi5F3N6O 412.13, m/z found 413.0[M+H]+. 1HNMR (400MHz, DMSO-i_) 58.65- 8.55 (m, 3H), 8.01 (d, J=8.00 Hz, 1H), 7.47 – 7.37 (m, 2H), 7.33 (br d, J=5.20 Hz, 2H), 7.30 – 7.24 (m, 2H), 7.23- 7.17 (m, 2H), 7.06 (t, J=6.80 Hz, 1H), 6.12 (s, 2H).

Statistics shows that 73870-24-3 is playing an increasingly important role. we look forward to future research findings about 4-(Bromomethyl)pyridine hydrobromide.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1094679-27-2, Adding some certain compound to certain chemical reactions, such as: 1094679-27-2, name is 4-Ethynylpyridin-2-amine,molecular formula is C7H6N2, 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 1094679-27-2.

Compound 6 (510 mg, 1.33 mmol) ,tetrakis (triphenylphosphine)palladium(0) (23.1 mg, 0.02 mmol),copper iodide (13.3 mg, 0.07 mmol) and Compound 5a (157 mg, 1.33 mmol) It was dissolved in DMF (7 ml).This further added N,N-diisopropylethylamine (2 ml), was reacted for 14 hours at 70 C. in an oil bath.After the reaction, the solvent was distilled off, the resulting residue was adsorbed on a silica gel column, methanol – were eluted with a mixture of chloroform (1:50) to give Compound 7a (274 mg, 55%) .

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. 1094679-27-2, 4-Ethynylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIHON UNIVERSITY; SUZUKI, AZUSA; YOKOYAMA, SHOTA; SAITO, YOSHIO; (22 pag.)JP2015/221769; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6602-32-0 , The common heterocyclic compound, 6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, 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.

2-bromo-3-hydroxy-6-iodopyridine (1 1 -2)To a solution of 2-bromo-3-hydroxypyridine (11-1, 28 g, 161 mmol) in water (360 mL) was added K2CO3 (22.24 g, 161 mmol) and I2 (20.42 g, 80 mmol). The system was stirred for 1.5 h at ambient temperature, cooled to 0 C and then treated with concentrated HCl until solids precipitated from solution (pH~ 6.0). The solids were isolated by filtration and dried to give the title compound (11-2) as a brown solid. ESI+ MS C5H3BrINO: 299.8 found, 299.9 required.

The synthetic route of 6602-32-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/20642; (2009); 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. 1224464-97-4, name is Methyl 6-chloro-4-methylnicotinate, molecular formula is C8H8ClNO2, 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. Recommanded Product: 1224464-97-4

Methyl 6-chloro-4-methylnicotinate (150 mg, 0.81 mmol) and (3-bromo-2-chlorophenyl)boronic acid (228 mg, 0.97 mmol) dissolved in l,4-dioxane (6 mL) were treated with (1603) tetrakis(triphenylphosphine)palladium(0) (57 mg, 0.05 mmol) and potassium carbonate (224 mg, 1.62 mmol) dissolved in water. The reaction mixture was heated in the microwave at 110 C for lh. After cooling to room temperature, the reaction mixture was concentrated. The residue was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and purified by ISCO silica gel chromatography to give methyl 6-(3- bromo-2-chlorophenyl)-4-methylnicotinate.

With the rapid development of chemical substances, we look forward to future research findings about 1224464-97-4.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (300 pag.)WO2019/204609; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131747-45-0, 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 131747-45-0, name is (4-Bromopyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Under the protection of nitrogen,Add 3L DCM to the 5L three-neck bottle to cool down.240g of oxalyl chloride was added dropwise during cooling;At -60 C,295.6 g of Dimethyl sulfoxide (DMSO) was added dropwise to the reaction solution.Keep warm for 30min;At -60 C,237.5 g of Cpd 3 was added dropwise to the reaction solution.The reaction was carried out at -65 C for 1 hour;At this temperature, 3.5 eq of triethylamine (TEA) was added dropwise.After the solution was allowed to stand, the plate was measured.Through the column, the product 4-bromopyridine-2-carbaldehyde is obtained.(Cpd 4) 177.2g,The yield was 75%.

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 131747-45-0, (4-Bromopyridin-2-yl)methanol.

Reference:
Patent; Tianjin Quan He Cheng Science And Technology Co., Ltd.; Song Yanmin; Wan Jiaqiang; Li Weide; (11 pag.)CN108516953; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10592-27-5, 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. 10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine (5.00 g, 41.6 mmol) was dissolved in DMF (140 mL) and N-bromosuccinimide (8.89 g, 49.9 mmol) After that, the reaction was stirred at room temperature for 3 hours. A saturated aqueous solution of sodium hydrogencarbonate was added, and ethyl acetate was evaporated, washed with saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and purified by column chromatography (eluent: petroleum ether / ethyl acetate = 10:1 to 1:1)Intermediate 7 (3.60 g, 18.1 mmol,Yield 43%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Chengdu Xiandao Pharmaceutical Development Co., Ltd.; Li Jin; Wu Bo; Shang Siyun; Liao Wei; Lv Peng; Nong Yunhong; Chen Wei; (35 pag.)CN109705015; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19355-04-5, Adding some certain compound to certain chemical reactions, such as: 19355-04-5, name is 3-Methoxy-4-nitropyridine 1-oxide,molecular formula is C6H6N2O4, 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 19355-04-5.

EXAMPLE a) Preparation of 2-cyano-3-methoxy-4-nitropyridine A mixture of 12.5 g (12.5 moles) of the N-oxide of 3-methoxy-4-nitropyridine, 7.72 mL (1.1 eq.) of methyl sulphate and 70 mL of 1,2-dichloroethane is heated at 70 C. for 2.5 hours. It is allowed to cool and 70 mL of water are added. It is cooled in a salt and ice bath and, in portions, 7.55 g (2.1 moles) of sodium cyanide are added, controlling the temperature so as not to exceed 10 C. After 4 hours stirring, the reaction mixture is extracted with ethyl ether, the organic phase is washed with water, concentrated and the residue chromatographed (ethyl acetate/dichloromethane). There is obtained 7.06 g of a yellow oil (yield 53%).

According to the analysis of related databases, 19355-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nieto-Roman, Francisco; Vors, Jean-Pierre; Villier, Alain; Lachaise, Helene; Mousques, Adeline; Hartmann, Benoit; Hutin, Pierre; Molina, Jose Lorenzo; Muller, Benoit; US2003/191113; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56129-55-6, Adding some certain compound to certain chemical reactions, such as: 56129-55-6, name is 1-(Pyridin-3-yl)ethanamine,molecular formula is C7H10N2, 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 56129-55-6.

A sealed tube is charged with 7-chloro-5-(1 -methyl- 7 – -indol-6-yl)-quinoxaline (60.00 mg; 0.20 mmol; 1.0 eqr.) (Intermediate 4), 1-pyridin-3-yl-ethylamine (0.05 ml0.41 mmol; 2.0 eqf.), NaOtBu (58.77 mg; 0.61 mmol; 3.00 eqf.) and toluene (2.0 ml_). RM is purged with argon and then BINAP (25.39 mg; 0.04 mmol; 0.20 eqf.) and Pd2(dba)3 (18.67 mg; 0.02 mmol; 0.10 eq.) are added. RM is sealed and heated at 1 10C for 16 h. After this time, the mixture is filtered through a Celite pad and the filtrate is diluted with EtOAc and extracted with water. Combined organic phases are washed with brine, dried over Na2S04. Solvent is evaporated and the residue is purified by FCC (hexane/EtOAc; gradient). [8-(1 -Methyl- 7H-indol-6-yl)-quinoxalin-6-yl]-(1 – pyridin-3-yl-ethyl)-amine is obtained as a yellow powder (60.00 mg; yield 79%; 97% by HPLC).

According to the analysis of related databases, 56129-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6221-01-8, 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. 6221-01-8, name is Pyridine-2,5-dicarbaldehyde. A new synthetic method of this compound is introduced below.

General procedure: To a stirred solution of 2,5-pyridinedicarboxaldehyde(0.37 mmol) in 5 mL EtOH was added the indole (1.85 mmol) andI2 (0.15 mmol). The resulting mixture was stirred at reflux for 6 hcooled and treated with aqueous Na2S2O3. The combined organiclayers obtained by extraction with EA (3 30 mL) were washedwith H2O (2 10 mL) and brine (2 10 mL), dried over MgSO4 and concentrated under reduced pressure to give a residue, which wassubjected to flash column chromatography, followed by normalphaseHPLC to afford the pure product. 4.3.2 3,3′,3″,3?-(Pyridine-2,5-diylbis(methanetriyl))tetrakis(1H-indole) (3a) Yield 50% (white powder), mp 164-165 C, 1H NMR (400 MHz, DMSO-d6): delta 10.85 (s, 2H, NH), 10.81 (s, 2H, NH), 8.51 (s, 1H, ArH), 7.59 (d, J = 8.4 Hz, 1H, ArH), 7.35-7.25 (m, 9H, ArH), 7.05-7.00 (m, 4H, ArH), 6.90 (s, 2H, ArH), 6.87-6.83 (m, 6H, ArH), 5.89 (s, 1H, CH), 5.86 (s, 1H, CH). 13C NMR (100 MHz, DMSO-d6): delta 162.48, 149.53, 138.42, 137.51, 137.36, 136.97, 127.65, 127.36, 124.49, 124.42, 122.88, 121.90, 121.74, 119.92, 119.20, 119.12, 118.32, 118.05, 112.45, 112.35, 43.21, 37.74. HRMS calcd for C39H30N5 (M + H)+, 568.2501; found, 568.2500.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6221-01-8, its application will become more common.

Reference:
Article; Fu, Chih-Wei; Hsieh, Yun-Jung; Chang, Tzu Ting; Chen, Chia-Ling; Yang, Cheng-Yu; Liao, Anne; Hsiao, Pei-Wen; Li, Wen-Shan; European Journal of Medicinal Chemistry; vol. 104; (2015); p. 165 – 176;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem