Category: pyridine-derivatives

Electric Literature of 133081-24-0, 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.133081-24-0, name is 6-Hydrazinylnicotinic acid, molecular formula is C6H7N3O2, molecular weight is 153.14, as common compound, the synthetic route is as follows.

General procedure: A 0.5M solution of 2-chloropyridine-5-carboxylic acid (15 mmol) was treated with hydrazine hydrate (150 mmol, added at once) and heated at reflux for 72 h. The suspension was concentrated to dryness. The residue was dissolved in water and acidified (pH = 3) with acetic acid. The precipitate of 2-hydrazinopyridine-5-carboxylic acid that formed in 15 min was filtered off, washed with water and air-dried. It was dissolved in the respective aliphatic carboxylic acid and the solution (0.5M) was heated at reflux for 48 h. Upon cooling to room temperature, the volatiles were removed in vacuo and the residue was triturated with 1M aqueous sodium bicarbonate. The precipitate thus formed was filtered off, washed with water and air dried. The resulting 1,2,4-triazolo[4,3-a]pyridine 12 was dissolved in methanol (0.25M and was hydrogenated over Pd(OH)2 catalyst (0.1 equiv.) at 100 atm and 100 C over 24 hours. The mixture was filtered while still hot and concentrated in vacuo. The residue was crystallized from isopropyl alcohol to provide analytically pure carboxylic acids 11a-d.

Statistics shows that 133081-24-0 is playing an increasingly important role. we look forward to future research findings about 6-Hydrazinylnicotinic acid.

Reference:
Article; Mishchuk, Alexander; Shtil, Natalia; Poberezhnyk, Mykola; Nazarenko, Konstiantyn; Savchenko, Timur; Tolmachev, Andrey; Krasavin, Mikhail; Tetrahedron Letters; vol. 57; 9; (2016); p. 1056 – 1059;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

A mixture of 2-bromo-3,5-dichloropyridine (5.672 g, 25 mmol), sodium iodide (11241.7 mg, 75 mmol) and chlorotrimethylsilane (2716 mg, 25 mmol) in MeCN (50 mL) was heated under reflux for 45 min. The reaction mixture was then poured into a 2.0 M aqueous solution of sodium hydroxide (10 mL) and extracted with diethyl ether (20 mL x 3). The combined organic layers were washed with brine and evaporated to afford crude product, which was purified by biotage (EtOAc/PE=l% ~ 10%, ISCO 40 g, 25 mL/min, normal phase silica gel, uv 254) to afford the target compound 3,5- dichloro-2-iodopyridine (3800 mg, 55.5 % yield) as a white solid. 1H NMR (400 MHz, MeOD) delta 8.35 (t, J= 4.5 Hz, 1H), 8.01 (d, J= 2.3 Hz, 1H). GC-MS m/z calcd for [C5H2C12IN]: 272.9; found: 273.0.

Statistics shows that 14482-51-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-3,5-dichloropyridine.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588729-99-1, Adding some certain compound to certain chemical reactions, such as: 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine,molecular formula is C5H4BrClN2, 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 588729-99-1.

N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide 5-Bromo-2-chloro-3-pyridinamine [commercially available] (10 g, 48.2 mmol) was dissolved in pyridine (75 ml) and methanesulfonyl chloride (7.46 ml, 96 mmol) added, and the mixture stirred overnight. Further methanesulfonyl chloride (2.1 ml) was added and the reaction stirred at room temperature for 5 h. A further portion of methanesulfonyl chloride (2.1 ml) was added and the mixture stirred at room temperature overnight. The pH was adjusted to ?pH6 by the addition of 2M hydrochloric acid. The mixture was then extracted with dichloromethane (2*150 ml) the combined organic layers were dried using a hydrophobic frit and the solvent removed in vacuo. The residue was suspended in methanol (200 ml) and 2M sodium hydroxide (50 ml) added. The mixture was stirred for 1 h and then the solvent removed in vacuo. The residue was dissolved in water (250 ml) and extracted with dichloromethane (150 ml). The aqueous layer was then acidified and the resulting precipitate collected by filtration. The solid was air dried overnight to give the title compound as an off white solid (13.45 g).

According to the analysis of related databases, 588729-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 62733-99-7, Methyl 3-hydroxypicolinate, 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, 62733-99-7, blongs to pyridine-derivatives compound. SDS of cas: 62733-99-7

To a solution of 3-hydroxy-pyridine-2-carboxylic acid methyl ester (200 mg, 1.3 mmol) in N,N-dimethylformamide (2.0 ml) was added at 22 0C sodium hydride (55% in oil, 64 mg) and stirring was continued until gas evolution ceased. The suspension was cooled to 0 0C and treated with trifiuoro ethyl trifiuormethanesulfonate (728 mg) and stirring was continued at 22 0C for 2 hours. The mixture was partitioned between saturated sodium hydrogen-carbonate solution and ethyl acetate, and the organic layer was dried and evaporated. The residue was purified by chromatography on silica using n-heptane and ethyl acetate (3:1) as the eluent to give 3-(2,2,2- trifluoro-ethoxy)-pyridme-2-carboxylic acid methyl ester as a pale green oil. Mass (calculated) C9H8F3NO3 [235.16]; (found) [M+H]+ = 236

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62733-99-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; ANDREINI, Matteo; BANNER, David; GUBA, Wolfgang; HILPERT, Hans; MAUSER, Harald; MAYWEG, Alexander, V.; NARQUIZIAN, Robert; POWER, Eoin; ROGERS-EVANS, Mark; TRAVAGLI, Massimiliano; VALACCHI, Michela; WOLTERING, Thomas; WOSTL, Wolfgang; WO2011/20806; (2011); A1;,
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

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

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

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

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 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