Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 73781-91-6, Methyl 6-chloronicotinate, 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, Application In Synthesis of Methyl 6-chloronicotinate, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 6-chloronicotinate

Step e: 6-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester To a suspension of sodium hydride (55% dispersion in mineral oil, 852 mg, 20 mmol) in THF (27 mL) was added a solution of [3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (103 mg, 0.55 mmol) (3.68 g, 18 mmol) in THF (54 mL) at 0 C. and the reaction mixture warmed to room temperature over 30 min. Then a solution of methyl 6-chloronicotinate (3.35 g, 20 mmol) in THF (1.5 mL) was added dropwise at 0 C. and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and brine and then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=7:3) afforded the title compound (81 mg, 47%) which was obtained as a light yellow solid. MS: m/e=343.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73781-91-6, Methyl 6-chloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; Dott, Pascal; Grassmann, Olaf; Kammerer, Michael; Manns, Joachim; Schwitter, Urs; Thomas, Andrew; Wyttenbach, Nicole; US2013/172329; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7356-60-7, 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 7356-60-7, name is Nicotinimidamide hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

Compound F (9.15 g, 25 mmole),3-pyridinecarboxamidine hydrochloride (3.94g, 25mmole)And potassium hydroxide (1.68g, 30mmole) into a 500mL double-neck round bottom flask,Add 150 mL of ethanol and heat to reflux.After 3 hours of reaction,Leave to warm to room temperature, filter, wash the solid with ethanol,There was obtained 8.45 g of compound G as a white solid,The yield was 72.4%.

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 7356-60-7, Nicotinimidamide hydrochloride.

Reference:
Patent; E-RAY OPTOELECTRONICS TECHNOLOGY CO., LTD.; CHANGZHOU TRONLY E-RAY OPTOELECTRONICS MATERIAL CO., LTD.; HUANG, HEH LUNG; CHAO, TENG CHIH; GUO, HUANG MING; LIN, CHI JEN; CHANG, MIN JONG; (48 pag.)TWI672298; (2019); B;,
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. 118399-86-3, name is 6-Bromo-2-methylpyridin-3-ol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 118399-86-3

To a solution of (lR,3s,5S)-tert-butyl 3-((ls,4S)-4-hydroxycyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (500 mg, 1.536 mmol), 6-bromo-2-methylpyridin-3-ol (0.347 g, 1.844 mmol), and triphenylphosphine (0.484 g, 1.844 mmol) in THF (5 mL) at room temperature under nitrogen was added triethylamine (0.257 mL, 1.844 mmol), followed by dropwise addition of diisopropyl diazene-l,2-dicarboxylate (0.364 mL, 1.844 mmol). After 18 h stirring at room temperature, the mixture was concentrated in vacuo and purified by preparative HPLC. Pure fractions were combined, neutralized with saturated sodium bicarbonate (aq), and evaporated MeCN to form a solid. The solid was collected by vacuum filtration, washed with water, and dried under reduced pressure to give the title compound (175.1 mg, 0.353 mmol, 23.0%) as a white solid. Exact mass calculated for C24H35BrN204: 494.2, found: LCMS m/z = 495.6 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.37-1.45 (m, 2H), 1.47 (s, 9H), 1.50-1.71 (m, 6H), 1.84-1.99 (m, 6H), 2.00-2.11 (m, 2H), 2.42 (s, 3H), 3.44-3.55 (m, 1H), 3.76-3.88 (m, 1H), 4.12-4.35 (m, 3H), 6.97 (d, = 8.6 Hz, 1H), 7.21 (d, = 8.6 Hz, 1H).

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, 118399-86-3, 6-Bromo-2-methylpyridin-3-ol.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 108-48-5, 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.108-48-5, name is 2,6-Dimethylpyridine, molecular formula is C7H9N, molecular weight is 107.1531, as common compound, the synthetic route is as follows.

General procedure: A mixture of 2-methyl quinoline (1 mmol), aryl aldehyde (1 mmol), Ca (OTf)2 (5 mol%) andBu4NPF6 (2 mol%) were heated at 130 oC under neat condition for 4-5 h. After completion of the reaction (monitored by TLC), reaction mixture was brought to roomtemperature, diluted with dichloromethane, absorbed on silica gel and purified by column chromatography using petroleum ether/ethyl acetate to give the desired product.

Statistics shows that 108-48-5 is playing an increasingly important role. we look forward to future research findings about 2,6-Dimethylpyridine.

Reference:
Article; Yaragorla, Srinivasarao; Singh, Garima; Dada, Ravikrishna; Tetrahedron Letters; vol. 56; 43; (2015); p. 5924 – 5929;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5337-79-1, 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. 5337-79-1, name is 3-(Pyridin-4-yl)acrylic acid, molecular formula is C8H7NO2, 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.

EXAMPLE 33; (alphaR,gammaS,2S)-N-((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)-gamma-hydroxy4-[(5-phenyl-2-furanyl)methyl]-alpha-(4-pyridinylmethyl)-2-[[(2,2,2-trifluoroethyl)amino]carbonyl]-1-piperazinepentanamide; To a solution of 3-(4-pyridyl)-acrylic acid (25.0 g, 168 mmol) in 1:1 ethanol:THF (250 mL) was added 10% Pd(0)/C (2.50 g). The reaction vessel was placed under 110 psi of H2 until 1.0 equivalent of H2 had been consumed as indicated by a pressure drop in the reaction vessel. The mixture was then diluted with 1 L of hot methanol and filtered through celite, rinsing with hot methanol. The liquid obtained was concentrated in vacuo, affording 11.0 g (43% of 3-(4-pyridyl)-propionic acid. This material was dissolved in DMF (300 mL), and to this solution was added the aminochromanol intermediate from Example 1, Step L (12.0 g, 72.5 mmol), HOBT (11.7 g, 87.0 mmol), di-iso-propylethylamine (27.8 mL, 159 mmol) and HBTU (27.5 g, 72.5 mmol). After 2 hours at ambient temperature, the reaction was quenched with 0.5 N aqueous NaHCO3 (500 mL) and diluted with ethyl acetate (1 L). The organic layer was washed with 0.5 N NaHCO3 (300 mL×3), brine (300 mL), dried (MgSO4), and concentrated in vacuo, affording 13.2 g (61%) of the amide as a white solid. A portion of this material (2.27 g, 7.61 mmol) was dissolved in dichloromethane (100 mL), and 2-methoxypropene (3.64 mL, 38 mmol) was added, followed by camphorsulfonic acid (1.20 g, 5.17 mmol). After 3 hours at ambient temperature the reaction was quenched by the addition of 1.4 mL of triethylamine, and concentrated in vacuo. Purification by flash chromatography (3% methanol in ethyl acetate) afforded the title compound as a clear oil.

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 5337-79-1, 3-(Pyridin-4-yl)acrylic acid.

Reference:
Patent; Merck & Co., Inc.; US6642237; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-98-0, 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.13534-98-0, name is 4-Amino-3-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.

General procedure: Step 1: A vial equipped with a magnetic stir bar was charged with the orthohaloaminopyridineand BrettPhos G1 precatalyst (6 mol %). The vial was sealedwith a teflon screw cap, and evacuated and backfilled with argon three times. Theamine (1 to 1.5 mol eq) was added via syringe, followed by LiHMDS solution (1M in THF, 2.5 mol eq). Amines that were solid at room temperature were addedwith the catalyst. The reaction mixture was stirred at 40 C for 4-18 h, until LC/MSindicated complete conversion of the starting material. The mixture was cooled toroom temperature, diluted with dichloromethane, and poured into water. Theorganic phase was separated and the aqueous phase was extracted twice more withdichloromethane. The combined organic phases were dried over Na2SO4. Thesolvent was removed under reduced pressure.

The chemical industry reduces the impact on the environment during synthesis 13534-98-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Chaomin; Chen, Lily; Steinhuebel, Dietrich; Goodman, Andrew; Tetrahedron Letters; vol. 57; 25; (2016); p. 2708 – 2712;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 754214-42-1, 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 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, Product Details of 754214-42-1, blongs to pyridine-derivatives compound. Product Details of 754214-42-1

A suspension of 1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (250 mg, 1.5 mmol) in N,N-dimethylformamide (5 mL) was warmed to 40 C. N-chlorosuccinimide (243 mg, 1.62 mmol) was added and the mixture was stirred at 55 C. for 5 hours. The reaction was cooled to room temperature and left stirring for 2 days. The mixture was diluted with water (20 mL) and stirred overnight. The resulting solid was collected by filtration and dried to give the title compound (161 mg, 55%). +ESI (M+H) 197.1; 1H NMR (400 MHz, DMSO-d6, delta): 13.08 (br. s., 1H), 12.39 (br. s., 1H), 8.86 (d, J=1.8 Hz, 1H), 8.40 (d, J=1.2 Hz, 1H), 7.84 (d, J=2.5 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,754214-42-1, 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US2012/108619; (2012); 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. 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, the common compound, a new synthetic route is introduced below. Safety of Methyl 6-chloro-5-nitronicotinate

Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl 2-(benzylamino)acetate (6.0 g, 31.05 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30percent gradient, ethyl acetate in hexanes) to yield the title compound (3.10 g, 90percent yield) as a yellow oil. [M+H] calc’d for C18H19N3O6, 374; found, 374.

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2010/190763; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 30766-11-1 , The common heterocyclic compound, 30766-11-1, name is 5-Bromopicolinic acid, molecular formula is C6H4BrNO2, 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.

To a mixture of 5-bromopyridine-2-carboxylic acid (2.5 g, 12 mmol) in methylene chloride (10.0 mL) was added oxalyl chloride (1.6 mL, 18 mmol), followed by N,N-dimethylformamide (0.020 mL, 0.26 mmol). After stirred at RT for 2 h, the mixture was evaporated under reduced pressure. The residue was the acid chloride which was used directly in next step reaction.

The synthetic route of 30766-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhuo, Jincong; Qian, Ding-Quan; Yao, Wenqing; US2007/129345; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10366-35-5 ,Some common heterocyclic compound, 10366-35-5, molecular formula is C6H5ClN2O, 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.

Example 3 2-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]nicotinamide Operation was carried out in a manner similar to the one described in Example 2, using 1.6 g of 2-chloronicotinamide, 3.2 g of 1-(2,3-dihydroxypropyl)piperazine and 30 ml ethanol and refluxing overnight. Column purification of the residue gave 1 g of 2-[4-(2,3-dihydroxypropyl)piperazin-1-yl]nicotinamide, which, recrystallized from acetone, melted at 140-142C.

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. 10366-35-5, 2-Chloronicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOMPE’ FARMACEUTICI S.p.A.; EP230402; (1993); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem