Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 74115-13-2, 5-Bromo-3-pyridinol, 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, 74115-13-2, blongs to pyridine-derivatives compound. Formula: C5H4BrNO

A mixture of 3-bromo-5-hydroxypyridine (At°rich, Buchs, Switzerland, 611 mg, 3.51 mmol), potassium carbonate (971 mg, 7.02 mmol) and 2-bromoethyl methyl ether (537 mg, 3.86 mmol) in 30 ml DMF was stirred for 14 h at rt and for 2 h at 80C The reaction mixture was quenched with water and extracted with EtOAc (2x). The organic layers were washed with brine (3x), dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (dichloromethane/MeOH 0% to 3%) to give the title compound as an oil (HPLC- tkappa 2.38 min (Method A), M+H = 232, 234 MS-ES)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74115-13-2, its application will become more common.

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

Related Products of 66572-56-3, 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 66572-56-3, name is 2-Bromoisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

2-Bromoisonicotinic acid (2.02 g, 10 mmol) was dissolved in DMF (80 mL) under argon. Pd(PPh3)4 (0.6 g, 0.52 mmol) was added, and the reaction mixture was stirred at room temperature for 15 min. Na2CO3 (aq. 2N, 40 mL) was then added, followed by the addition of phenylboronic acid (1.67 g, 13.7 mmol). The reaction mixture was heated at 95C (18 h), cooled to room temperature and filtered through a celite pad. Water (80 mL) was added, and the mixture was acidified with HCl (2 N) to pH = 4. The precipitate was collected via filtration and rinsed with water (2 x 7 mL). The crude product was recrystallized from 2-methoxylethanol to give 2- phenylisonicotinic acid as a grey solid (1.2 g). 1HNMR (DMSO-d6, 400 MHz): delta 7.51 (m, 3H), 7.78 (d, J=4.8 Hz, 1H), 8.13 (t, J=1.6 Hz, 2H), 8.29 (s, 1H), 8.85 (d, j=4.8 Hz, 1H), 13.73 (bs, 1H).

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 66572-56-3, 2-Bromoisonicotinic acid.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2008/156869; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 148038-83-9, 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.148038-83-9, name is 6-Bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one, molecular formula is C6H4BrN3O, molecular weight is 214.02, as common compound, the synthetic route is as follows.

A. 6-Bromo-2-chloro-3H-imidazo[4,5-b]pyridine Reflux 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (5 g) for 14 h in POCl3 (50 mL). Evaporate the solvent in vacuo, then carefully neutralize with saturated NaHCO3, and extract with EtOAc. Dry over Na2SO4, concentrate under vacuum, and purify by flash chromatography (1:1 hexanes/EtOAc) to obtain 6-bromo-2-chloro-3H-imidazo[4,5-b]pyridine.

The chemical industry reduces the impact on the environment during synthesis 148038-83-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROGEN CORPORATION; US2003/36652; (2003); 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. 38496-18-3, name is 2,6-Dichloronicotinic acid, the common compound, a new synthetic route is introduced below. SDS of cas: 38496-18-3

(a) 19.1 g (0.1 mole) of 2,6-dichloronicotinic acid [Guthzeit and Laska, J. pr. Ch. 58 [2], 425 (1898)] are suspended in 250 ml of methanol and, while stirring and cooling with ice, hydrogen chloride gas is introduced until the mixture is saturated. The reaction mixture is allowed to stand for 48 hours at room temperature and subsequently heated for 3 hours to reflux temperature. It is then evaporated to dryness in a high vacuum at 40 C and the residue is dried in a high vacuum at 40 C. The brown crystalline product is recrystallized from ether-pentane to yield methyl 2,6-dichloronicotinate with a melting point of 53-54 C.

The synthetic route of 38496-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4089960; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16867-03-1, 2-Amino-3-hydroxypyridine, 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, Formula: C5H6N2O, blongs to pyridine-derivatives compound. Formula: C5H6N2O

EXAMPLE 59 2-Ethyloxazolo [4,5-b]pyridine A mixture of 4.4 g. of 2-amino-3-hydroxypyridine, 10.4 g. of propionic anhydride and 15 g. of polyphosphoric acid was heated at 168 C. for 15 minutes. The reaction mixture was cooled slightly and poured into ice water and stirred until the polyphosphoric acid had decomposed. The solution was made alkaline with solid sodium bicarbonate and extracted with 150 ml. of methylene chloride. The dried methylene chloride solution was concentrated to dryness and the residue was dissolved in ether and filtered through aluminum oxide. From the ether filtrate there was obtained 1.2 g. of 2-ethyloxazolo[4,5-b]pyridine, m.p. 52-53 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16867-03-1, 2-Amino-3-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US4038396; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 884495-03-8, 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. 884495-03-8, name is 3-Amino-2-bromo-5-fluoropyridine. A new synthetic method of this compound is introduced below.

Ethynyltrimethylsilane (0.82 mL, 6.3 mmol) was added dropwise to a stirred mixture of 2-bromo-5-fluoropyridin-3-amine (1.0 g, 5.23 mmol), Pd(PPh3)2Cl2 (0.18 g, 0.26 mmol) and Cul (50 mg, 0.26 mmol) in triethylamine (15 mL) at 0C. The reaction was stirred for 4 h at rt under nitrogen. The mixture was concentrated under reduce pressure. The residue was purified by silica gel column chromatography (PE/EA, from 20/1 tolO/1) to give compound 23 (0.8 g, 73% yield). LC-MS: 209.16 (M+H), Ci0Hi3FN2Si. 1H NMR (CDC13, 400 MHz) 0: 7.83 (s, 1H), 6.75-6.72 (m, 1H), 4.40 (br, 2H), 0.28 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884495-03-8, 3-Amino-2-bromo-5-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; AKARNA THERAPEUTICS, LTD.; MOHAN, Raju; PRATT, Benjamin, Anthony; (297 pag.)WO2016/103037; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1121-76-2 , The common heterocyclic compound, 1121-76-2, name is 4-Chloropyridine 1-oxide, molecular formula is C5H4ClNO, 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.

A mixture of 4-chloropyridine, 1 -oxide (0.0025 mol), Pd2(dba)3 (catalytic quantity), Xantphos (catalytic quantity) and Cs2CO3 (0.973 g) in dioxane (5ml) was degassed by applying alternating N2 atmosphere and vacuum. Intermediate (70) (0.0023 mol) in dioxane (15ml) was added under N2-atmosphere. The reaction mixture was stirred at 1000C for 2 hours. The mixture was extracted (DCM/H2O), dried, filtered and evaporated. The residue was used crude, yielding intermediate (71).

The synthetic route of 1121-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2008/3665; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16179-97-8 ,Some common heterocyclic compound, 16179-97-8, molecular formula is C7H8ClNO2, 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.

A suspension of 2-pyridineacetic acid hydrochloride (Aldrich; 1.74 g, 10 mmol) and carbonyl diimidazole (1.95 g, 12 mmol) in anhydrous THF (20 mL) was stirred at rt for 1 h. To the mixture was added solid 4-chloroaniline (1.28 g, 10 mmol). After stirring overnight, the solvent was removed and the residue was partitioned between water and EtOAc. The organic layer was dried over Na2SO4 and evaporated to dryness. The crude product was recrystallized from 20 mL of toluene affording 1.5 g (60%) of the amide as a solid. TOF MS ES+ m/z 247 (MH+), 269 (M+Na+).

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. 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hogenkamp, Derk J.; Johnstone, Timothy B.C.; Gee, Kelvin W.; US2006/293329; (2006); A1;,
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. 181123-11-5, name is 5-Chloro-2-cyano-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H2ClN3O2

Step 1: 3-Amino-5-chloropicolinamide To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta 7.88 (br. s, 1H), delta 7.73 (s, 1H), delta 7.39 (br. s, 1H), delta 7.23 (s, 1H), delta 7.06 (br. s, 2H). LC/MS (ESI+) m/z=172 (M+H).

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, 181123-11-5, 5-Chloro-2-cyano-3-nitropyridine.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69142-64-9, 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 69142-64-9, name is Ethyl 6-aminopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Step 2. Preparation of ethyl 6-(tert-butoxycarbonylamino)picolinate (79):To a solution of ethyl 6-aminopicolinate 78 (5.5 g, 33 mmol) in £-BuOH (120 mL) and acetone (40 mL) was added 4-dimethylaminopyridine (0.08g, 0.66 mmol) and di-tert-butyl dicarbonate (10.8 g, 49.5 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed by concentration under reduced pressure and a mixture of hexane/dichloromethane (180 mL, 3:1) was added. The resulting mixture was cooled to -20 0C for 2 h. The resulting solids were collected by filtration and dried to afford 79 (11.O g, 91 % yield).

According to the analysis of related databases, 69142-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; OALMANN, Christopher; PERNI, Robert, B.; VU, Chi, B.; WO2010/37127; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem