Category: 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. 1086381-43-2, name is 2-Bromo-4-isopropylpyridine. A new synthetic method of this compound is introduced below., SDS of cas: 1086381-43-2

To a heat dried flask, phenylboronic acid (319.9 mg, 1.05 equiv., 2.624 mmol), potassium carbonate (1.036 g, 3 equiv., 7.5 mmol) and palladium(ii) acetate (56 mg, 0.1 equiv., 0.24990mmol%) were added. The flask was sealed and vacuumed and backfilled with nitrogen 3 times. Degassed ethanol (11.3 mL, 0.22 1 M) and water (2.8 mL, 0.885 M) were added, followed by 2-bromo-4-isopropyl-pyridine (500 mg, 2.4990 mmol), and the reaction was heated to 80C. The reaction was ran overnight, then was cooled to room temperature, was filtered through silica gel(isopropyl acetate eluting). The crude reaction was concentrated and purified by column chromatography to give a pale yellow oil (118.4 mg, 24% yield). 1H NMR (400 MHz, Chloroform-d) delta 8.58 (d, J = 5.2 Hz, 1H), 8.02 – 7.90 (m, 2H), 7.59- 7.54 (m, 1H), 7.50-7.34 (m, 4H), 7.08 (dd, J = 5.2, 1.6 Hz, 1H), 2.94 (hept, J = 6.9 Hz, 1H), 1.29 (d, J = 7.0 Hz, 6H).

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, 1086381-43-2, 2-Bromo-4-isopropylpyridine.

Reference:
Patent; GENENTECH, INC.; XENON PHARMACEUTICALS INC.; BERGERON, Phillipe; BURFORD, Kristen; CHOWDHURY, Sultan; DEHNHARDT, Christoph Martin; FOCKEN, Thilo; GRIMWOOD, Michael Edward; HASAN, Abid; LAI, Kwong Wah; LIU, Zhiguo; MCKERRALL, Steven; NGUYEN, Teresa Phuongtram; SAFINA, Brian; SUTHERLIN, Daniel; TAN, Wang Tao; (470 pag.)WO2017/58821; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75711-01-2, 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. 75711-01-2, name is 6-Chloro-5-methoxypyridin-3-amine, molecular formula is C6H7ClN2O, 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.

The 2-chloro-3-methoxy-5-aminopyridine (1.83 g, 11.58 mmol) was dissolved in EtOH (50 mL) and palladium acetate (2.0 g, 9.0 mmol), l,3-bis(diphenylphosphino)propane (3.5 g, 5.3 mmol), triethylamine (8.4 g, 83.38 mmol) were added sequentially and a stream of carbon monoxide was bubbled through the solution for 10 min. A balloon filled with CO was attached to the reaction flask and the mixture was stirred at 60 0C for 18 h. The mixture was cooled and diluted with ethyl acetate, filtered through a pad of Celite and evaporated. Purification using silica gel chromatography using hexane/ethyl acetate mixture provided 310 mg of product.

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 75711-01-2, 6-Chloro-5-methoxypyridin-3-amine.

Reference:
Patent; SCIOS, INC.; WO2006/112828; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1570-45-2 ,Some common heterocyclic compound, 1570-45-2, molecular formula is C8H9NO2, 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: To a stirred solution of 5 (0.22 mL, 2.0 mmol) in THF (10 mL) was added LiAlH4 (113 mg, 3.0 mmol) at 0 C, and the resulting mixture was refluxed for 7 h. After cooling, the reaction was quenched with 10% NaOH (aq), and the aqueous mixture was extracted with EtOAc (10 mL 3). The extracts were combined, dried over K2CO3, and evaporated to give alcohol, which was used directly in the next step. To a stirred solution of the alcohol obtained above in DMF (5 mL) was added NaH (60%, 88 mg, 2.2 mmol) at 0 C, and the reaction mixture was stirred at room temperature for 0.5 h. To the reaction mixture was added benzyl chloride (0.23 mL, 2.0 mmol) at 0 C, and the reaction mixture was stirred at room temperature for 2 h. The reactionwas quenched with H2O, and the aqueous mixture was extracted with EtOAc (10 mL x 3). The extracts were combined, dried over K2CO3, and evaporated to give residue, which was chromatographed on silica gel (15 g, hexane:acetone = 10:1) to give 6a (250 mg, 63%) as a pale yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1570-45-2, its application will become more common.

Reference:
Article; Ichihara, Yoshinori; Fujimura, Ryohei; Tsuneki, Hiroshi; Wada, Tsutomu; Okamoto, Kentaro; Gouda, Hiroaki; Hirono, Shuichi; Sugimoto, Kenji; Matsuya, Yuji; Sasaoka, Toshiyasu; Toyooka, Naoki; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 649 – 660;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206978-11-1, Adding some certain compound to certain chemical reactions, such as: 1206978-11-1, name is 2-Bromo-3-(trifluoromethoxy)pyridine,molecular formula is C6H3BrF3NO, 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 1206978-11-1.

To a stirred mixture of 2-bromo-3- (trifluoromethoxy) pyridine (300 mg, 1.24 nMol, 1 equiv) and Zn (CN) 2 (291.2 mg, 2.48 nMol, 2 equiv) in THF (15 mL) and H 2O (3 mL) , t-BuXantPhos-Pd-G3 (197.0 mg, 0.25 nMol, 0.2 equiv) and t-BuXantPhos (171.3 mg, 0.25 nMol, 0.2 equiv) under nitrogen atmosphere at RT. The resulted mixture was stirred for 2h at 80 under nitrogen atmosphere. The solvent was removed under reduced pressure. The residue was purified by Prep-TLC (CH 2Cl 2 /MeOH 20: 1) to afford 3- (trifluoromethoxy) pyridine-2-carbonitrile (200 mg, 85.76%) as a white solid. LCMS: m/z (ESI) , [M+H] + = 188.9.

According to the analysis of related databases, 1206978-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153747-97-8, 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 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of tert- Butyl 4-(5-bromo-2-pyridinyl)-l-piperazinecarboxylate (0.203 g, 0.593 mmol) and7V-({(55)- 3-[3-fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-l,3-oxazolidin-5- yl}methyl)acetamide (0.270 g, 0.714 mmol) in dmf (4 niL), EtOH (1.5 niL), toluene (2.5 mL) and K2CO3 (1 mL, 2 M, 2 mmol) was purged with nitrogen. PdCl2(dppf) (24 mg, 0.03 mmol) was added and the mixture was heated to 900C under nitrogen for 1 h, then partitioned between EtOAc and water. Column chromatography (EtOAc) gave the titled compound (0.21O g, 69%) as a white solid. APCI MS m/z 514 (M + H). 1H NMR (400 MHz, DMSO-J6) delta 8.32 (bs, IH), 8.27 (t, J= 5.9 Hz, IH), 7.75 (ddd, J- 8.9, 2.4, 1.7 Hz, IH), 7.53-7.60 (m, 2H), 7.38 (dd, J- 8.6, 2.2 Hz, IH), 6.94 (d, J= 8.9 Hz, IH), 4.72-4.79 (m, IH), 4.15 (t, J= 9.1 Hz, IH), 3.77 (dd, J = 9.2, 6.5 Hz, IH), 3.52-3.57 (m, 4H), 3.40-3.46 (m, 6H), 1.84 (s, 3H), 1.43 (s, 9H).

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 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; WO2009/120789; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 132521-70-1 , The common heterocyclic compound, 132521-70-1, name is 6-(4-Methylpiperazin-1-yl)nicotinic acid, molecular formula is C11H15N3O2, 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 6-(4-methylpiperazin- 1 -yl)nicotinicacid (150 mg, crude), tert-butyl 3-aminobiphenyl-4-ylcar-bamate (173 mg, 0.6 mmol) and EDCI (260 mg, 1.35 mmol)in pyridine (10 mE) was stirred at room temperature for overnight. The mixture was poured into water (20 mE), filtered to afford desired compound (300 mg, 89%) as a yellow solid.

The synthetic route of 132521-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Regenacy Pharmaceuticals, LLC; van Duzer, John H.; Mazitschek, Ralph; (123 pag.)US2018/141923; (2018); 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. 41668-13-7, name is 5-Bromo-6-hydroxynicotinic acid, molecular formula is C6H4BrNO3, 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. Safety of 5-Bromo-6-hydroxynicotinic acid

[0543] A solution of Example 117a (1 g, 4.58 mmol) and K2C03 (1.56 g, 13.76 mmol) in 10 mL of DMF, and was added Mel (0.7 mL, 11.46 mmol), the reaction was stirred at rt for 2.5 h. LCMS (BD01075-068) showed SM consumed, the mixture was poured into 30 mL water and stirred for 10 min. The mixture was extracted with EA (10 mL * 3). The combined organic phase was dried over MgS04, filtrated and the filtrate was concentrated under reduced pressure to get desired product (0.82 g, yield 73%) as yellow solid. LCMS [M+l] + = 246.0

With the rapid development of chemical substances, we look forward to future research findings about 41668-13-7.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 52311-50-9, 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 52311-50-9, name is 2-Chloro-4-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

6.01.22.02 1 – 4-ethoxy-pyridin-2-yl)-piperazine hydrochloride 860 mg piperazine was added to 350 mg 2-chloro-4-ethoxy-pyridine in 3.5 mL n-butanol. The reaction was stirred 1.5 days at 115C. The reaction was filtered and the filtrate was washed with water and evaporated. IN HCl was added to the residue and the precpipate was filtered to give 238 mg of the desired product. Rt: 0.3 min (method B), (M+H)+: 208

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 52311-50-9, 2-Chloro-4-ethoxypyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WO2013/107761; (2013); 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. 17117-17-8, name is 3-Bromo-5-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-5-ethoxypyridine

Under a nitrogen atmosphere, a mixture of 5-ethoxy-3-bromopyridine (1.20 g, 5.94 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.18 g, 5.94 mmol), palladium(II) acetate (13.5 mg, 0.06 mmol), tri-o-tolylphosphine (73.1 mg, 0.24 mmol), triethylamine (1.5 mL, 10.8 mmol), and anhydrous acetonitrile (3 mL) was stirred and heated under reflux at 80-85 C. for 28 h. The resulting mixture, containing beige solids, was cooled to ambient temperature, diluted with water (20 mL), and extracted with CHCl3 (3*20 mL). The combined light-yellow CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation, and vacuum dried producing a yellow oil (1.69 g). The crude product was purified by column chromatography on silica gel (100 g), eluding with ethyl acetate-hexane (1:1, v/v). Selected fractions containing the product (Rf 0.20) were combined, concentrated by rotary evaporation, and the residue was vacuum dried to give 0.67 g (35.2%) of a light-yellow oil. (4E)-N-Methyl-5-(5-ethoxy-3-pyridyl)-4-penten-2-amine

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, 17117-17-8, 3-Bromo-5-ethoxypyridine.

Reference:
Patent; Targacept, Inc.; US6979695; (2005); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89364-04-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 89364-04-5 as follows.

2.02 g (10.0 mmol) of 3-bromo-4-nitropyridine,2.20 g (11.0 mmol) of 4-bromophenylboronic acid,0.46 g (0.4 mmol) of tetraphenylphenylphosphine palladium,1.33 g (25 mmol) of Na2CO3 was dissolved in 60 mL of dioxane and 10 mL of water,110 reflux 12h, cooling,Poured into 80mL water,After extraction with 100 mL of ethyl acetate three times,Dried over anhydrous magnesium sulfate.The solvent was removed in vacuo,The solid was subjected to column chromatography,To give 2.1 g of product as a yellow solid (yield: 75%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89364-04-5, its application will become more common.

Reference:
Patent; Zhejiang University; He, Qinggang; Ren, Rong; Zhang, Kai; Zhang, Hong; Tian, Mei; (9 pag.)CN106588915; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem