Category: pyridine-derivatives

Synthetic Route of 1095823-39-4, 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 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A 20 mL vial was charged with compound A.5 (191.8 mg, 0.0006561 mol), methylene chloride (3.0 mL), a 2.0 M solution of oxalyl chloride in methylene chloride (390 muL) and DMF (10.0 muL, 0.000129 mol). The reaction mixture was stirred for 15 minutes at rt, then concentrated in vacuo and the resultant residue was taken up in acetonitrile (3.0 mL). To this solution was added a solution of compound A.6 (129 mg, 0.000656 mol) and pyridine (0.5 mL, 0.006 mol) in acetonitrile (1.5 mL). The reaction mixture was stirred at RT overnight. The solvent was removed under reduced pressure, and the residue was purified by combiflash (0-30% EtOAc/CH2Cl2) to give compound A.7 in 49% yield. LCMS: m/z 471 [M+1]+.

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 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 940943-37-3, S-(2-(6-(4-(3-(Dimethylamino)propoxy)phenylsulfonamido)pyridin-3-yl)-2-oxoethyl) ethanethioate, 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 940943-37-3, blongs to pyridine-derivatives compound. Product Details of 940943-37-3

[0200] A 1 : 1 mixture of Compound 1 (0.3006 g) and L-malic acid (0.0893 g) was dissolved in 10 mL methanol at 70 0C. Oil formed upon cooling to ambient temperature. Seeds (Malate A) were added and the sample was stirred, overnight, at ambient temperature. Light yellow solids were observed and obtained by vacuum filtration. The solids were left to air dry overnight (0.2803 g; yield 72%, based on unsolvated weight).

The synthetic route of 940943-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2008/73733; (2008); 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. 52311-50-9, name is 2-Chloro-4-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-4-ethoxypyridine

A solution of [(2R,5R)-5-hydroxy-2-methylpiperidin-l-yl][2-(2H- 1,2,3 -triazol-2- yl)phenyl]methanone (0.025 g, 0.087 mmol) in DMF (1 mL) was treated with sodium hydride (3.1 mg, 0.131 mmol). After stirring ~20 minutes, 2-chloro-4-ethoxypyridine (16.5 g, 0.105 mmol) was added and the reaction was heated to 50 C overnight. Additional sodium hydride (1.6 mg, 0.065 mmol) was added, and the reaction was heated to 80 C for 4 h, then quenched with saturated aqueous ammonium chloride and diluted with water. The mixture was extracted 3x with ethyl acetate and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-3% methanol in dichloromethane) to provide the title compound. FIRMS m/z (Mu+Eta) 408.2016 found, 408.2030 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/137883; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1206775-52-1 ,Some common heterocyclic compound, 1206775-52-1, molecular formula is C7H6BrNO2, 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) Tetrakistriphenylphosphine palladium (403 mg), phenylboronic acid (510 mg) and a 2 M sodium carbonate solution (3.5 mL) were sequentially added to a solution of 5-bromo-6-methoxypyridine-2-carbaldehyde (753 mg) in 1,2-dimethoxyethane (23 mL) in a nitrogen atmosphere, and the mixture was stirred at 80 C. for three hours. Water was added to the reaction solution at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1?1:1) and further purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to give 6-methoxy-5-phenylpyridine-2-carbaldehyde (445 mg, 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206775-52-1, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18699-87-1 ,Some common heterocyclic compound, 18699-87-1, molecular formula is C6H6N2O2, 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.

Add to a 3 neck flask containing 500 mL of absolute ethanol under N2, 2.2 g (0.0956 g-atom) of sodium. After all the sodium reacts, add diethyl oxalate (98 mL) dropwise, and then add compound 2a-1 (one equivalent). The color turns from light yellow to brown upon addition. Allow the resulting solution to stand for two days at rt. Treat the orange mixture with SN HCl (pH=1), collect the precipitate by filtration and wash the filter cake with 100 mL EtOH and 200 mL di-isopropyl ether to afford 3a-1 as 2-hydroxy-3-(3-nitro-pyridin-2-yl)-acrylic acid ethyl ester (R4H, 20 g, 86%) or its tautomeric ketoester or as a mixture of keto-enol tautomers. 1H NMR (DMSO-d6) delta 8.83 (dd, 1H, J=1.1, 5.0 Hz), 8.65 (dd, 1H, J=1.5, 8.4 Hz), 7.56 (dd, 1H, J=5.0, 8.4 Hz), 7.11 (s, 1H), 3.47 (bs, 1H), 4.28 (q, 2H, J=7.1 Hz), 1.30 (t, 3H, J=7.0 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18699-87-1, its application will become more common.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/131012; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53174-98-4, 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 53174-98-4, name is Thieno[2,3-b]pyridine-2-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Example 161 N-(4-{trans-2-[(thieno[2,3-b]pyridin-2-ylmethyl)amino]cyclopropyl}phenyl)-3-(trifluoromethyl)benzamide hydrochloride By a method similar to Example 65, the title compound (10 mg) was obtained from N-[4-(trans-2-aminocyclopropyl)phenyl]-3-(trifluoromethyl)benzamide hydrochloride (75 mg) and thieno[2,3-b]pyridine-2-carbaldehyde (44.6 mg). MS (API+): [M+H]+ 468.0. 1H NMR (300 MHz, CD3OD) delta 1.36-1.57 (2H, m), 2.41 (1H, ddd, J = 10.2, 6.5, 3.7 Hz), 3.01 (1H, dt, J = 7.6, 4.0 Hz), 4.73 (2H, s), 7.07 (2H, d, J = 8.7 Hz), 7.44-7.54 (2H, m), 7.61 (2H, d, J = 8.7 Hz), 7.70-7.79 (1H, m), 7.90 (1H, d, J = 7.9 Hz), 8.15-8.30 (3H, m), 8.58 (1H, dd, J = 4.7, 1.5 Hz).

According to the analysis of related databases, 53174-98-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TOMITA, Naoki; KAJII, Shigeo; CARY, Douglas Robert; TOMITA, Daisuke; IMAMURA, Shinichi; TSUCHIDA, Ken; MATSUDA, Satoru; HARA, Ryujiro; EP2743256; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 171919-37-2 , The common heterocyclic compound, 171919-37-2, name is 1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, molecular formula is C9H8N2O2, 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 suspension of 1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (10.0 g, 56.8 mmol), prepared as described above in Alternative A or B, in anhydrous DCM (390 mL) cooled on ice, oxalyl chloride (14.4 mL, 170.4 mmol) was added dropwise over 15 mm and the mixture was stirred at room temperature for 2 h. The mixture was then concentrated in vacuo to give a yellow solid, which was treated with tert-butanol (300 mL, 3.14 mol), followed by an addition of potassium tert-butoxide (10.2 g, 91 mmol). The resulting mixture was stirred at room temperature for 16 h and then concentrated in vacuo. The crude was purified by flash column chromatography (Silica 120 g, 0-10% MeOH in DCM) to give the product (12.6 g, 86%) as a light brown solid. UPLC-MS (Acidic Method, 2 mm): rt 1.10 mm, m/z 233.1 [M+H]. ?HNIVIR (400 MHz, DMSO-d6) ppm 8.35 (dd, J= 4.6, 1.6 Hz, 1H), 8.27 (dd, J= 7.8, 1.6 Hz, 1H), 8.20 (s, 1H), 7.27 (dd, J= 7.9, 4.6 Hz, 1H), 3.86 (s, 3H), 1.56 (s, 9H).

The synthetic route of 171919-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; KINCAID, John; DUNCTON, Matthew; (142 pag.)WO2018/213810; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-01-8, 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. 17282-01-8, name is 3-Bromo-2-fluoro-5-picoline. A new synthetic method of this compound is introduced below.

To a solution of B9.1 (300 mg, 1.596 mmol) in THF(10 mL) at -78 oC was added LDA (2 M, 0.8 mL) and the mixture was stirred at -78 oC for 2 h. The mixture was quenched by10 mL H2O and extracted with EtOAc (10 mL x 3). The combined organic phase was concentrated to give the crude product, which was purified by flash chromatography (Normal phase, silica gel, PE_EtOAc=0-100%, UV254 & UV280) to give the title compound (130 mg , 43%) as a yellow oil. 1H-NMR (400 MHz, CDCl3) delta ppm 2.37 (s, 3H), 7.19 (d, 1H), 8.05 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-01-8, its application will become more common.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue; ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (193 pag.)WO2017/221092; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3678-62-4 ,Some common heterocyclic compound, 3678-62-4, molecular formula is C6H6ClN, 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.

1Og of 2-chloro-4-methylpyridine are dissolved in 50 ml of CH3CN and heated to- 85C. Then a mixture of 32g N-Chlorosuccinimid and l,6g AIBN is added over a period of 5 minutes. The. resulting, mixture is refluxed for two hours, then the solvent is removed in vacuo, the residue treated with 100ml of CH2Cl2 and washed with water 2 times. The organic phases are collected, dried over Na2S04 and the residue obtained after evaporation of the solvent is distilled (80C, 100 mTorr). Yield 79%

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. 3678-62-4, 2-Chloro-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; WO2006/10643; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.185017-72-5, name is 3-Bromo-2-chloro-6-picoline, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.name: 3-Bromo-2-chloro-6-picoline

In 21 mL of carbon tetrachloride, 3-bromo-2-chloro-6-methylpyridine (880 mg, 4.26 mmol) was dissolved, and N-bromosuccinimide (682 mg, 3.83 mmol) and AIBN (70 mg, 0.426 mmol) were added, followed by stirring at 90C for one hour. The resulting reaction solution was concentrated, and the residue thus obtained was purified by silica gel column chromatography (chloroform/methanol = 100/0 to 95/5), whereby 3-bromo-6-(bromomethyl)-2-chloropyridine was obtained as a crude purified product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,185017-72-5, 3-Bromo-2-chloro-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SUGIMOTO, Tetsuya; TAKAHASHI, Hidekazu; MITSUYA, Morihiro; MASUKO, Norio; SOOTOME, Hiroshi; EP2821406; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem