Category: pyridine-derivatives

Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. 31181-90-5, formula is C6H4BrNO, Name is 5-Bromopicolinaldehyde. TThe standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Reference of 31181-90-5.

Ahemed, Jakeer;Pasha, Jakeer;Rao D, Venkateshwar;Kore, Ranjith;Gade, Ramesh;Bhongiri, Yadagiri;Chetti, Prabhakar;Pola, Someshwar research published 《 Synthesis of new Zn (II) complexes for photo decomposition of organic dye pollutants, industrial wastewater and photo-oxidation of methyl arenes under visible-light》, the research content is summarized as follows. Synthesis of new Schiff′s base Zn-complexes for photo-oxidation of Me arenes and xylenes are reported under visible light irradiation conditions. All the synthesized new ligands and Zn-complexes are thoroughly characterized with various spectral analyses and confirmed as 1:1 ratio of Zn and ligand with distorted octahedral structure. The bandgap energies of the ligands are higher than its Zn-complexes. These synthesized new Zn(II) complexes are used for the photo-fragmentation of organic dye pollutants, photodegradation of food industrial wastewater and oxidation of Me arenes which are converted into its resp. aldehydes with moderate yields under visible light irradiation The photooxidation reaction dependency on the intensity of the visible light was also studied. With the increase in the dosage of photocatalyst, the Me groups are oxidized to get aldehydes and mono acid products, which are also identified from LC-MS data. Finally, [Zn(PPMHT)Cl] is with better efficiency than [Zn(PTHMT)Cl] and [Zn(MIMHPT)Cl] for oxidation of Me arenes is reported under visible-light-driven conditions.

31181-90-5, 5-Bromopyridine-2-carbaldehyde is a useful research compound. Its molecular formula is C6H4BrNO and its molecular weight is 186.01 g/mol. The purity is usually 95%.

5-Bromopyridine-2-carbaldehyde is a water soluble organic molecule that has been shown to inhibit the mitochondrial respiratory chain. It is a structural analog of the natural substrate for mitochondrial cytochrome c oxidase, 5-aminolevulinic acid. This compound has been shown to be selective against cancer cells and has anti-viral properties. The photophysical properties of 5-bromopyridine-2-carbaldehyde have been studied extensively. The fluorescence quantum yield of this molecule in aqueous solution is 0.06%., Reference of 31181-90-5

Referemce:
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

Reference of 107867-51-6 ,Some common heterocyclic compound, 107867-51-6, molecular formula is C6H6F3N3, 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 solution of Intermediate 18 (150 mg, 0.436 mmol) in DMSO (8.0 ml) was treated with 5-(trifluoromethyI)pyridine-2,3-diamine (85 mg, 0.479 mmol) and the mixture stirred at 70C for 2 h. After cooling to room temperature the reaction was quenched with water to afford a precepitate. The precepitate was filtered off and washed with water. The filtered solid was dissolved in EtOAc and washed with NaHC03, brine, and dried (MgS04) and concentrated. Trituration of the solid from ether / hexane followed by filtration afforded 143 mg of Methyl 2-(Cis-3-(5-(3-fluoro-4-(6-(trifluoromethyl)-3H-imidazo[4,5-)]pyridin-2-yl)phenyl)pyrimidin-2-yloxy)cyclobutyl)acetate as a tan solid. LC-MS (M+l)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,107867-51-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; BALKOVEC, James, M.; KRIKORIAN, Arto, D.; MILLER, Daniel, J.; GUIADEEN, Deodial; YANG, Ginger Xu-Qiang; JIAN, Tianying; WU, Zhicai; YU, Yang; NARGUND, Ravi, P.; VACHAL, Petr; HE, Shuwen; LAI, Zhong; HONG, Qingmei; DEVITA, Robert, J.; KIM, David; TING, Pauline, C.; WO2013/74387; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 898746-42-4 , The common heterocyclic compound, 898746-42-4, name is 6-Fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5FN2, 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.

6-Fluoro-1H-pyrrolo[2,3-b]pyridine (2.50 g, 18.36 mmol)Soluble in DMF (50mL),Cool to 0 C,Then add bromine to it(3.20g, 20.00mmol)DMF (20 mL) solution,After the dropwise addition was completed, the resulting reaction solution was stirred at room temperature for 2 hours.Then water (100 mL) was added and a large amount of solid precipitated.Filter under reduced pressure, and the filter cake was washed with water (30 mL×2).Then dried under vacuum at 60 C for 24 hours.The title compound was obtained as a white solid (3.44 g, 87%).

The synthetic route of 898746-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; Nie Biao; Xu Juan; Yan Huan; Chen Jianping; (90 pag.)CN108727369; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem