Day: April 12, 2022

Electric Literature of 18368-73-5 ,Some common heterocyclic compound, 18368-73-5, 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.

To a solution of 250 mg (1.86 mmol) of terephthalaldehyde 70, 618 mg (4.47 mmol) of nitropicoline 63 in 8 mL of THF was added 4.47 mL (4.47 mmol) of a 1 M solution of TBAF and 732 mg (5.59 mmol) of Huenig’s base. The mixture was stirred at 60 C for 3 days. The crude reaction mixture was concentrated under reduced pressure onto 1 g of silica gel and purified by silica gel chromatography with a gradient of 0e55% EtOH/EtOAc:hexane to afford 400 mg (68%) of dimeric furopyridine 73 as a colorless solid: mp 157e158 C; 1 H NMR (500 MHz, CDCl3) d 3.23 (dd, 2H, J 16.1 and 7.6 Hz), 3.71 (dd, 2H, J 16.1 and 9.4 Hz), 5.86 (dt, 2H, J 9.4 and 7.6 Hz), 6.85 (m, 2H), 7.45 (s, 4H), 7.50 (m, 2H), 8.01 (d, 2H, J 5.0 Hz); 13C NMR (125 MHz, CDCl3) d 36.4, 36.5, 8.10, 116.7, 119.0, 125.6, 133.4, 141.0, 146.6, 167.7. Anal. Calcd. For C20H16N2O2: C, 75.93; H, 5.10; N, 8.86. Found: C, 75.76; H, 4.98; H, 8.79.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18368-73-5, its application will become more common.

Reference:
Article; Kuethe, Jeffrey T.; Tetrahedron; vol. 75; 34; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 182181-42-6, 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 182181-42-6, name is 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Production Example 28; 1.52 g of 2- (chloromethyl)-8-methylimidazo [1, 2- pyridine and 1.36 g of (3,3, 3- trifluoropropyl) malononitrile were dissolved in 20 ml of N, N-dimethylformamide, and 1.16 g of potassium carbonate was then added under ice-cooling. The mixture was stirred at room temperature for 7 hours. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized form hexane-ethyl acetate to obtain 1.50 g of a compound represented by the following formula: (hereinafter, referred to as the present compound (28)). 1H-NMR (CDCl3, TMS, 8 (ppm) ): 2. 38-2. 42 (2H, m), 2.54-2. 66 (2H, m), 2.57 (3H, s), 3.53 (2H, s), 6.73 (1H, t), 7.00 (1H, dd), 7.66 (1H, s), 7.97 (1H, d)

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 182181-42-6, 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2005/68432; (2005); 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. 896139-85-8, name is Imidazo[1,2-a]pyridin-7-ol, the common compound, a new synthetic route is introduced below. Product Details of 896139-85-8

Imidazo[1,2-a]pyridin-7-ol (3 g, 0.023 mol), 2-(2-bromo-ethoxy)tetrahydro-2H-Pyran (3.6 mL, 0.023 mol) and K2CO3 (6.32 g, 0.05 mol) were heated in DMF (100 ml) for 3 hours. The solution was cooled and evaporated to dryness. The residue was taken up with DCM+MeOH, the solution was filtered through a celite layer and the filtrate was evaporated to dryness. The residue was purified by Normal phase on E 5424(Irregular SiOH 15-40 mum 300 g MERCK). Mobile phase (0.3% NH4OH, 97% DCM, 3% MeOH), yielding 1.49 g (24.8%) of intermediate shown.

The synthetic route of 896139-85-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2012/41000; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 30766-03-1, 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 30766-03-1 as follows.

A mixture of 4-bromopicolinic acid ( 15 g, 75 mmol), methanamine hydrochloride (1 5 g, 75 mmol), HOBt (10 g, 75 mmol), EDCI (21 g, 75 mmol) and Et3N (41.5 mL, 300 mmol) in DMF(200 mL) was stirred at r.t. for 18 h. Water was added to the reaction mixture and the resulting mixture was filtered to afford 16 g of 78 as solid which was used directly in the next step. LCMS: m/z 215 (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,30766-03-1, its application will become more common.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; WO2013/43232; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 697739-13-2, Imidazo[1,5-a]pyridine-8-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, Recommanded Product: Imidazo[1,5-a]pyridine-8-carboxylic acid, blongs to pyridine-derivatives compound. Recommanded Product: Imidazo[1,5-a]pyridine-8-carboxylic acid

To a suspension of Description 37 (2.0 g, 12.31 mmol) and triethylamine (1.89 ml, 13.54 mmol) in anhydrous toluene (75 ml) was added diphenylphosphoryl azide (2.92 ml, 13.54 mmol), and the resulting mixture heated at reflux for 1 hour. To this mixture was added 2-methyl-2-propanol (1.74 ML, 18.47 mmol) and heating continued overnight. The mixture was cooled and evaporated, and the residue purified by column chromatography on silica elution with 4% MEOH in DCM + 0.5% NH40H to give the title compound (1.85 g, 64%) as a white solid.

The synthetic route of 697739-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; WO2004/46133; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22280-60-0, Adding some certain compound to certain chemical reactions, such as: 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine,molecular formula is C6H5ClN2O2, 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 22280-60-0.

Step 3 6-Methoxy-2-memyl~3-mtropyridineA roundbottom flask was charged with a solution of 6-chloro-2-methyl-3- nitropyridine (12.0 g, 69.36 mmol) in methanol (100 ml). Sodium methanolate (5.6 g, 103.70 mmol) was added and the resulting solution was stirred at room temperature for 24 hours. The mixture was poured into 100 ml of water and the solids that formed were collected by filtration to afford the title compound.

According to the analysis of related databases, 22280-60-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/155156; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 20970-75-6, 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 20970-75-6, name is 2-Cyano-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a 500 mL single-neck round bottom flash fitted with a reflux condenser and a nitrogen outlet was added 10.1 g (86 mmol) 3-methylpicolinonitrile, 200 mL dimethyl carbonate, 18.2 g (103 mmol) N-bromosuccinimide and 2.1 g (8.5 mmol) benzoyl peroxide. The resulting reaction mixture was heated to 87 C and stirred for 5 h. Following this duration, the reaction mixture was cooled to ambient temperature and filtered, and the solid was rinsed with Et20. DCM was subsequently added to the filtrate and the resulting mixture was filtered. The combined organics were concentrated and the resulting semi-solid was purified by silica gel chromatography (2 x 330 g column, 5-35% EtOAc/Hexane) followed by reverse-phase HPLC (Waters Xbridge Prep C18 10 muetatauiota OBD, 50 x 250 mm column) to afford the title compound as a yellow solid (6.3 g, 32.0 mmol, 37% yield). LC-MS m/z 196.8 (M+H)+, 0.60 min (ret. time).

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 20970-75-6, 2-Cyano-3-methylpyridine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; COOPER, Anthony William James; GOODWIN, Nicole Cathleen; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; KERNS, Jeffrey K.; WILLEMS, Hendrika Maria Gerarda; YAN, Hongxing; (215 pag.)WO2018/109649; (2018); 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.903129-78-2, name is 6-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid, molecular formula is C8H5BrN2O2, molecular weight is 241.04, as common compound, the synthetic route is as follows.HPLC of Formula: C8H5BrN2O2

The compound of example 23 (1 .0 g, 4.15 mmol) was treated with pyridin-3-ylboronic acid (0.510 g, 4.15 mmol) in the presence of [1 ,1 ‘-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.102 g, 0.124 mmol) and sodium carbonate(0.829 g, 8.30 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.4 g (40.3 %); 1H NMR (DMSO-d6, 300 MHz): delta 7.54 (q, 1 H, J=4.8 Hz, Ar), 7.68-7.72 (m, 2H, Ar), 8.04 (s, 1H, Ar), 8.53-8.65 (m, 2H, Ar), 8.99 (d, 1H, J=1.8 Hz, Ar); 9.29 (d, 1H, J=1.8 Hz, Ar); MS (ES+): m/e 240 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,903129-78-2, 6-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate, molecular formula is C9H10ClNO2, 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.

Step 3. Synthesis of (beta-tert-butoxycarbonylamino-pyrjdin-S-yO-acetic acid ethyl ester. A 500 ml round-bottom-flask was charged with 2-chloropyndiotan- 3-yl) acetic acid ethyl ester (6 8 g, 34 0 mmol), tert-butyl carbamate (12 4 g, 105 mmol), 9,9-diotamethyl-4,5-biotas(diotaphenylphosphiotano)xanthene (4 2 g, 7 25 mmol), triotas(diotabenzyliotadeneacetone)diotapal.adiotaum (3 29 g, 3 59 mmol) cesium carbonate (16 9 g 51 87 mmol) and THF (165 mL) The mixture was heated and refluxed under argon for 20 hours Upon cooling, the reaction was quenched with 10% ammonium acetate solution and extracted with ethyl acetate The combined organic extracts were washed with water, brine dried and concentrated The residue was purified by silica gel chromatography eluted using a gradient of 2/98(v/v) EtOAc/hexanes to 10/90 (v/v) EtOAc/hexanes to afford 14 g of crude product ESI-MS m/z 225 (MH-C4He)+

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 197376-47-9, Ethyl 6-Chloropyridine-3-acetate.

Reference:
Patent; NOVARTIS INTERNATIONAL PHARMACEUTICAL LTD.; BURNS, Christopher, J.; GOSWAMI, Rajesh; JACKSON, Randy, W.; LESSEN, Thomas; LI, Weiping; PEVEAR, Daniel; TIRUNAHARI, Pavan, Kumar; XU, Hongyu; WO2010/130708; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 824-51-1, 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.824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H8N2, molecular weight is 132.16, as common compound, the synthetic route is as follows.

PREPARATION 135 3-Bromo-6-methyl-1 H-pyrrolo[2,3-b]pyridine The title compound of Preparation 58 (6.0 g, 45.4 mmol) was dissolved in 400 ml tetrahydrofuran. /V-Bromosuccinimide (8.1 g, 45.5 mmol) was added portion-wise, followed by the addition of concentrated sulfuric acid until the solution became turbid. The mixture was stirred at room temperature for 2 d. The solvent was evaporated under reduced pressure and the residue was resuspended in 2 N hydrochloric acid. The aqueous was washed twice with ether and was then carefully neutralised to pH 7- 8 with 32% sodium hydroxide solution, forming a precipitate. The solid was collected by filtration and was dried in a vacuum oven at 45 C overnight to give 8.21 g (38.9 mmol, 86%) of the title compound. Purity 100%. 1 H N MR (400 MHz, CH LOROFORM-d) delta ppm 2.66 (s, 3 H), 7.05 (d, J=8.21 Hz, 1 H), 7.27 (s, 1 H), 7.80 (d, J=8.21 Hz, 1 H), 9.58 – 9.62 (m, 1 H). UPLC/MS (3 min) retention time 1 .53 min. LRMS: m/z 21 1 , 213 (M+1 ).

The chemical industry reduces the impact on the environment during synthesis 824-51-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ALMIRALL, S.A.; VIDAL JUAN, Bernat; ALONSO DIEZ, Juan Antonio; BUIL ALBERO, Maria Antonia; EASTWOOD, Paul Robert; ESTEVE TRIAS, Cristina; LOZOYA TORIBIO, Maria Estrella; ROBERTS, Richard Spurring; VIDAL GISPERT, Laura; GONZALEZ RODRIGUEZ, Jacob; MIR CEPEDA, Marta; WO2013/10880; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem