Tag: M.W:100-200

Reference of 22620-34-4, 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 22620-34-4, name is (5-Chloro-3-pyridinyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (5-chloropyridin-3-yl)methanol (292 mg, 2.03 mmol) in dry DCM (10 ml) Mn02 (3.54 g, 40.6 mmol) was added. The mixture was stirred at rt o.n. The solid was filtered (washing with DCM) and the solution was evaporated to dryness to give the title compound (128 mg, 0.9 mmol, purity: 85 % by NIVIR, recovery: 44 %). MS (m/z) 142, 144(M+H).

According to the analysis of related databases, 22620-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BANDYOPADHYAY, Deepak; DAUGAN, Alain Claude-Marie; DONCHE, Frederic G.; EIDAM, Patrick M.; FAUCHER, Nicolas Eric; GEORGE, Nicolas S.; HARRIS, Philip Anthony; JEONG, Jae U.; KING, Bryan W.; SEHON, Clark A.; WHITE, Gemma Victoria; WISNOSKI, David Duff; (177 pag.)WO2016/185423; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 403-45-2, 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 403-45-2 as follows.

To a stirred and refluxed solution of 6-fluoro-nicotinic acid (0.092 g, 6.52 mmol) in benzene and 2-methyl-propan-2-ol (2: 1,15 : 7 mL) was added dropwise N, N- [DIMETHYLFORMAMIDE] di-tert-butyl acetal (8.2 mL, 29.6 mmol). The reaction mixture was refluxed for 3 hours, cooled to room temperature and partitioned between aqueous [NAHC03] and dichloromethane. The organic layer was washed with water and brine, dried [(MGS04),] filtered, concentrated under reduced pressure and purified by flash chromatography with 15% to 30% ethyl acetate in hexane to provide the titled compound. MS (CI) m/z 197 (M+1) [+] [; IH] NMR (300 MHz, CDC13) [5] ppm 8.82 (d, 1H), 8.38 (m, 1H), 6.98 (d, [1H),] 1.64 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,403-45-2, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89488-30-2 ,Some common heterocyclic compound, 89488-30-2, molecular formula is C6H6BrNO, 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.

5-Bromo-1,3-dimethyl-1H-pyridin-2-one B-1 To a suspension of 5-bromo-2-hydroxy-3-methyl pyridine A1 (1.000 g; 5.053 mmol) and potassium carbonate (1.397 g; 10.105 mmol) in DMF (5.000 ml) is carefully added iodomethane (0.346 ml; 5.558 mmol). The reaction mixture is stirred overnight (16 h) at room temperature. The reaction mixture is then quenched with 10% ammonia solution (10 ml) and 30 ml water is added. It is extracted with 3*50 ml EtOAc. The combined organic layer is dried with Na2SO4, filtered and concentrated under reduced pressure to afford the product. Yield: 98% (1.0 g; 4.95 mmol) HPLC-MS: (M+H)+=202/204; tRet=0.65 min; method LCMS BAS1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89488-30-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; MARTIN, Laetitia; SMETHURST, Christian; US2015/51208; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3678-62-4, 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.3678-62-4, name is 2-Chloro-4-methylpyridine, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.

lOg of 1.-.2-Ghlar6-4-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 CH2C12 ?? 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%

The chemical industry reduces the impact on the environment during synthesis 3678-62-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AVENTIS PHARMA S.A.; WO2006/10642; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 92138-35-7, name is 6-Chloro-3-nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Recommanded Product: 6-Chloro-3-nitropyridin-2(1H)-one

Intermediate 63-Aminopyridin-2(l//)-one hydrochlorideTo a stirred solution of 6-chloro-3-nitropyridin-2(lH)-one (Intermediate 5, 3.5 g, 20 mmol) in ethyl acetate (50 mL) was added SnCl2.H2O(32 g, 142 mmol) in portions over a period of 15 min at room temperature, then the mixture was re fluxed at 80 0C for 3 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and neutralized with solid NaHCO3 (50 g). The mixture was filtered and the solids were washed with ethyl acetate (2 x 50 mL). The filtrate was concentrated to remove ethyl acetate under vacuum and the residue was taken in ice cold dioxane (20 mL). 4N HCl in dioxane (10 mL) was added and the mixture was concentrated to give desired product in 95%yield (3.5 g, 19 mmol).MS (ES): 143.2 (M-I) for C5H5ClN2O1H-NMR (CDCl3, 300 MHz): delta 4.20 (br s, 2H), 6.20 (d, J= 7.6 Hz, IH), 6.59 (d, J= 7.6 Hz,IH).

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, 92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27732; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 182181-42-6, 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.182181-42-6, name is 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine, molecular formula is C9H9ClN2, molecular weight is 180.63, as common compound, the synthetic route is as follows.

EXAMPLE 55 2-[[4-(2,4-Dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine monomaleic acid salt. Refer to Chart E A mixture of 2-(chloromethyl)-8-methylimidazo[1,2-a]pyridine (Example 54, Step 1; 0.294 g), 1-(2,4-dichlorophenyl)piperazine (Example 31, Step 1; 0.396 g) diisopropylethylamine (0.35 mL), and THF (2 mL) is heated at 75 C. for 5 hours. The mixture is then concentrated under reduced pressure, partitioned between saturated aq. sodium bicarbonate and dichloromethane, and the combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) and the appropriate fractions are combined and concentrated to give 2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine.

Statistics shows that 182181-42-6 is playing an increasingly important role. we look forward to future research findings about 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine.

Reference:
Patent; Pharmacia & Upjohn Company; US5912246; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13269-19-7, 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. 13269-19-7, name is 2-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

General procedure: choloro acetylcholoride (24mmol) and Et3N (24mmol) was added to a solution of 2-chloro-3-aminopyridine 7e (20mmol) in CH2Cl2 (20mL) at room temperature. The mixture was stirred for 5 hrs, and the solvent was evaporated under vacuum. The residue was purified by column chromatography (CH2Cl2:CH3OH: 30:1) on silica gel to obtain pure compound 8e as a white powder in 72% yield. To a solution of amide derivative 8e (5mmol) and potassium carbonate (7.5mmol) in acetonitrile (20ml) was added isothiocyanate (6mmol) during about 5min. The reaction mixture was stirred at room temperature overnight, and the solvent was evaporated under vacuum. The residue was extracted with ethyl acetate (20mL×3). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The obtained residue was purified by silica gel flash chromatography column (CH2Cl2:CH3OH: 30:1) to afford 5l as a white solid in 82% yield. To a solution of 5l (1mmol) in glacial acetic acid (5mL) were added aldehyde 6b (1mmol) and beta-alanine (1mmol). The resulting mixture was stirred under reflux for 2h. Upon completion of the reaction, the mixture was cooled, the reaction was quenched with water, and the precipitate was filtered off, then the residue was purified by column chromatography (CH2Cl2:CH3OH: 15:1) on silica gel to obtain pure compound 2r as a faint yellow powder in 80% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13269-19-7, its application will become more common.

Reference:
Article; Cai, Ming-Guang; Wu, Yang; Chang, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2517 – 2520;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22280-60-0, 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. 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

Step 1: 6-Chloro-2-methylpyridin-3-amine (44). To a stirred solution of 43 (5 g, 29 mmol) in EtOH (20 mL) and cone. HCI (20 mL) was added Fe powder (16.2 g, 289 mmole) in small portions at RT over 30 min. Stirring was continued at RT for another 30 min. The solvent was distilled off under reduced pressure. Water was added and the resulting mixture was neutralized with NaHC03. EtOAc was added and the biphasic mixture was filtered through Celite and washed with EtOAc. The phases of the filtrate were separated and the organic layer was washed with water, brine, dried over Na2S04, and concentrated to afford 44 (4.1 g, 99 %) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; XU, Wei; (106 pag.)WO2017/4608; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56673-34-8, 3-Bromo-6-mercaptopyridine, 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, name: 3-Bromo-6-mercaptopyridine, blongs to pyridine-derivatives compound. name: 3-Bromo-6-mercaptopyridine

Powdered sodium methoxide (1.08 g, 19.95 mmol) and 1-bromo-3-chloropropane (2.87 mL, 28.7 mmol) were added to a stirred suspension of 5-bromopyridine-2-thiol (3.16 g, 16.63 mmol) in anhydrous methanol (80 mL). The mixture was heated at 60C and stirred under N2 for 1.5 h. After cooling to room temperature, the mixture wasquenched with water-brine (1:1, 100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic fraction was washed with brine (50 mL), then dried (MgSO4) and reduced in vacuo, to give the title compound (3.92 g, 88%) as a yellow solid. H (500 MHz, CDC13) 8.50-8.44 (m, 1H), 7.58 (dd,J8.5, 2.4 Hz, 1H), 7.07 (dd,J8.5, 0.6 Hz, 1H), 3.67 (t,J6.4 Hz, 2H), 3.29 (t,J6.9 Hz, 2H), 2.17 (p,J6.6 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56673-34-8, 3-Bromo-6-mercaptopyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki Peter; BENTLEY, Jonathan Mark; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; CHOVATIA, Praful Tulshi; DEBOVES, Herve Jean Claude; JOHNSTONE, Craig; JONES, Elizabeth Pearl; KROEPLIEN, Boris; LECOMTE, Fabien Claude; MADDEN, James; MILLER, Craig Adrian; PORTER, John Robert; SELBY, Matthew Duncan; SHAW, Michael Alan; VAIDYA, Darshan Gunvant; YULE, Ian Andrew; WO2015/86506; (2015); 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. 100202-78-6, name is 2-(Bromomethyl)-6-fluoropyridine, molecular formula is C6H5BrFN, 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. Quality Control of 2-(Bromomethyl)-6-fluoropyridine

General procedure: Hexamethylenetetramine (159 mg, 1.13 mmol, 1.0 eq.) was added under stirring to a solution of 10-6a or 10-6b (1.0 eq.) in chloroform (15 mL). The resulting mixture was stirred at 50C for 1 hour. After cooling to rt, the solvent was removed under reduced pressure. The residue was dissolved with ethanol (10 mL) and concentrated hydrochloric acid (0.5 mL) was added. This mixture was stirred at 50C for 2 hours and at room temperature overnight. The solvent was then evaporated under reduced pressure to give the desired crude products 10a (white solid) or 10b (yellow solid) which were used in the next step without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 100202-78-6.

Reference:
Article; Wenzel, Barbara; Liu, Jianrong; Dukic-Stefanovic, Sladjana; Deuther-Conrad, Winnie; Teodoro, Rodrigo; Ludwig, Friedrich-Alexander; Chezal, Jean-Michel; Moreau, Emmanuel; Brust, Peter; Maisonial-Besset, Aurelie; Bioorganic Chemistry; vol. 86; (2019); p. 346 – 362;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem