Tag: M.W:100-200

Application of 153813-70-8, Adding some certain compound to certain chemical reactions, such as: 153813-70-8, name is 3-Nitroisonicotinaldehyde,molecular formula is C6H4N2O3, 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 153813-70-8.

Method 30; zain _) acryl Methyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate (1.73g, 5.82 mmol) was dissolved in dry THF (20mL) and cooled to -78C under nitrogen. Tetramethylguanidine (638mg., 5.55 mmol) was added and the solution stirred at -78C for a further 10 mins. A solution of 3-nitroisonicotinaldehyde (Method 31, 804mg, 5.29mmol) in dry THF (5mL) was added dropwise. The resulting deep red solution was stirred for 2hrs. at – 78C, then poured into a mixture of ethyl acetate (100mL) and water (50mL). The organic layer was separated, washed with water (2 x 50mL) and brine (25mL), dried (MgSO4) and evaporated under reduced pressure to give a yellow oil, which was purified by column chromatography (EtOAc: isohexane 1:1) to give the title compound as a 10:1 mixture of Z/E isomers (1.57 g, 92%). 1H NMR 1.3 (s, 9H); 1.4 (s, 0.9H); 3.55 (s, 0.3H); 3.8 (s, 3H); 6.6 (s, 0.1H); 7.2 (s, 1H); 7.25(d, 0.1H); 7.5 (d, 1H); 8.75 (d, 0.1H); 8.8 (s, 1.1H); 8.85 (d, 1H); 9.2 (s, 0.1H); 9.25 (s, 1H); MS m/z 322.

According to the analysis of related databases, 153813-70-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2003/74532; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19235-89-3, 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 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To isopropanol (30.0 mL) was added sodium hydride (0.606 g of 60% dispersion, 15.2 mmol) in small portions over 5 minutes. The resulting gel-like suspension was stirred for an additional 5 minutes at room temperature. 2-Chloro-4-cyanopyridine (2.00 g, 14.4 mmol) was then added in one portion and the resulting solution was heated to reflux. After 1 hour, the reaction mixture was allowed to cool to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried (magnesium sulfate) and concentrated to provide a yellow oil. Flash chromatography over silica (hexanes/ethyl acetate) afforded 1.25 g (53%) of product as a colorless oil: 1H NMR (CDCl3) delta 8.27 (d, J=5.2 Hz, 1H), 7.01 (dd, J=5.2, 1.4 Hz, 1H), 6.91 (d, J=1.4 Hz, 1H), 5.31 (sept, J=6.2 Hz, 1H), 3.33 (d, J=6.2 Hz, 6H) ppm.

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 19235-89-3, 4-Chloropyridine-2-carbonitrile.

Reference:
Patent; Genzyme Corporation; US2005/176761; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 847729-27-5 ,Some common heterocyclic compound, 847729-27-5, molecular formula is C7H5ClFNO2, 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.

Description 90: methyl 5-fluoro-2-(3-((4-fluoro-2- methylphenyl)amino)azetidin-1-yl)nicotinate (D90)A mixture of methyl 2-chloro-5-fluoronicotinate (D69) (199.85 mg, 1 .054 mmol) and potassium carbonate (291 mg, 2.108 mmol) in tetrahydrofuran (2ml) was stirred under N2 nitrogen 15 min at room temperature. N-(4-fluoro-2- methylphenyl)azetidin-3-amine (D55) (190 mg, 1 .054 mmol) was added and the resulting mixture was stirred 1 day at room temperature. The residue obtained after solvent evaporation was purified by Biotage SNAP-Si column eluting with a mixture cyclohexane/ethyl acetate from 100/0 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D90)(155 mg)MS: (ES/+) m/z: 334.6 [MH+] C17H17F2N302 requires 333.331 H NMR (400MHz ,CHLOROFORM-d) delta = 8.24 (d, J = 2.9 Hz, 1 H), 7.80 (dd, J = 2.9, 8.3 Hz, 1 H), 6.91 – 6.75 (m, 2 H), 6.32 (dd, J = 4.9, 8.3 Hz, 1 H), 4.50 (dd, J = 7.3, 9.3 Hz, 2 H), 4.40 – 4.27 (m, 1 H), 3.97 – 3.81 (m, 5 H), 3.72 (d, J = 6.4 Hz, 1 H), 2.18 (s, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,847729-27-5, its application will become more common.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-79-4, 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. 128071-79-4, name is 4-Bromo-2-fluoro-3-methylpyridine. A new synthetic method of this compound is introduced below.

To a reaction flask containing a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (5.93 g, 20.17 mmol) in Dioxane (120 mL) were added 4-bromo-2-fluoro-3-methylpyridine (3.72 g, 19.58 mmol), Water (40.0 mL) and Na2C03 (8.30 g, 78 mmol). After the mixture was degassed with Ar for 10 min, Pd(Ph3P)4 (1.131 g, 0.979 mmol) was added. The flask was sealed and the mixture was heated to 100 C over night. The reaction mixture was cooled down and diluted with EtOAc and water, plus sonication to break up solids, then transferred to a separation funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2S04, filtered and concentrated in vacuo to afford a white precipitate in a pale gold residue. The extract was purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give (0534) Intermediate 27B (gold pale oil, 5.01 g, 17.72 mmol, 91% yield). LC-MS Anal. Calc’d for C16H20FNO2 277.15, found [M+H] 278.1. Tr = 1.02 min (Method A). NMR (400MHz, chloroform-d) delta 7.94 (d, J=5.0 Hz, 1H), 6.89 (dd, J=5.1, 0.9 Hz, 1H), 5.79 – 5.49 (m, 1H), 4.18 (q, J=7.1 Hz, 2H), 2.55 – 2.28 (m, 4H), 2.26 – 2.11 (m, 5H), 2.00 – 1.86 (m, 2H), 1.55 – 1.41 (m, 1H), 1.29 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-79-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65515-39-1, 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.65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, molecular weight is 162.19, as common compound, the synthetic route is as follows.

(a) 4-ethyl-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (3.5 g, 21.58 mmol) in THF (100 mL) was added LHMDS (1M in THF) (22.66 mL, 22.66 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction was stirred at this temperature for 1 h. lodomethane (2.418 mL, 22.66 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride (60 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2x). The combined organics were dried over Na2S04, filtered, concentrated, and purified by flash chromatography (0-5% EtOAc in hexanes, 80 g column; re-columned using 0-5% EtOAc in hexanes, 80 g column) to afford 4-ethyl-2-methoxy-6-methylnicotinonitrile (2.01 g, 90% purity) as a white crystalline solid. LC-MS(ES) m/z = 176.9 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 65515-39-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 910656-00-7, 4-Amino-N-methylnicotinamide, 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, HPLC of Formula: C7H9N3O, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9N3O

4-Amino-Lambda/-methyl-3-pyridinecarboxamide (200 mg; may be prepared as described in intermediate 121 ) was dissolved in DMF (20.00 ml_). DMAP (8.08 mg), N,N- diisopropylethylamine (0.462 ml.) and chloroacetyl chloride (0.212 ml.) were added at room temperature under stirring. The mixture was heated in the microwave for 10 min at100 0C. The mixture was diluted with EtOAc (10 ml) and washed with water and brine ( x3). Organics were dried over sodium sulphate, filtered and the solvent was evaporated to afford the crude product that was purified by silica chromatography to afford the title compound (100 mg, 0.395 mmol). m/z [M+H]+: 228.1 / 230.1. Retention time 0.44 min (LC/MS method 3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,910656-00-7, 4-Amino-N-methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23628-31-1, 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. 23628-31-1, name is 6-Aminopicolinic acid, molecular formula is C6H6N2O2, 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.

Example 6. Synthesis of N-(6-(morpholinomethyl)pyridin-2-yl)-2-(2- (trifluoromethyl)phenyl)benzo[d]oxazole-7-carboxamide (Compound 125) : Step 1) Preparation of ethyl 6-aminopicolinate (20): 19 20To a solution of 2-amino-6-pyridinecarboxyric acid (19; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 20 (5.5 g, 76%).

According to the analysis of related databases, 23628-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; VU, Chi, B.; WO2010/19606; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 853909-08-7, 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. 853909-08-7, name is 5-Ethynyl-2-fluoropyridine, molecular formula is C7H4FN, 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.

Under an argon atmosphere, Au(PPh3)Cl (488 mg, 0.99 mmol), 6-fluoro-3-pyridylethyne (179 mg, 1.48 mmol) and ethanol (20 ml) were added to a 20 ml Schlenk tube, and then sodium ethoxide (408 mul, 1.04 mmol: 2.55 mol/L (liter) in ethanol solution) was added dropwise thereto and the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the resulting white precipitate was filtered and successively washed with ethanol (12 ml .x. three times), water (12 ml .x. three times) and ethanol (6 ml .x. three times), followed by drying under vacuum to give 0.42 g of the desired compound as a yellow powder (yield: 73percent). 1H-NMR (400 MHz, CDCl3) delta: 8.35 (s, 1H), 7.81-7.87 (m, 1H), 6.80-6.84 (m, 1H) (FAB-MS) (M/Z): 580 (M+H)+ Luminescence analysis: (CHCl3, 77K, Ex250nm) lambda (nm): 413, 433, 442, 452 Elemental analysis: Found C: 51.76, H: 3.05, N: 2.51 Theoretical C: 51.83, H: 3.13, N: 2.42

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 853909-08-7, 5-Ethynyl-2-fluoropyridine.

Reference:
Patent; Ube Industries, Ltd.; EP1847545; (2007); 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, the common compound, a new synthetic route is introduced below. name: Pyrazolo[1,5-a]pyridine-2-carboxylic acid

Reference Example 43-1 (R)-2-methyl-N-((R)-1-(pyrazolo[1,5-a]pyridin-2-yl)ethyl)propane-2-sulfinamide Pyrazolo[1,5-a]pyridine-2,3-dicarboxylic acid dimethyl ester (3.35 g, 14 mmol) was dissolved in 50% sulfuric acid (110 mL), and the solution was stirred for 2.5 hours at 80C. The reaction liquid was cooled to 0C, and a 8 M aqueous solution of sodium hydroxide was added thereto to adjust the pH to 9. Subsequently, the pH was adjusted to 3 with 6 M hydrochloric acid. A suspension liquid thus produced was separated by filtration, and crystals were washed with water and then dried under reduced pressure. Thus, pyrazolo[1,5-a]pyridine-2-carboxylic acid (pale brown crystals, 1.88 g, 81%) was obtained. In a nitrogen atmosphere, pyrazolo[1,5-a]pyridine-2-carboxylic acid (941 mg, 5.8 mmol) thus obtained was dissolved in THF (30 mL), and the solution was stirred for a while at room temperature. Subsequently, a THF solution of a borane-THF complex (20 mL, 18 mmol, 0.9 M) was added to the solution, and the mixture was stirred for 3.5 hours at 70C. The reaction liquid was cooled to 0C, water was added thereto, and the mixture was stirred for a while. Subsequently, 6 N hydrochloric acid was added thereto, and the mixture was heated to reflux for one hour. The solvent was distilled off under reduced pressure, subsequently methanol was added thereto, and the solvent was distilled off again. A residue thus obtained was diluted with ethyl acetate, and the organic layer was washed with a 1 N aqueous solution of sodium hydroxide, water, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, insoluble matters were filtered, and then the solvent was distilled off under reduced pressure. Thus, pyrazolo[1,5-a]pyridin-2-ylmethanol was obtained. According to a technique similar to that of Reference Example 13-3, pyrazolo[1,5-a]pyridine-2-carboaldehyde was obtained using pyrazolo[1,5-a]pyridin-2-ylmethanol thus obtained. According to a technique similar to that of Reference Example 1-2, (R)-2-methyl-N-(pyrazolo[1,5-a]pyridin-2-ylmethylene)propane-2-sulfinamide was obtained using pyrazolo[1,5-a]pyridine-2-carboaldehyde thus obtained and (R)-2-methylpropane-2-sulfinamide. According to a technique similar to that of Reference Example 1-3, the title compound (pale yellow oily material, 498 mg, 65%) was obtained using (R)-2-methyl-N-(pyrazolo[1,5-a]pyridin-2-ylmethylene)propane-2-sulfinamide thus obtained.

The synthetic route of 63237-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; Kinki University; TANAKA Hiroto; OOI Isao; MOGI Yuzo; HIROSE Masaaki; ENDO Tsuyoshi; OGAWA Toru; KAWABATA Atsufumi; (171 pag.)EP3404021; (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. 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, molecular formula is C6H3F4NO, 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. Application In Synthesis of 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one

A mixture of 2 (100 mg, 93.1% purity, 0.49 mmol), pyridone (1 17 mg, 97.6% purity, 0.49 mmol) and K2CO3 (82 mg, 0.59 mmol) in DMF (0.5 ml) was aged with stirring at ambient temperature for 3h. After the reaction was completed, the batch was taken on to the next step without further work up or isolation.

With the rapid development of chemical substances, we look forward to future research findings about 1227594-89-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ITOH, Tetsuji; JEON, Ingyu; MANGION, Ian; QIAN, Gang; SHERRY, Benjamin, D.; GAUTHIER, Donald, R.; CAO, Yang; WO2014/89140; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem