Day: February 9, 2021

Electric Literature of 118650-08-1, Adding some certain compound to certain chemical reactions, such as: 118650-08-1, name is Methyl 2-(5-bromopyridin-3-yl)acetate,molecular formula is C8H8BrNO2, 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 118650-08-1.

Step 3: To a round-bottom flask containing (5-bromo-pyridin-3-yl)-acetic acid methyl ester (40 mg, 0.17 mmol), 2-[4-(2′-fluoro-2-trifluoromethyl-biphenyl-4- yloxymethyl)-phenyl]-4,4,5,5-tetramethyl-[l,3,2]dioxaborolane 13 (80 mg, 0.17 mmol), palladium acetate (6 mg, 0.026 mmol), 2-(dicyclohexylphosphino)biphenyl (18 mg, 0.051 mmol) and potassium fluoride (30 mg, 0.051 mmol) is added anhydrous 1,4-dioxane (2 ml). The flask is purged with argon and sealed. The mixture is stirred at 13O0C for 12 hours and then cooled to ambient temperature before water (5 ml) is added. The mixture is extracted with EtOAc (10 ml x 2), dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography (EtOAc/Hexane, gradient) to give {5-[4-(2′-fluoro-2- trifluoromethyl-biphenyl-4-yloxymethyl)-phenyl]-pyridin-3-yl} -acetic acid methyl ester 14: LC-MS m/z: 496.0 (M+l).

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. 118650-08-1, Methyl 2-(5-bromopyridin-3-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; WO2007/24922; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 32710-65-9 ,Some common heterocyclic compound, 32710-65-9, molecular formula is C6H2Cl2N2, 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.

Example 61Mol Weight: 218.70[00616] Synthesis of Intermediate (1)Molecular Weig ht: 173.00 Molecular Weight: 168.58[00617] In a 25-mL,3Nround-bottomed flask equipped with thermometer pocket fitted with a nitrogen inlet and a rubber septum, NaH (0.1 12 g, 1.0 eq.), methanol (0.1 1 mL, 1.0 eq.), suspended in N-Methyl pyrolidine (5 niL). The reaction mixture was stirred at 25-30C for 30 min. To this reaction mixture 2, 6-Dichloro,4-cyano-pyridine was added at 0-5 C. The progress of the reaction was followed by TLC analysis on silica gel with 10%EtOAc- hexane as mobile phase which shows completion after 2 h staring at 0-5 C. Reaction was quenched by water and precipitate was observed which was filtered and wash with hexane to give required compound (0.51 g, Crude). Reaction was stirred for 20 min with water and solid was separated and compound was collected by filtration and washed with hexane (30mL).Yield:0.51 g Crude.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,32710-65-9, its application will become more common.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SHECHTER, Sharon; KAUFFMAN, Michael; SANDANYAKA, Vincent, P.; SHACHAM, Sharon; WO2011/109799; (2011); 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. 95897-49-7, name is 7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine. A new synthetic method of this compound is introduced below., name: 7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine

Into a 100 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of n-BuLi in hexane (2.5 M, 2 mL, 5.0 mmol, 0.54 equiv) and a solution of n-Bu2Mg in heptanes (1.0 M, 4.8 mL, 4.8 mmol, 0.53 equiv). The resulting solution was stirred for 10 min at RT (20 C). This was followed by the dropwise addition of a solution of 7-bromo-2H,3H-[1,4]dioxino[2,3-b]pyridine (2 g, 9.26 mmol, 1.00 equiv) in tetrahydrofuran (16 mL) with stirring at -10 C in 10 min. The resulting mixture was stirred for 1 h at -10 C. The reaction mixture was slowly added to a solution of thionyl chloride (16 mL) at -10 C. The resulting mixture was stirred for 0.5 h at -10 C. The reaction was then quenched by the careful addition of 30 mL of saturated ammonium chloride solution at 0 C. The resulting mixture was extracted with 3×50 mL of dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluting with ethyl acetate/petroleum ether (1:3). This provided 1.3 g (60%) of 2H,3H-[1,4]dioxino[2,3-b]pyridine-7-sulfonyl chloride as a white solid. LCMS m/z: calculated for C7H6ClNO4S: 235.64; found: 236 [M+H]+.

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, 95897-49-7, 7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ERICSSON, Anna; GREEN, Neal; GUSTAFSON, Gary; HAN, Bingsong; LANCIA, JR., David R.; MITCHELL, Lorna; RICHARD, David; SHELEKHIN, Tatiana; SMITH, Chase C.; WANG, Zhongguo; ZHENG, Xiaozhang; (140 pag.)WO2018/175474; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 14482-51-0, 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. 14482-51-0, name is 2-Bromo-3,5-dichloropyridine. A new synthetic method of this compound is introduced below.

General procedure: 2,5-dibromopyridine (119 mg, 0.50 mmol), phenylacetylene (61 mg, 0.6 mmol), i-Pr2NH (101 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %), and CuI (9.5 mg, 5 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at reflux under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 200:1) to give the desired product 3i (117 mg, 91%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14482-51-0, 2-Bromo-3,5-dichloropyridine, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Bin; Chen, Rener; Jiang, Huajiang; Zhou, Qizhong; Qiu, Fangli; Han, Deman; Li, Rongrong; Tang, Wenyuan; Zhong, Aiguo; Zhang, Jie; Yu, Xiaochun; Tetrahedron; vol. 72; 22; (2016); p. 2813 – 2817;,
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. 10177-29-4, name is 4-Chloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

A 1.0 mol/L borane-tetrahydrofuran complex tetrahydrofuran solution (30 mL) was added to a solution of 4-chloronicotinic acid (1.58 g) in tetrahydrofuran (20 mL), followed by refluxing for 1.5 hours. 2.0 mol/L hydrochloric acid (10 mL) was added thereto, followed by refluxing for 1 hour. The reaction mixture was cooled to room temperature, and extracted with ethyl acetate. The organic layer was washed sequentially with a sodium carbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (ethyl acetate_methanol=1:0?9:1), whereby (4-chloro pyridin-3-yl)methanol (630 mg) was obtained as a white solid. (0954) MS(ESI m/z): 144 (M+H) (0955) RT(min): 0.77

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, 10177-29-4, 4-Chloronicotinic acid.

Reference:
Patent; FUJIFILM Corporation; KUBO, Yohei; ANDO, Makoto; TANAKA, Hidehiko; OSAKA, Shuhei; MATSUMOTO, Takuya; NAKATA, Hiyoku; TERADA, Daisuke; NITABARU, Tatsuya; (379 pag.)US2016/168139; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 70165-31-0, name is 6-Cyanonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 70165-31-0

EXAMPLE 1 5-Carboxy-2-(4,5-dihydro-2-thiazolyl)-pyridine Sodium (11 mmol) is added to a flask containing 75 ml of ethanol. As soon as the sodium has dissolved, 10 mmol of 5-carboxy-2-cyanopyridine and 11 mmol of 2-amino-ethanethiol are added and the solution is refluxed for 24 h. The solution is then diluted with 25 ml of water, made acidic (pH=5) with 2N HCl and evaporated. The residue is dissolved in 100 ml of hot chloroform, the salts are filtered off and the filtrate on cooling gives crystals of the title compound, m.p. 234-235 C. The starting material is prepared as follows:

With the rapid development of chemical substances, we look forward to future research findings about 70165-31-0.

Reference:
Patent; Zyma SA; US4904675; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 81719-53-1, Adding some certain compound to certain chemical reactions, such as: 81719-53-1, name is 3,5-Dichloropyridine-2-carboxylic Acid,molecular formula is C6H3Cl2NO2, 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 81719-53-1.

Example B9Preparation of compound 14: rac-3,5-dichloro-pyridine-2-carboxylic acid [3-(4-amino-6- methyl-6,7-dihydro-pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide and compound 15: (R*)-3,5-dichloro-pyridine-2-carboxylic acid [3-(4-amino-6-methyl- 6,7-dihydro-pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide and compound 16: (S *)-3 , 5 -dichloro-pyridine-2-carboxylic acid [3 -(4-amino-6-methyl-6, 7-dihydro- pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide3,5-Dichloro-2-pyridinecarboxylic acid (75.5 mg, 0.393 mmol) was added to a solution of 4-(4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholinium chloride (128 mg, 0.463 mmol) in MeOH (5 mL). The mixture was stirred at room temperature for 5 min. Then the mixture was cooled to 0 C and a solution of intermediate A49 (100 mg, 0.386 mmol) in MeOH (5 mL) was added. The mixture was warmed to room temperature and stirred for 4 hours. The mixture was treated with a saturated solution of Na2C03 and H20 and extracted with DCM. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; MeOH/DCM). The desired fractions were collected and the solvents evaporated in vacuo. The crude product was triturated with Et20, sonicated, filtered and dried in vacuo at 50C. The resulting compound was purified one addition time by flash column chromatography (silica gel; MeOH/DCM) to yield, after treatment with AcOEt and DIPE, compound 14 (95 mg, 57% yield) as a white solid. This racemic compound was then further purified by preparative SFC on Chiralcel OJ-H 5 muiotaeta (250 x 20 mm), mobile phase (0.3% iPr H2, 85% C02, 15% EtOH). The desired fractions for each enantiomer were collected and concentrated in vacuo to yield compound 15 (38 mg, 23% yield). 1H MR (400 MHz, CDC13) delta ppm 1.58 (s, 3 H), 2.52 (br. s., 2 H), 4.41 (br. d, J=13.2 Hz, 1 H), 4.62 (dd, J=13.2, 0.9 Hz, 1 H), 6.43 (d, J=2.1 Hz, 1 H), 7.08 (dd, J=11.7, 8.9 Hz, 1 H), 7.52 (d, J=2.1 Hz, 1 H), 7.81 (dd, J=6.9, 2.8 Hz, 1 H), 7.89 (d, J=2.1 Hz, 1 H), 7.94 (ddd, J=8.8, 4.1, 3.0 Hz, 1 H), 8.42 (d, J=2.1 Hz, 1 H), 9.71 (br. s., 1 H) and compound 16 (40 mg, 24% yield), for which the 1H NMR was in agreement with the one of compound 15.

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. 81719-53-1, 3,5-Dichloropyridine-2-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; GIJSEN, Henricus, Jacobus, Maria; VAN GOOL, Michiel, Luc, Maria; VEGA RAMIRO, Juan, Antonio; DELGADO-JIMENEZ, Francisca; WO2012/117027; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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 2; 2-(5-methoxy-pyridin-2-yl)-benzoic acid diethylamide; Under an argon atmosphere, a mixture of tripotassium phosphate (6.24 g) and water (15 ml) was added to a mixture of 2-chloro-5-methoxy-pyridine (2.05 g), 2-(diethylcarbamoyl)benzeneboronic acid (4.65 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride-dichloromethane complex (0.584 g) and toluene (30 ml), and the mixture was stirred at 80 C. for 2 hr. The reaction mixture was cooled to room temperature, water (20 ml), citric acid (2.2 g) and ethyl acetate were added and the mixture was stirred and filtered through celite. The filtrate was partitioned in a separatory funnel. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/2) to give a roughly purified product (1.144 g) of the title compound. This product was directly used for the next reaction without further purification.1H-NMR (CDCl3) delta: 8.33 (1H, d, J=2.9 Hz), 7.68 (1H, dd, J=7.7, 1.3 Hz), 7.60 (1H, d, J=8.6 Hz), 7.48-7.32 (3H, m), 7.25-7.15 (1H, m), 3.88 (3H, s), 3.32-2.78 (4H, m), 1.07 (3H, t, J=7.1 Hz), 0.81 (3H, t, J=7.2 Hz).

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 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Patent; JAPAN TOBACCO INC.; US2010/240634; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22918-01-0, Adding some certain compound to certain chemical reactions, such as: 22918-01-0, name is 2-Bromo-4-chloropyridine,molecular formula is C5H3BrClN, 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 22918-01-0.

Example 103a 2-Bromo-4-chloronicotinaldehyde 103a To a solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) in anhydrous tetrahydrofuran (40 mL) cooled at -70 C. was added the solution of lithium diisopropyl-amide (5.0 mL, 10.0 mmol, 2.0 M) over a period of 5 minutes and stirred at -70 C. for another 1h. Anhydrous DMF (1.3 g) was introduced over a period of 3 minutes and the mixture was stirred for another 30 minutes. It was then quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to afford 103a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO-d6) delta 10.21 (s, 1H), 8.52 (d, J=5.5 Hz, 1H), 7.79 (d, J=5.0 Hz, 1H).

According to the analysis of related databases, 22918-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14150-94-8 , The common heterocyclic compound, 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one, molecular formula is C6H5N3O5, 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.

General procedure: To a solution of dinitropyridone 1 (50.0 mg, 0.25 mmol) in ethanol (5 ml), were added enaminone 4a (38.8 mg, 0.25 mmol) and triethylamine (35mul, 0.25 mmol). The resultant mixture was heated at 100 C for 1 day. After evaporation, the residue was treated with column chromatography on alumina to afford 2-ethanoly-4-nitro-N-propylaniline (3a) (eluted with hexane/ethyl acetate = 8/2, 23.0 mg, 0.11 mmol, 43% (NMR Yield 63%)) as a yellow solid.

The synthetic route of 14150-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naito, Saki; Yokoyama, Soichi; Asahara, Haruyasu; Nishiwaki, Nagatoshi; Tetrahedron Letters; vol. 58; 50; (2017); p. 4699 – 4702;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem