Day: March 10, 2021

Reference of 944937-53-5, 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.944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 ¡Á 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

Statistics shows that 944937-53-5 is playing an increasingly important role. we look forward to future research findings about 6-Bromo-1H-pyrrolo[3,2-b]pyridine.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 2402-77-9, Adding some certain compound to certain chemical reactions, such as: 2402-77-9, name is 2,3-Dichloropyridine,molecular formula is C5H3Cl2N, 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 2402-77-9.

Reaction performed under nitrogen atmosphere. To a solution of n-butyllithium (27.6 ml, 69 mmol, 2.5 M in hexanes) in dry Et2O (150 ml) cooled at -78 0C, was added 2,2,6,6-tetramethylpiperidine (11.64 ml, 69 mmol) dropwise. The resulting reaction mixture was stirred at -78 0C for 10 min. and then a solution of 2,3-dichloropyridine (10 g, 67.57 mmol) in dry THF (75 ml) was added dropwise. The mixture was stirred at -78 0C for 30 minutes and then a solution of iodine (25.38 g, 100 mmol) in dry THF (75 ml) was added. The mixture was allowed to warm to room temperature overnight, quenched with Na2S2O3 (aqueous sat. solution) and extracted twice with EtOAc. The combined organic extracts were washed with NaHCO3 (aqueous sat. solution), dried (Na2SO4) and evaporated in vacuo. The crude residue was precipitated with heptane, filtered off and dried to yield compound D16 (8.21 g, 44%) as a pale cream solid. LCMS: MW (theor): 273; [MH+]: did not ionise; RT (min): 2.73 (Method 21).

According to the analysis of related databases, 2402-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC.; ADDEX PHARMA S.A.; WO2009/62676; (2009); A2;,
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. 55934-00-4, name is 3,4-Dichloropyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

General Procedure: To a 50 mL round bottom flask equipped with a stir bar were added 3,4- dichloropyridine (0.70 g, 4.73 mmol), piperazine-1-carboxylic acid tert-butyl ester (0.86 g, 4.73 mmol), copper powder (36 mg, 0.57 mmol), potassium carbonate (0.65 g, 4.73 mmol) and N,N-dimethylfbrrnamide (10 mL). The reaction mixture was stirred at 110 C overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and sequentially washed with water (50 mL), saturated aqueous sodium bicarbonate (50 mL), water (50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vauo. The crude residue was purified on silica gel using hexanesrethyl acetate = 80:20 to 50:50 in a gradient fashion, to give the desired product as a yellow solid (404 mg, 29 %). 1H NMR (300 MHz, CDCl3): delta 8.30 (bd, 2H), 6.74 (d, IH), 3.52 (m, 4H), 3.07 (m, 4H), 1.4 (s, 9H).

The synthetic route of 55934-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2007/87135; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 947248-68-2, 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. 947248-68-2, name is 6-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine. A new synthetic method of this compound is introduced below.

c) 2,6-Dibromo-[ 1 ,2,4] triazolo[ 1 ,5-a]pyridineA mixture of 6-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-amine (20.86 g, 97.9 mmol), sodi- um nitrite (67.6 g, 979 mmol) and benzyltriethylammonium bromide (53.3 g, 196 mmol) in bromoform (1.47 kg, 508 ml, 5.81 mol) was stirred for 30 minutes at 25 C. Then dichloroacetic acid (25.3 g, 16.2 ml, 196 mmol) was added and the mixture was stirred for 20 hours at 25 C under exclusion of light. 600 ml of water were added to the mixture and stirred for 30 minutes. The mixture was diluted with water and dichloromethane, filtrated over dicalite and the filtrate extracted 3 times with dichloromethane. The organic layers were combined, washed with water, dried over magnesium sulfate, filtrated and evaporated to dryness under reduced pressure. The crude material was purified by flash chromatography in 2 portions over 2 x 70 g silica columns using dichloromethane/methanol 5 % as eluent, affording 2,6-dibromo-[l,2,4]triazolo[l,5- a]pyridine (7 g, 26%) as light brown solid. Mp.: 201C. MS: m/z=277.7/279.9 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,947248-68-2, 6-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; WO2013/41472; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 100-70-9, 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. 100-70-9, name is Picolinonitrile, molecular formula is C6H4N2, 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.

Reference Example A8; Under nitrogen atmosphere, a solution of anhydrous cerium chloride (5.0 g) in tetrahydrofuran (40 mL) was stirred at room temperature overnight. To the reaction mixture was added dropwise a solution of 1.04M methyl lithium in diethylether (19 mL) under cooling in a dry ice/acetone bath over a period of 20 minutes. The mixture was stirred at the same temperature for 30 minutes, and to the reaction mixture was added dropwise a solution of 2- cyanopyridine (685 mg) in tetrahydrofuran (1 mL) . After warming to room temperature over a period of 5 hours, to the reaction mixture was added an aqueous 28% ammonia solution (12.5 mL) under ice-cooling. The mixture was filtered through Celite to remove precipitates. The filtrate was dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to give 1-methyl-l- (2- pyridyl) ethylamine (863 mg) as a brown oil. MS(APCI)m/z; 137 [M+H]+

According to the analysis of related databases, 100-70-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; WO2008/4698; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6345-27-3 , The common heterocyclic compound, 6345-27-3, name is Isonicotinimidamide hydrochloride, molecular formula is C6H8ClN3, 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: A 20 mL of Schlenk tube equipped with a stir bar was charged with benzyl bromides (0.12 mmol), aryl amidines (0.1 mmol), S8 (0.1 mmol), LiOtBu (0.4 mmol). The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 140 ¡ãC for 12 h in oil bath. Then the solvent was concentrated in vacuum and the residue was purified by flash column chromatography on silica gel with petroleum ether-EtOAc as the eluent to give the desired product.

The synthetic route of 6345-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Zhen; Liu, Miaochang; Sun, Song; Yao, En; Liu, Suqin; Wu, Zhiwen; Yu, Jin-Tao; Jiang, Yan; Cheng, Jiang; Tetrahedron Letters; vol. 58; 26; (2017); p. 2571 – 2573;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 108-96-3, Adding some certain compound to certain chemical reactions, such as: 108-96-3, name is Pyridin-4(1H)-one,molecular formula is C5H5NO, 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 108-96-3.

I Oa. 3,5-Diiodo-pyridin-4-ol Into a 3 L three necked round bottom flask I ,4-dihydropyridin-4-one (50.0 g, 0.50 mol) and N-iodosuccinimide (232 g, 1.00 mmol) were suspended inacetonitrile (1 L). The reaction mixture was refluxed for 3h. The mixture was cooled down with an ice bath and then filtered and washed with acetonitrile (150 mL). The light yellow solid was dried at 60C under reduced pressure for 15 hr to obtain 165 g (95 %) of the title compound as a light yellow solid. LC/MS (Method B): Rt 1.34 mm, (M+H) 348.

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. 108-96-3, Pyridin-4(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, Kai; STIEBER, Frank; CALDERINI, Michel; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; (127 pag.)WO2015/144290; (2015); A1;,
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. 7379-35-3, name is 4-Chloropyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H5Cl2N

Step 1: LDA (0.11 mmol) was added to 4-chloropyridine 1 (15 g, 0.1 mol) in THF (250 mL) dropwise at -60C and stirred at this temperature for 1 h. Then, DMF (9.3 mL, 0.12 mol) was added and stirred at room temperature overnight. The product was extracted with EA from water. The combined organic layer was dried(Na2SCU), filtered and concentrated. The residue was purified by column chromatography (P.E/EA 10:1) to afford 4.6 g white solid, yield 65%. 1HNMR (400MHz, CDCl3): 10.51 (s, 1H), 9.05 (s, 1H), 8.08 (d, 1H), 7.45 (d, 1H).

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, 7379-35-3, 4-Chloropyridine hydrochloride.

Reference:
Patent; ACHAOGEN, INC.; WO2009/55696; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, 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, 6980-08-1, blongs to pyridine-derivatives compound. Application In Synthesis of 4-Chloro-3-nitropyridin-2-amine

Step 1 A solution of 2-chloro-3-nitro-pyridin-4-amine (LXXXI) (1.5 g, 8.64 mmol), 2-(5-fluorothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (XCIV) (2.96 g, 12.96 mmol), Pd(dppf)Cl2 (632 mg, 0.86 mmol) and Cs2CO3 (5.63 g, 17.29 mmol) in dioxane (30 mL) and H2O (5 mL) was de-gassed and then heated to 100 C. under N2 for 3 h. TLC (PE:EtOAc=1:1) showed the starting material was consumed completely. The mixture was concentrated in vacuum to give a residue, which was purified by column chromatography to afford 4-(5-fluorothiophen-2-yl)-3-nitropyridin-2-amine (XCV) (800 mg, 3.34 mmol, 38.7% yield). ESIMS found C9H6FN3O2S m/z 240.1 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6980-08-1, its application will become more common.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98198-48-2, 2-Amino-5-bromo-4-methylpyridine, 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: 2-Amino-5-bromo-4-methylpyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Amino-5-bromo-4-methylpyridine

b) Ethyl (E)-3-(6-amino-4-methylpyridin-3-yl)acrylate To a stirred solution of 2-amino-5-bromo-4-methylpyridine (10 g, 54 mmole) in propionitrile (50 mL) was added ethyl acrylate (17 mL, 157 mmole), DIEA (19 mL, 106 mmole), palladium(II) acetate (0.61 g, 2.7 mmole) and tri-o-tolylphosphine (1.64 g, 5.4 mmole). The reaction was purged with argon and heated at reflux for 6 hr, then was cooled to RT and concentrated to dryness under vacuum. The resulting residue was taken up in ethyl acetate and filtered through a pad of silica gel. The filtrate was concentrated and the remaining residue was triturated with 1:1 Et2O/petroleum ether (50 mL), filtered, and dried under vacuum to give the title compound (6.50 g, 59%) as a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1 H), 7.66 (d, J = 16.0 Hz, 1 H), 6.40 (br s, 2 H), 6.32 (d, J. = 16.0 Hz, 1 H), 6.28 (s, 1 H), 4.15 (q, 2 H), 2.24 (s, 3 H), 1.24 (t, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98198-48-2, 2-Amino-5-bromo-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Affinium Pharmaceuticals, Inc.; EP1226138; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem