Day: September 26, 2021

Electric Literature of 18368-64-4 ,Some common heterocyclic compound, 18368-64-4, molecular formula is C6H6ClN, 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.

2-Chloro-5-methylpyridine (10.03 g, 79 mmol), (3-chloro-4-methylphenyl)boronic acid (13.4 g, 79 mmol), and potassium carbonate (21.74 g, 157 mmol) were dissolved in the mixture of DME (150 ml) and water (20 ml) under nitrogen to give a colorless suspension. Pd(PPh3)4(0.909 g, 0.786 mmol) was added to the reaction mixture, then the reaction mixture was degassed and heated to 95° C. for 12 hrs. It was then cooled down to room temperature, separated organic phase and evaporated. The residue was subjected to column chromatography on silica gel column, eluted with heptanes/THF 9/1 (v/v), providing after crystallization from heptanes 10 g of 2-(3-chloro-4-methylphenyl)-5-methylpyridine (58percent yield) of white solid.

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. 18368-64-4, 2-Chloro-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Worldwide Show Corporation; Cai Ruiyi; Ji Zhiqiang; Ya Likexi·baolisuoweiqi·diyatejin; Xia Chuanjun; Lin Chun; Zeng Lichang; Wo Erte·yegeer; (191 pag.)CN107522748; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 81719-53-1, 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.81719-53-1, name is 3,5-Dichloropyridine-2-carboxylic Acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

3,5-dichloro-2-(chloromethyl)pyridine; [00376] To a 0 C solution of 5-chloropicolinic acid (5.00 g, 26.0 mmol) and N,N- dimethylformamide (1 drop) in dichloromethane (20 mL) was added oxalyl chloride (3.28 g, 26.0 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction was then cooled again to 0 C, after which methanol (10 mL) was added dropwise to the reaction mixture, and the reaction was allowed to stir at room temperature for one hour where it was shown as complete by LCMS analysis. The reaction mixture was washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and concentrated to afford methyl 3,5-dichloropyridine-2-carboxylate (5.36 g, 26.0 mmol, 100% yield ) as a white solid.[00377] To a 0 C solution of methyl 3,5-dichloropyridine-2-carboxylate (5.00 g, 24.3 mmol) in methanol (40 mL) was added sodium borohydride (1.80 g, 48.5 mmol), after which the reaction was warmed to room temperature and stirred at that temperature for two hours. The reaction mixture was then quenched by the addition of water (5 mL), concentrated to a residue, reconstituted in water (60 mL), extracted with ethyl acetate (2 x 60 mL), dried (magnesium sulfate), filtered and concentrated to afford (3,5-dichloropyridin-2-yl)methanol (2.90 g, 16.3 mmol, 67% yield ) as a viscous oil. This material was used in the subsequent step without any purification.[00378] To a 0 C solution of (3,5-dichloropyridin-2-yl)methanol (2.90 g, 16.3 mmol) in dichloromethane (50 mL) was added thionyl chloride (2.31 g, 19.6 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction mixture was washed by the addition of saturated sodium bicarbonate solution (1 x 40 mL) and the organic layer was separated, dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography using 9% ethyl acetate in hexanes to afford 3,5-dichloro-2- (chloromethyl)pyridine (2.40 g, 12.2 mmol, 75% yield) as an off-white solid. NMR (300 MHz, CDC13) delta (ppm): 8.36 (s, 1H), 7.56 (s, 1H), 4.66 (s, 2H).

Statistics shows that 81719-53-1 is playing an increasingly important role. we look forward to future research findings about 3,5-Dichloropyridine-2-carboxylic Acid.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-2-chloropyridine, 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, Product Details of 14432-12-3, blongs to pyridine-derivatives compound. Product Details of 14432-12-3

2-Chloro-pyridin-4-ylamine 1b* (3.2 g, 0.025 mol) and sodium acetate (4.1 g, 0.05 mol) were stirred in acetic acid (20 ml). A solution of iodine monochloride (4.1 g, 0.025 mol) in acetic acid (10 ml) was added and the reaction mixture was heated to 70 C for approximately 3 h (NB: solution at -50 C, brown colour faded and precipitate formed as the reaction proceeded). The reaction mixture was cooled to room temperature, then poured onto water (700 ml), and extracted with EtOAc. The organic layer was carefully washed with a solution of Na2CO3 followed by a solution of Na2S2O3, dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography using 10% EtOAc in DCM to yield 2-chloro-5-iodo-pyridin-4-ylamine 2b* (2.60 g, 40%). 1H NMR (400 MHz, CDCl3) delta (ppm): 8.34 (1 H, s), 6.63 (1 H, s), 4.78 (2 H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; ULLRICH, Axel; FALCENBERG, Mathias; WO2014/207260; (2014); 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.59786-31-1, name is Methyl 3-bromoisonicotinate, molecular formula is C7H6BrNO2, molecular weight is 216.03, as common compound, the synthetic route is as follows.Computed Properties of C7H6BrNO2

Step A Preparation of 3-(4-cyanobenzyl)pyridin-4-carboxylic acid methyl ester A solution of 4-cyanobenzyl bromide (625 mg, 3.27 mmol) in dry THF (4 mL) was added slowly over ~3 min. to a suspension of activated Zn (dust; 250 mg) in dry THF (2 mL) at 0° under an argon atmosphere. The ice-bath was removed and the slurry was stirred at room temperature for a further 30 min. Then 3-bromopyridin-4-carboxylic acid methyl ester (540 mg. 2.5 mmol) followed by dichlorobis(triphenylphosphine)nickel (II) (50 mg). The resultant reddish-brown mixture was stirred for 3 h at ~40°-45° C. The mixture was cooled and distributed between EtOAc (100 ml,) and 5percent aqueous citric acid (50 mL). The organic layer was washed with H2 O(2*50 mL), dried with Na2 SO4. After evaporation of the solvent the residue was purified on silica gel, eluding with 35percent EtOAc in hexane to give 420 mg as a clear gum. FAB ms (M+1)253.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59786-31-1, Methyl 3-bromoisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US5859012; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1219095-87-0, tert-Butyl (2-methylpyridin-3-yl)carbamate, 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, 1219095-87-0, blongs to pyridine-derivatives compound. Recommanded Product: 1219095-87-0

Tert-butyl N-(2-methylpyridin-3-yl)carbamate (5.41 g, 25.99 mmol) was dissolved in AcOH (100 mL). PtO2 (2.7 g) was added and the mixture was stirred overnight under H2 atmosphere (4 atm). The catalyst was filtered off, the solvent was evaporated and the residue neutralized with K2CO3 solid. The mixture was extracted with ethyl acetate (3×250 mL) and DCM (3×100 mL). The combined organic phases was concentrated under reduced pressure to give tert-butyl N-(2- methylpiperidin-3-yl)carbamate (7.0 g, quant. yield) as diastereoisomeric mixture. The diastereoisomeric mixture was purified by preparative chiral HPLC to give: tert-butyl N-[(2S,3S)-2-methylpiperidin-3-yl]carbamate (1.94 g, 9.05 mmol), tert-butyl N- [(2R,3R)-2-methylpiperidin-3-yl]carbamate (1.39 g, 6.48 mmol).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1219095-87-0, its application will become more common.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 79456-30-7, 3-Bromo-5-(trifluoromethyl)pyridin-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, Quality Control of 3-Bromo-5-(trifluoromethyl)pyridin-2-amine, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-5-(trifluoromethyl)pyridin-2-amine

To a solution of 2-amino-3-bromo-5-trifluoromethylpyridine from Example 1 (15 g) in dioxane/water/12N HCl (75 mL:75 mL:15.5 mL) at 0C was added a solution of sodium nitrite (10.54 g). The mixture was stirred for 3 h at r.t.. The mixture was poured into an ice bath and then neutralized with 10 N NaOH. The resulting solid was filtered and azeotroped with toluene. The resulting solid and POCl3 (14.5 mL) was heated at 80C for 3 h. The mixture was cooled to r.t., poured into an ice bath and then neutralized, first by the addition of 3 N NaOH followed by the addition of saturated sodium carbonate. The resulting mixture was extracted with CH2Cl2 and the combined organics were washed with brine, dried and concentrated. The title compound was obtained as a volatile liquid that was used without further purification in the next reaction.

The synthetic route of 79456-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA & CO.; EP1012142; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1232431-11-6, 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 1232431-11-6, name is 5-Bromo-4-methoxypyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

2-Amino-4-methoxy-5-bromopyridine (500 mg, 2.5 mmol) and 2- bromo- 4′- nitroacetophenone (1.21 g, 5.0 mmol) were dissolved in acetonitrile (40 mL) The solution was stirred at 85 degrees for 5h, After cooling to room temperature,A large number of yellow solid precipitation, filter, The filter cake was beaten with methanol (10 mL) Filter again The filter cake is vacuum dried, A yellow solid (360 mg, 42%) was obtained.

According to the analysis of related databases, 1232431-11-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Zhen, Changchun; Liu, Bing; Zhang, Weihong; Zhang, Yingjun; Long, Bohua; (59 pag.)CN104513257; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 942947-94-6, 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 942947-94-6, name is 5-Bromo-4-chloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromo-4-chloropyridin-2-amine (2.0g, 9.64mmol, l .Oeq), Di-tert-butyl dicarbonate (5.25g, 24.1mmol, 2.5eq) and triethyl amine (2.423g, 24.1mmol, 2.5eq) in tetrahydrofuran (lOmL) was added. Then 4-Dimethylaminopyridine (0.117g, 0.964mmol, 0.1 eq) was added and the reaction mixture was stirred at room temperature for 18h. After completion of reaction, reaction mixture was concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted in 10% ethyl acetate in hexane as eluent to obtain 186.3. (2.10g, 53.43%). MS(ES): m/z 408.69 [M+H]+

According to the analysis of related databases, 942947-94-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (2018); 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. 5350-93-6, name is 6-Chloropyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Chloropyridin-3-amine

6-chloropyridin-3-amine (40.0 g, 311 mmol) was dissolved in DMF (Volume: 534 mL) and treated with 1-iodopyrrolidine-2,5-dione (70.0 g, 311 mmol) in one portion. The reaction solution was stirred at room temperature under nitrogen overnight and quenched with water and extracted with EtOAc and Et2O. Organic layer was washed twice with brine and dried over sodium sulfate. DMF was removed on kugelrohr at 100 °C to afford ?90 g red solids. The crude was purified via column chromatography to give 6-chloro-2-iodopyridin-3-amine (57 g, 72percent yield).

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, 5350-93-6, 6-Chloropyridin-3-amine.

Reference:
Patent; Universal Display Corporation; Xia, Chuanjun; Joseph, Scott; EP2826781; (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. 131747-43-8, name is 2-Trifluoromethylnicotinic acid, molecular formula is C7H4F3NO2, 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. SDS of cas: 131747-43-8

2- [2-Chloro-4- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] phenyl-2,2-difluoro-1-methylethylamine 104 mg N, N -In a 2 ml solution of dimethylformamide, 65 mg of triethylamine, 5 mg of 4- (N, N-dimethylamino) pyridine and O- (benzotriazol-1-yl) -N, N, N ‘, N’-tetramethyluronium tetrafluoroborate 82 mg of lato, 3 mg of 4- (N, N-dimethylamino) pyridine and 49 mg of 2- (trifluoromethyl) nicotinic acid were added and stirred at room temperature for 12 hours. After completion of the reaction, 3 ml of water was added and extracted with ethyl acetate (5 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (gradient from 0:10 to 2: 8) to obtain 77 mg of the objective product as a colorless dendritic substance.

With the rapid development of chemical substances, we look forward to future research findings about 131747-43-8.

Reference:
Patent; Nissan Chemical Co., Ltd.; Iwasa, Motoyoshi; Yoshinaga, Yutaka; Mitsumori, Norihiko; Asahi, Miho; Uemura, Yuki; (97 pag.)JP2019/151593; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem