Pyridine-derivatives

Reference of 99368-67-9, 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. 99368-67-9, name is 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Reference Example 119 6-chloro-5-(trifluoromethyl)pyridine-3-amine; Reduced iron (1.3 g) and ammonium chloride (2.1 g) were added to water (40 mL), and the mixture was stirred at room temperature for 5 min. A solution of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (1.8 g) in methanol (40 mL) was added, and the mixture was stirred at room temperature for 1 hr. Reduced iron (2.3 g) was added, and the mixture was further stirred at the same temperature for 3 hr. The reaction mixture was filtered through celite, and celite was washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1?1:1) to give the title compound as a solid (yield 1.0 g, 65%). 1H-NMR (CDCl3) delta: 7.29 (1H, m), 7.99 (1H, m), 2H not detected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,99368-67-9, 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2007/60623; (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. 1603-41-4, name is 2-Amino-5-methylpyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 1603-41-4

3.40 mL of 50% sulfuric acid (v / v) was added to a 25 mL reaction flask followed by the addition of 1.00 g (10 mmol) of 2-amino-5-methylpyridine (Compound 1), the ice salt bath was cooled to below 10 C, After a few minutes, the reaction solution became milky white; and then slowly slowly adding 1.72 g (25 mmol) of a mixture of NaNO2 and 3 mL of H2O to form a brownish-colored irritating odor gas, and the reaction solution Into a pale yellow, with 10% dilute sulfuric acid to adjust the pH to 7-8, reflux stirring reaction about 20min, spin off most of the water, to which the appropriate amount of 300 mesh silica gel, spin dry, into the glass sand core funnel, The ester was filtered and the filtrate was spin-dried to obtain the crude product (Compound 3) which was used in the next step without purification.

The synthetic route of 1603-41-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Yin, Shu-Fan; Li, Yong; Cao, Tingting; Yang, Ziyao; (16 pag.)CN105998016; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6602-32-0, 2-Bromo-3-hydroxypyridine, 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 2-Bromo-3-hydroxypyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-3-hydroxypyridine

Diethyl azodicarboxylate (95 mL, 0.6 mol) was added dropwise to a stirred mixture of 2-bromo-3- hydroxypyridine (97 g, 0.55 mol), 3-buten-l-ol (47.7 mL, 0.55 mol), and PPh3 (175.3 g, 0.66 mol) in THF (970 mL) at 0C under a N2 atmosphere. The reaction mixture was warmed to 50C in an oil bath and stirred for 17.5 h. Reaction progress was monitored by TLC (15% EtOAc in hexane, UV active). The reaction mixture was cooled to ambient temperature and diluted with saturated NaHC03 solution (500 n L). The aqueous solution was extracted with EtOAc (1 L). The organic layer was dried over Na2S04 (200 g), and concentrated. The residual product was purified by column chromatography using 60-120 mesh, eluting with 5% EtOAc in hexane to afford the title compound as a pale yellow oil. MS (ESI) m/z; 228 (MH+).

The synthetic route of 6602-32-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NANT HOLDINGS IP, LLC; NANTWORKS, LLC; TAO, Chunlin; WANG, Qinwei; SOON-SHIONG, Patrick; (94 pag.)WO2017/24315; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 104408-23-3 ,Some common heterocyclic compound, 104408-23-3, molecular formula is C5H5Cl2N3, 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.

STR93 (Process (a) 16.9 g (0.1 mole) of ethyl ethoxymethylenecyanoacetate and 17.8 g (0.1 mole) of 3,5-dichloro-pyrid-2-ylhydrazine in 150 ml of ethoxyethanol are stirred at 80 C. for 5 hours and then at 120 C. for a further 2 hours. For working up, the solvent is removed in vacuo. 29.6 g (98% of theory) of 5-amino-1-(3,5-dichloro-pyrid-2-yl)-4-ethoxycarbonyl-pyrazole of melting point 98-101 C. are obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,104408-23-3, its application will become more common.

Reference:
Patent; Bayer Aktiengesellschaft; US4772312; (1988); A;,
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. 106877-33-2, name is 5-Amino-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H5F3N2

(1) Pyridine (2.9 mL) was added to a solution of 2-trifluoromethyl-5-aminopyridine (1.95 g) in chloroform (15 mL), the mixture was cooled in ice, and phenyl chloroformate (1.8 mL) was added thereto. The resulting mixture was stirred at room temperature overnight, and the reaction mixture was concentrated under reduced pressure. The residue was washed with isopropyl ether to afford phenyl[6-(trifluoromethyl)pyridin-3-yl]carbamate (2.16 g). (ESI pos.) m/z: 283 ([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, 106877-33-2, 5-Amino-2-(trifluoromethyl)pyridine.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; Moriya, Minoru; Ohta, Hiroshi; Yamamoto, Shuji; Abe, Kumi; Araki, Yuko; Sun, Xiang-Min; Wakasugi, Daisuke; US2013/331571; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1003-73-2, 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. 1003-73-2, name is 3-Methylpyridine 1-oxide, molecular formula is C6H7NO, 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.

Into the flask, 300 g of methylene chloride and 50 g of 3-picoline-N-oxide were added and the mixture was stirred and cooled to 5°C at a constant pressure.A dropping funnel was charged with a mixed solution of 240 g of 2,4,6-triisopropyl-3-benzoyl chloride and 200 g of methylene chloride and slowly added dropwise to the dichloromethane mixture of 3-picoline-N-oxide. In the dropping process, the reaction temperature is controlled at 5 to 10°C.The addition was completed within about 3 hours. The reaction was incubated for 2 hours and then warmed to 40°C overnight.After the end of the reaction, cool down to 5 ~ 10 °C, slowly add 200g of water, after desolvation steam distillation, collecting 100 ~At 102°C/760mmHg, the distillate was extracted with methylene chloride. After the aqueous layer was separated, 57.4 g of product was de-solvated.The content of 2-chloro-5-methylpyridine was 98percent, 2-chloro-3-methylpyridine was 0.5percent, and the yield of 2-chloro-5-methylpyridine was 96.2percent.

According to the analysis of related databases, 1003-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Hong Sun Biochemical Co., Ltd.; Chen Honglong; Mu Dengyou; Xue Yi; Chen Xinchun; Zhong Jingsong; Wang Fujun; Yang Cheng; (5 pag.)CN107721912; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 76469-41-5, 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. 76469-41-5, name is 2,3,5-Trifluoropyridine, molecular formula is C5H2F3N, 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 1(R)-(trans-(1-carbamoyl-4-adamantyl)) 3-(3,5-difluoropyridin-2-yloxy)pyrrolidine-1- carboxylateStep 1; To a stirred solution of (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate(1.1O g, 5.89 mmol) and 2,3,5-trifluoropyridine (0.86 g, 6.48 mmol) in dry THF (20 ml.) and dry DMF (4 ml_), at rt was added 60% NaH in oil (0.35 g, 8.84 mmol). The mixture was stirred in a 40 0C oil bath overnight, cooled to rt, diluted with ether (175 ml_), washed with water (25 mL) and brine (25 ml_), and dried over Na2SO4.Removal of the solvent left a dark oil (1.94 g) which was purified by chromatography on a 40-g silica cartridge eluted with a 0 – 100% EtOAc in hexanes gradient to afford (R)-tert-butyl 3-(3,5-difluoropyridin-2-yloxy)pyrrolidine-1- carboxylate (0.83 g, 47%). LC-MS Method 1 tR = 1.85 min, m/z = 301.

According to the analysis of related databases, 76469-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; LEFTHERIS, Katerina; SINGH, Suresh, B.; TICE, Colin, M.; YE, Yuanjie; ZHUANG, Linghang; WO2010/141424; (2010); 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.113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromonicotinaldehyde

To a mixture of 5-bromopyridine-3-carbaldehyde (XXXVIII) (6.00 g, 32.26 mmol, 1.0 eq), 3,3-difluoropyrrolidine (5.56 g, 38.71 mmol, 1.20 eq) and TEA (5.39 mL, 38.71 mmol, 1.2 eq) in DCE (200 mL) was stirred at room temperature for 30 mm, then added sodium triacetoxyborohydride (10.25 g, 48.38 mmol, 1.50 eq) in one portion at room temperature under N2. The mixture was stirred at room temperature for 6 h. TLC showed the reaction was complete. The reaction was quenched with iN NaOH (100 mL), extracted with DCE (100 mL x 2). The combined organic layers were washed with brine (100 mL), dried and concentrated. The residue was purified by silica gel chromatography (column height: 50 mm, diameter: 50 mm, 300-400 mesh silica gel, DCMIMeOH=3 0/1 -*20/1) to give 3 -bromo-5 -((3,3 -difluoropyrrolidin- 1- yl)methyl)pyridine (XL): Yellow oil (8.00 g, 28.9 mmol, 89.5% yield). ?H NMR (CDC13, 400 MHz) ppm 2.30 (spt, J=7.2Hz. 2H), 2.75 (t, J=6.8Hz, 2H), 2.91 (t, J13.2Hz, 2H), 7.85 (s, 1H), 8.45 (s, 1H), 8.59 (d, J=2Hz, 1H); ESIMS found for C,0H,,BrF2N2 m/z 277.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-81-3, 5-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (271 pag.)WO2017/24026; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 107504-08-5 , The common heterocyclic compound, 107504-08-5, name is 5-Fluoro-2-picolinic acid, molecular formula is C6H4FNO2, 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.

To a suspension of the aniline compound 1-3 (0.17 g, 0.57 mmol) and 0.104 g (0.74 mmol) of 5-fluoropyridine-2-carboxylic acid in 5 mL of dichloromethane were added 0.289 g (1.14 mmol) of BOPC1 and 0.22 g (1.7 mmol) of diiosopropylethylamine. The solution was stirred at room temperature for 40 min, and quenched with water (10 mL). The mixture was extracted with two 30 mL portions of dichloromethane. The combined organic extracts were concentrated; the residue was purified by flash chromatography (12 g of Si02: 0 to 4% MeOH in CH2C12 plus 1% NH4OH) to give a free base, which was treated with HCl in ether to form the salt l-4a (0.192 g, 74%). LCMS for l-4a (conditions A): tR = 1.94 min, m/e = 423 (M+H).

The synthetic route of 107504-08-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WU, Wen-Lian; BURNETT, Duane A.; STAMFORD, Andrew W.; CUMMING, Jared N.; BENNETT, Chad Edward; GILBERT, Eric J.; PENG, Xuanjia; SCOTT, Jack D.; YU, Younong; WO2012/139425; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89182-17-2, 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. 89182-17-2, name is 6-Chloro-3,4-pyridinediamine, molecular formula is C5H6ClN3, 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.

Synthesis of (6-chloro-1H-imidazo[4,5-c]pyridin-2-yl)benzylamine A solution of benzylthioisocyanate (7.0 mL, 53.1 mmol) and 6-chloro-pyridine-3,4-diamine (7.6 g, 53.1 mmol) in CHCl3 (110 mL) was heated at 50 C for 12 h. After cooling to ambient temperature, the reaction mixture was treated with EDC (12.2 g, 63.7 mmol) and Et3N (8.9 mL, 63.7 mmol). The reaction mixture was then stirred at room temperature for additional 18 h. CHCl3 (110 mL) was added to the reaction mixture, followed by water (110 mL) and the organic phase was separated. The aqueous phase was re-extracted with CHCl3 (2 x 150 mL) and the combined organic layers were washed with brine (50 mL). The organic layers were dried over Na2SO4, then concentrated in vacuo and purified by column chromatography on silica gel (AcOEt ? 5% MeOH/AcOEt, then 90% DCM/MeOH) to give the product as a brown semi-solid. The solid was further purified by trituration with ice cold iPr2O ether to give the product as an off white solid, which was used without further purification (3.00 g, 22%). LC-MS: Rt = 2.31 min; [M+H]+ 259/261.

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 89182-17-2, 6-Chloro-3,4-pyridinediamine.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel (Prof. Dr.); Falcenberg, Mathias (Dr.); EP2818472; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem