Tag: M.W:100-200

Electric Literature of 51173-05-8, Adding some certain compound to certain chemical reactions, such as: 51173-05-8, name is 5-Fluoro-2-hydroxypyridine,molecular formula is C5H4FNO, 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 51173-05-8.

To a solution of 5-fluoro-2-hydroxypyridine (200 mg, 1.77 mmol) in concentrated sulfuric acid (900 mul) was added, dropwise over 15 minutes, a premixed solution of concentrated sulfuric acid (900 mul) and fuming nitric acid (170 mul). The internal temperature rose by up to 280C. The reaction mixture was then heated at 650C for 2.5 hours. The cooled mixture was poured onto ice-water, and the pH of the mixture was adjusted to 2.5 with sodium carbonate. It was then extracted with ethyl acetate (2 x 25 ml). The aqueous layer was concentrated and extracted again with a mixture of tetrahydrofuran (25 ml) and ethyl acetate (25 ml). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the title compound (112 mg, 40%) as a solid. 1H NMR (400MHz, DMSO-D6): delta 8.22 (dd, 1 H), 8.60 (dd, 1 H); LRMS APCI” m/z 157 [M-H]’.

According to the analysis of related databases, 51173-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2006/114706; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6515-09-9, 2,3,6-Trichloropyridine, 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 2,3,6-Trichloropyridine, blongs to pyridine-derivatives compound. Quality Control of 2,3,6-Trichloropyridine

Example 11 Compound No. 37 in Table 1 [0087] 2-chloro-5-ethylaminomethylthiazole, 18.6 g of 2,3,6-trichloropyridine, 30.0 g of potassium carbonate and 200 mL of N,N-dimethylformamide (DMF) were added in a 500 mL single neck flask equipped with a magnetic stirrer. After stirred at reflux temperature for 4 to 6 hours, the reaction mixture was extracted with ethyl acetate, the organic layer was separated while the aqueous layer was extracted with ethyl acetate twice. The organic phases were combined, and dried over anhydrous sodium sulfate after washed with an iced aqueous sodium chloride solution twice, then remove the solvent under reduced pressure to obtain 25.0 g of crude product which was purified by a silica gel column chromatography using a petroleum ether/ ethyl acetate (20/1) as an eluent to obtain 13.0 g of 6-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-chloropyridin-2-amine, having the content 91.0%, as a yellow viscous liquid, and rod-like crystals were generated after standing, m.p.: 95.8-96.8 ? GC-MS (M+) (EI, 70 eV, m/z) calc: 321; found: 321; 1H NMR (CDCl3/TMS, 300 MHz) delta (ppm) 1.179 (t, J=7.2 Hz, 3H, CH3), 3.413 (q, J=7.2 Hz, 2H, CH2), 4.726 (s, 2H, CH2), 6.378 (d, J=8.7 Hz, 1H, Py H), 7.447 (d, J=8.7 Hz, 1H, Py H), 7.497 (s, 1H, Thiazole-H).

The synthetic route of 6515-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Aiping; Wang, Xiaoguang; He, Lian; Ou, Xiaoming; Liu, Minhua; Chen, Ming; Liu, Xingping; Tang, Ming; Ren, Yeguo; Chen, Haobin; US2015/51402; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71670-70-7 ,Some common heterocyclic compound, 71670-70-7, molecular formula is C7H9Cl2N, 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.

Step 1: 3-[1-(4-Bromo-benzyl)-3-tert-butylsulfanyl-5-(6-fluoro-quinolin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester To 3-[1-(4-Bromo-benzyl)-3-tert-butylsulfanyl-5-hydroxy-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester (C-3; 0.25 g, 0.48 mmol) in DMF (2 mL) was added 2-chloromethyl-5-methyl-pyridine hydrochloride (0.13 g, 0.72 mmol), Cs2CO3 (0.39 g, 1.21 mmol), and catalytic tetrabutylammonium iodide. The reaction was stirred at room temperature overnight, after which LCMS showed the reaction was complete. The reaction mixture was partitioned between EtOAc and water, the aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The crude material was purified on silica gel (0 to 15% EtOAc in hexanes) to give an additional the desired product (E-1, 0.30 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71670-70-7, its application will become more common.

Reference:
Patent; Amira Pharmaceuticals, Inc.; US2007/105866; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 112110-07-3 ,Some common heterocyclic compound, 112110-07-3, molecular formula is C6H5F3N2, 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.

Dissolve the amine obtained in Step 2 (380 mg, 2.35 mmol), pyridine (371 mg, 4.7 mmol) in DCM (8 mL), cool to 0 C. in ice bath. Add slowly phenyl chloroformate (403 mg, 2.35 mmol). After addition, stir the reaction at 0-5 C. for 2 hrs. Pour the mixture into water (50 mL), adjust pH to neutral with 1M HCl solution, extract with EtOAc (15 mL*3). Combine the organic layers; wash with brine (100 mL), dry over anhydrous Na2SO4, and concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc_PE=15:85) affords the target compound (390 mg, 59%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,112110-07-3, its application will become more common.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 92992-85-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 92992-85-3 as follows.

To 2-bromo-3,5-dimethylpyridine (204 muL) were added (R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester (350 muL),tris(dibenzylideneacetone)dipalladium(0)(73.8 mg),rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (100.4 mg),tert-butoxy sodium (232.4 mg) and toluene (4 mL) and the mixture was stirred at 120c for 7 hr. The reaction mixture was cooled and filtered through celite. The filtrate was concentrated and the obtained residue was purified by column chromatography (hexane:ethyl acetate)to give the title compound (459 mg). MS(APCI)m/z:292 (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,92992-85-3, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); 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 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Imidazo[1,2-a]pyridine-2-carboxylic acid

To a solution of 23-1 (O.lg, 0.7mmol) in EtOH (15ml) in a dried flask was added Pt2O (O. Ig, 0.4mmol). The reaction mixture was placed under a nitrogen atmosphere and was subsequently evacuated. This was repeated 3 times before placing the reaction mixture under an atmosphere of hydrogen. After 3h the reaction mixture was filtered through celite. Upon solvent removal the desired product 23-2 was obtained as an off-white powder. MS calculated M+H: 167.2, found 167.1

With the rapid development of chemical substances, we look forward to future research findings about 64951-08-2.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
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 10273-89-9, name is 2-(o-tolyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-(o-tolyl)pyridine

General procedure: A 10 mL Schlenk tube was charged with CoBr2 (6.6 mg, 0.03mmol), 1,3-diisopropyl-1H-benzimidazol-3-ium bromide (L4; 8.5mg, 0.03 mmol), 4-methoxy-N-[(1E)-1-phenylethylidene]aniline(1a, 67.6 mg, 0.30 mmol), 1-chlorooctane (2a, 76.5 muL, 0.45 mmol), and THF (0.69 mL). A 1.92 M solution of t-BuCH2MgBr inTHF (0.31 mL, 0.60 mmol) was added dropwise at 0 C, and themixture was stirred at r.t. for 6 h. The reaction was quenched by theaddition of 3 M aq HCl (1.0 mL), and the mixture was stirred at r.t.for 1 h, then extracted with EtOAc (3 × 10 mL). The organic layerswere combined, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by chromatography [silicagel, hexane-EtOAc (40:1)].

With the rapid development of chemical substances, we look forward to future research findings about 10273-89-9.

Reference:
Article; Gao, Ke; Yamakawa, Takeshi; Yoshikai, Naohiko; Synthesis; vol. 46; 15; (2014); p. 2024 – 2039;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 33252-28-7, 6-Chloronicotinonitrile, 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 33252-28-7, blongs to pyridine-derivatives compound. Product Details of 33252-28-7

6-(5-methyl-1H-1,2,4-triazol-1-yl)pyridine-3-carboxylic acid 2-Chloro-5-cyanopyridine (1.5 g) is dissolved in hydrazine (6 mL) at r.t. and an exothermic reaction occurs and a solid precipitate forms. Water is added and the solid is filtered off washing with water and is dried by suction to give the hydrazine intermediate. The hydrazine is suspended in acetic acid (7 mL) and N-((dimethylamino)methylene)acetamide [made from acetamide and DMF-dimethylacetal by procedure in US2007/0111984A1] (700 mg) is added and heated at 90 C. for 5.5 h. Additional N-((dimethylamino)methylene)acetamide (200 mg) is added and the mixture is heated at 90 C. for 3 h. After cooling and concentrating the residue is purified by chromatography on silica gel eluting with 0% to 100% ethyl acetate/hexane to give the intermediate nitrile. The nitrile is dissolved in MeOH (10 mL) and 4 M NaOH (2 mL) is added and heated at 65 C. for 16 h. The mixture is neutralized with 6 M HCl, concentrated, and then acidified to pH 2 with 6 M HCl. The precipitate is filtered off washing with water and dried by suction to give the title compound. LC (method 20): tR=1.53 min; Mass spectrum (APCI): m/z=205 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-28-7, 6-Chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil J.; HARRIOTT, Nicole; US2013/143892; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59942-87-9 ,Some common heterocyclic compound, 59942-87-9, molecular formula is C7H6N2O, 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 13: Synthesis of 4-(2-(pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine To a solution of pyrazolo[1 ,5-a]pyridin-2-ol (120 mg, 0.89 mmol) in 4 ml_ of anhydrous DMF, were added K2C03 (270 mg, 1 .95 mmol), 4-(2-chloroethyl)morpholine hydrochloride (183 mg, 0.98 mmol) and Nal (134 mg, 0.89 mmol) and the mixture heated to 80 5C for 18 h under nitrogen. The solvent was evaporated under reduced pressure and the residue poured into a mixture of EtOAc and water, to afford after drying and evaporation of organic layers, 1 12 mg of an oil that was purified by silica gel flash chromatography with EtOAc/MeOH (9:1 ) as eluent to afford 57 mg of 4-(2- (pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine. 40 mg (0.43 mmol) of anhydrous oxalic acid in 0.5 ml_ of acetone were added to a solution of 98 mg of 4-(2- (pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine base oil in 0.5 ml_ of acetone. The solid is filtered and washed with diethyl ether to give 133 mg (90%). 1 H NMR (DMSO) delta ppm: 8.46 (d, J = 6.9 Hz, 1 H), 7.46 (d, J = 8.9 Hz, 1 H), 7.26 – 7.09 (m, 1 H), 6.74 (td, J = 6.9, 1 .4 Hz, 1 H), 6.00 (s, 1 H), 4.41 (t, J = 5.3 Hz, 2H), 3.74 – 3.60 (m, 4H), 3.07 (t, J = 5.2 Hz, 2H), 2.92 – 2.66 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59942-87-9, its application will become more common.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ FERNANDEZ, Jose Luis; CUBERES ALTISENT, Mª Rosa; WO2013/124341; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13958-93-5 ,Some common heterocyclic compound, 13958-93-5, molecular formula is C6H3Cl2NO2, 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 8 difluorocyclobutanecarboxamide.2HCI; 3,5-Dichloroiso?icotinic acid (84mg, 0.4mmol), the compound of Preparation 42 (150mg, 0.3mmol), 3- (diethoxyphosphoryloxy)-1 ,2,3-benzotriazin-4(3H)-one (132mg, 0.4mmol) and triethylamine (0.16mL, 1.2mmol) were dissolved in dichloromethane and stirred at room temperature for 24hours. The reaction was quenched by the addition of saturated sodium hydrogen carbonate solution and extracted using dichloromethane. The combined organic extracts were concentrated in vacuo to give the crude product. The crude mixture was purified by column chromatography on silica gel using dichloromethane-.methanol EPO (100:0 to 90:10) as eluent. The resulting product was then dissolved in dichloromethane (5mL) and treated with 2M hydrochloric acid in diethyl ether (5mL), the solvents were removed in vacuo to give 43mg of title compound as a white solid.1H NMR (400MHz CDCI3) delta 0.95 (3H, s), 1.20-1.85 (9H, m), 1.85-2.00 (1 H, m), 2.05-2.30 (2H, m), 2.45(1 H, bs), 2.70-3.10 (6H, m), 3.25-3.50 (2H, m), 4.05-4.20 (1H, m), 4.40-4.65 (2H, m), 7.10-7.40 (5H1 m),8.50 (2H, bs).LRMS: m/z APCI+579[MH+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13958-93-5, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2006/77499; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem