Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 1628-89-3, 2-Methoxypyridine, 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, 1628-89-3, blongs to pyridine-derivatives compound. COA of Formula: C6H7NO

A solution of 2-methoxy-pyridine (100 g, 0.92 mole), NBS (180 g, 1.0 mole) inacetonitrile (1. OL) was stirred at reflux for 21 h. TLC showed that the reaction wascomplete. The reaction mixture was cooled to room temperature and concentrated. 900ml solvent was collected. The resulting suspension was filtered and washed with n-hexane (400mL). The filtrate was concentrated again to afford crude product. The cmde product was distilled at reduced pressure (30C[-0.3mmHg) to afford the title compound as a clearoil (146 g, 84%). LCMS (m/z): 190.0 [M+1f ?H NMR (400 MHz, CDC13): oe 3.90 (s,3H), 6.65 (d, J= 8.8 Hz, 1H), 7.62 (dd, J= 8.8 Hz, 2.4Hz, 1H), 8.19 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1628-89-3, its application will become more common.

Reference:
Patent; CURIS, INC.; FATTAEY, Ali; RHYASEN, Garrett, W.; (61 pag.)WO2018/85342; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1480-65-5 ,Some common heterocyclic compound, 1480-65-5, molecular formula is C5H3ClFN, 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.

A solution of 5-chloro-2-fluoropyridine (500 mg, 3.80 mmol), DIEA (1.5 g, 11.61 mmol), methyl 2-(piperidin-4-yl)acetate (599 mg, 3.81 mmol) in DMSO (10 mL) was stirred for 16 h at 90 ¡ãC under N2. The resulting solution was extracted with 2×50 mL of EtOAc, and the combined organic layers were concentrated under vacuum and purified with silica gel chromatography using EtOAc / hexane (1/1) to afford 700 mg (69percent) of the title compound as an off-white solid. -MS (ES, m/z): 268.9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1480-65-5, its application will become more common.

Reference:
Patent; CENTAURUS THERAPEUTICS; ROMERO, Donna L.; MCCALL, John M.; BLITZER, Jeremy; (118 pag.)WO2018/112077; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 20260-53-1 , The common heterocyclic compound, 20260-53-1, name is Nicotinoyl chloride hydrochloride, molecular formula is C6H5Cl2NO, 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 solution of nicotinyl chloride hydrochloride (3.16 g, 17.76 mmol) and LI-2c (3 g, 11.84 mmol) in THF (50 mL) was added TEA (8.3 mL, 59.2 mmol) and stirred overnight at RT. After usual aqueous work-up and chromatographic purification, 4.14 g (97%) of LI-2c-nicotinate ester was obtained as a colorless oil. 1H NMR (CDCl3, 300 MHz): delta 1.43 (s, 9H), 2.82 (t, 2H, J=6.31 Hz), 3.42-3.48 (q, 2H), 4.62 (t, 2H, J=6.59 Hz), 7.29-7.33 (m, 1H), 8.30 (d, 1H, J=7.95 Hz), 8.78 (dd, 1H, J=4.86, 1.72 Hz), 9.23 (d, 1H, J=2.13 Hz). MS: m/z 358 [M+H]+, 381 [M+Na]+, 739 [2M+Na]+.

The synthetic route of 20260-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Satyam, Apparao; US2006/46967; (2006); 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 113118-81-3, name is 5-Bromonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Bromonicotinaldehyde

To a mixture of 5-bromopyridine-3-carbaldehyde (LIII) (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 min, 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 hours. TLC showed the reaction was complete. The reaction was quenched with 1N NaOH (100 mL), extracted with DCE (100 mL¡Á2). 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, DCM/MeOH=30/1?20/1) to give 3-bromo-5-((3,3-difluoropyrrolidin-1-yl)methyl)pyridine (LV): Yellow oil (8.00 g, 28.9 mmol, 89.5% yield). 1H NMR (CDCl3, 400 MHz) delta ppm 2.30 (spt, J=7.2 Hz, 2H), 2.75 (t, J=6.8 Hz, 2H), 2.91 (t, J=13.2 Hz, 2H), 7.85 (s, 1H), 8.45 (s, 1H), 8.59 (d, J=2 Hz, 1H); ESIMS found for C10H11BrF2N2 m/z 277.0 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 113118-81-3.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (387 pag.)US2016/75701; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1462-86-8, 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.1462-86-8, name is 3-Aminopicolinic acid, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

General procedure: Method B: To a solution of 3-aminopyridine-2-carboxylic acid (2.74 g, 20 mmol) in anhydrous DMF (100 mL) was added EDC (4.2 g, 22 mmol), HOBt (2.97 g, 22 mmol) and triethylamine (8.2 mL, 60 mmol). alpha-Amino acid methyl ester (22 mmol) was added, and the reaction mixture was stirred overnight. Water (100 mL) was added, and the mixture was extracted with methylene chloride (4 ¡Á 100 mL), dried over MgSO4 and concentrated. The compound was purified by silica gel chromatography to give the oil-like open product 6; this was then dissolved in THF (125 mL) under argon. Sodium hydride (0.93 g, 60% dispersion in oil, 26.8 mmol) was added, and the reaction mixture was stirred overnight. Water (5 mL) was carefully added, and the resulting white precipitate was collected. The precipitate was dissolved in ethyl acetate (200 mL), washed with water (50 mL) and brine (50 mL), dried over MgSO4 and concentrated to give product 8.

Statistics shows that 1462-86-8 is playing an increasingly important role. we look forward to future research findings about 3-Aminopicolinic acid.

Reference:
Article; El Bouakher, Abderrahman; Laborie, Helne; Aadil, Mina; El Hakmaoui, Ahmed; Lazar, Said; Akssira, Mohamed; Viaud-Massuard, Marie-Claude; Tetrahedron Letters; vol. 52; 39; (2011); p. 5077 – 5080;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6283-81-4 ,Some common heterocyclic compound, 6283-81-4, molecular formula is C10H11NO3, 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.

A mixture of 196 mg of ethyl nicotinoylacetate and 192 mg of ethyl 6-aminocaproate is heated at 120-130 under nitrogen for 18 hours. The product is purified by preparative TLC (silica gel; chloroform, ethyl acetate 9.1) to yield ethyl beta-(3-pyridyl)-beta-(5-ethoxycarbonylpentylamino)acrylate;Rf =0.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6283-81-4, its application will become more common.

Reference:
Patent; Ciba-Geigy Corporation; US4478842; (1984); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6419-36-9, 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. 6419-36-9, name is 2-(Pyridin-3-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

The 3-pyridine acetic acid hydrochloride obtained in step (4), phosphorous acid and chlorobenzene were added to a three – necked flask, and the amount ratio of the of the 3-pyridine acetic acid hydrochloride to phosphorous acid was 1:25 . The amount of chlorobenzene used was calculated according to the addition of 0.1 moles of 3-pyridine acetic acid hydrochloride per 100 mL of chlorobenzene. Reaction was stirr heated to reflux, dropping addition phosphorus trichloride, according to the ratio of the amount of 3-pyridine acetic acid hydrochloride and phosphorus trichloride was 1: 3 drop of phosphorus trichloride. After completion of the dropwise addition, the mixture was further refluxed for 7.5 hours, cooled to room temperature, and dumped chlorobenzene. The concentrated hydrochloric acid having a mass fraction of 37.5% and water was added to the residue , and 100 mL of concentrated hydrochloric acid and 50 mL of water were added per 100 mL of chlorobenzene, and refluxed for 7 hours. The activated charcoal was decolorized and filtered. The filtrate was concentrated to dryness under reduced pressure. The residue was added to absolute ethanol and 100 mL of anhydrous ethanol was added per 100 mL of chlorobenzene, precipitated large solid precipitation, and crushed into a powder. filtered, filter cake recrystallization with water, then drying at 80 C, to obtain white solid that is risedronic acid, the based on amount calculation of 3- Pyridine carbonyl chloride hydrochloride , the yield of risedronic acid was 60%.

According to the analysis of related databases, 6419-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Luohe Medical College; Ding Sujun; He Xinlei; Zhou Haiyang; Zhang Huifen; Li Pinai; (11 pag.)CN104628770; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 57266-69-0, Adding some certain compound to certain chemical reactions, such as: 57266-69-0, name is 3-Chloropicolinic acid,molecular formula is C6H4ClNO2, 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 57266-69-0.

Production example 21 (3) A mixture of 4-iodo-N1-methyl-benzene-1,2-diamine 850 mg, 3-chloro-pyridine-2-carboxylic acid 590 mg, EDC hydrochloride 790 mg, HOBt 46 mg, and pyridine 10 mL at 100C for 12 hr was stirred. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The resultant residue was treated with silica gel column chromatography to give 2-(3-chloro-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazole (hereinafter referred to as Intermediate compound (M6-21)) 930 mg.

According to the analysis of related databases, 57266-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; SHIMIZU, Chie; KAMEZAKI, Masashi; NOKURA, Yoshihiko; EP2952097; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1159827-76-5, 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. 1159827-76-5, name is 7-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5FN2O2, 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.

7-Fluoroimidazo[l,2-a]pyridine-3-carboxylic acid (0.081 g, 0.449 mmol) was dissolved in thionyl chloride (2 mL). To this was added a few drops of DMF and the mixture stirred at ambient temperature for 1 hour. The mixture was concentrated under reduced pressure and the resulting solid was dissolved in 3 mL of 1 :2 DCM:DMF. To this was added 3 -methyl- l-((6-methylpyridin-2-yl)methyl)-lH-indazol-4-amine (0.114 g, 0.451 mmol) followed by diisopropylethylamine (235 mu, 1.35 mmol). This mixture was stirred at ambient temperature for 2 hours, then diluted with water (22 mL), forming a beige precipitate with stirring for several hours. The solids were collected to give 0.100 g (54%) of the title compound. MS (APCI), positive scan, m/z = 415.2 (M+H).

According to the analysis of related databases, 1159827-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; DELISLE, Robert Kirk; HICKEN, Erik James; KENNEDY, April L.; MARESKA, David A.; MARMSATER, Fredrik P.; MUNSON, Mark C.; NEWHOUSE, Brad; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2012/82689; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5345-47-1, 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 5345-47-1, name is 2-Aminonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Containing 13.8 g of 2-amino acid (0.1 mmol) of potassium carbonate and 27.6 g (0.2 mole, 2.0 eq.) Of dimethyl sulfoxide was heated to reflux, then the solution was cooled to ambient temperature, was added 14.2 g of iodine methane (0.1 mole, 1.0 eq) to the mixture, and the solution was stirred for 18 hours, the mixture was filtered and concentrated to give a residual material containing 0.1% aqueous ammonia (5/95 ethanol / dichloromethane) was eluted as after filtration of the liquid silicone pad and the resulting solution was concentrated, the residue was suspended in ether, filtered and dried to give 2-amino-nicotinic acid methyl ester (10.8 g, 71% yield). Analysis of results:

According to the analysis of related databases, 5345-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; ARNDT, JOSEPH; CHAN, TIMOTHY; GUCKIAN, KEVIN; KUMARAVEL, GNANASAMBANDAM; LEE, WEN-CHERNG; LIN, EDWARD YIN-SHIANG; SCOTT, DANIEL; SUN, LIHONG; THOMAS, JERMAINE; VAN VLOTEN, KURT; WANG, DEPING; ZHANG, LEI; ERLANSON, DANIEL; (469 pag.)TWI525093; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem