Tag: M.W:200-300

Application of 49669-13-8, Adding some certain compound to certain chemical reactions, such as: 49669-13-8, name is 2-Acetyl-6-bromopyridine,molecular formula is C7H6BrNO, 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 49669-13-8.

A solution of l-(6-bromopyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 mL) at 0C was treated with methyl magnesium bromide (8.33 mL, 25.0 mmol). After 3 hours, water was added to quench the excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound.Calc’d for C8HnBrNO [M+H]+: 216, Found: 216.

According to the analysis of related databases, 49669-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/156726; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 86847-84-9 ,Some common heterocyclic compound, 86847-84-9, molecular formula is C10H13ClN2O, 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 iert-BuLi (1.7 M in pentane) was slowly added over half hour to a solution of compound 13-2 (1.25 g, 5.91 mmol) in anhydrous THF at -78 C. After the reaction was stirred for 3 h at -78 C, a solution of iodine (1.8 g, 7.09 mmol, 1.2 equiv.) in THF was added and the reaction mixture was allowed to warm up to room temperature and stirred for 14 h. The reaction was concentrated and the residue diluted with methylene chloride. The organic layer was washed sequentially with 10% aqueousNa2S203 and NaHC03 and concentrated under reduced pressure. The product was purified by flash chromatography using Combiflash and employing a gradient of 0-20% EtOAc in Hexanes to afford 1.50 g (4.45 mmol, 73% yield) of 13-3.

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. 86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 718608-10-7 , The common heterocyclic compound, 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, 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 8-chloro-3-((1S,2S)-2-hydroxycyclohexyl)-6-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)quinazolin-4(3H)-one (130 mg, 0.321 mmol), cesium carbonate (314 mg, 0.964 mmol) and 5-(bromomethyl)-2-methylpyridine hydrobromide (103 mg, 0.385 mmol) in THF (5.0 ml) was sparged under nitrogen for 5 minutes. The mixture was treated with [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (26.2 mg, 0.032 mmol), sparged under nitrogen (3 minutes) and then heated at 60 C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (25 mL) and water (25 mL), and extracted with ethyl acetate (3 x 25 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (90:10 to 0:100; water containing 0.1% formic acid : acetonitrile containing 0.1% formic acid) to yield the title compound. 1H NMR (400MHz, CD3OD): delta 8.35 (d, J = 2.0 Hz, 2H), 8.02 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 7.62 (d, J = 8.0, 2.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 4.51- 4.49 (m, 1H), 4.13 (s, 2H), 4.07- 4.02 (m, 1H), 2.51 (s, 3H), 2.20- 2.10 (m, 1H), 1.97- 1.84 (m, 4H), 1.48- 1.46 (m, 3H) ppm. LRMS C21H23ClN3O2: calc?d 384.1, obs 384.2 (M+H) +.

The synthetic route of 718608-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; MOHANTY, Subhendu Kumar; LATTHE, Prashant R.; KUDUK, Scott D.; HOYT, Scott B.; (107 pag.)WO2017/155816; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22282-70-8, 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.22282-70-8, name is 2-Fluoro-4-iodopyridine, molecular formula is C5H3FIN, molecular weight is 222.99, as common compound, the synthetic route is as follows.

Example 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H).

The chemical industry reduces the impact on the environment during synthesis 22282-70-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7477-10-3 ,Some common heterocyclic compound, 7477-10-3, molecular formula is C6H3ClN2O4, 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.

Methyl 6-chloro-5-nitronicotinate was purchased from Sigma Aldrich or synthesized as follows. Toa solution of 6-chloro-5-nitronicotinic acid (Ark Pharm, Inc., 2.5 g, 12.3 mmol) in dry DMF (30mL) were added K2CO3 (2.5 g, 18.5 mmol) and iodomethane (8.76 g, 61.7 mmol). The solution wasstirred at room temperature for 24 h, then poured onto ice, and extracted with EtOAc (100 mL × 3).The organic layer was washed with H2O (100 mL × 2) and brine (100 mL), and dried over MgSO4.The solvent was evaporated under reduced pressure and the residue was purified by flash columnchromatography (EtOAc/n-hexane = 1/2) to afford 10 (2.4 g, 92percent) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7477-10-3, its application will become more common.

Reference:
Article; Takamura, Yuta; Takahashi, Manami; Nishii, Midori; Shibahara, Osamu; Watanabe, Masaki; Fujihara, Michiko; Kakuta, Hiroki; Bioorganic and Medicinal Chemistry Letters; vol. 29; 15; (2019); p. 1891 – 1894;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 934279-60-4 ,Some common heterocyclic compound, 934279-60-4, molecular formula is C7H3ClF3NO, 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 crude 2-chloro-5-trifluoromethylpyridine-3-carbardehyde in ethanol (60 ml_), sodium tetraborohydride (2.90 g, 0.077 mol) is added portionwise and stirred for 30 min at room temperature. After adding sat. ammonium chloride solution, the mixture is extracted with ethyl acetate. The organic layer is washed with sat. ammonium chloride solution, brine, dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel column chromatography to give 2-chloro-5-trifluoromethylpyridin-3-ylmethanol.

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. 934279-60-4, 2-Chloro-5-(trifluoromethyl)nicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; WO2008/58967; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 914358-72-8, 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. 914358-72-8, name is 5-Bromo-3-chloro-2-methylpyridine, molecular formula is C6H5BrClN, 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.

Intermediate 443-Chloro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine; A suspension of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (0.836 g, 3.29 mmol), 5-bromo-3-chloro-2-methylpyridine (Intermediate 43, 0.34 g, 1.65 mmol), and potassium acetate (0.485 g, 4.94 mmol) in dioxane (5 mL) was degassed with a stream of N2 (g) for a couple of min. PdCl2(dppf) CH2Cl2 (0.067 g, 0.08 mmol) was added and the mixture was heated at reflux under N2 (g) for 1.5 h. The mixture was allowed to cool to r.t. and was then filtered. The filter cake was washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography (40 g SiO2, gradient elution with 0-80% EtOAc in heptane to yield the title compound (0.44 g, quantitative yield): 1H NMR (500 MHz, CDCl3) delta ppm 1.35 (s, 12H), 2.65 (s, 3H), 7.95-8.03 (m, 1H), 8.69 (d, 1H); MS (ES+) m/z 172 [M+H]+(mass corresponding to the boronic acid).

According to the analysis of related databases, 914358-72-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2012/165347; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 878197-68-3, Adding some certain compound to certain chemical reactions, such as: 878197-68-3, name is 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde,molecular formula is C8H5BrN2O, 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 878197-68-3.

To a solution of X4-019-5a (1.7 g, 16.7 mmol) and THF (10 ml) was added nBuLi (5.6 ml, 14.1 mmol, 2.5 M in hexanes) dropwise at -20 C. After stirred at -20 C for 20 mm, the mixture was added slurry of X4-019-5 (1.5 g, 6.7 mmol) in THF (30 ml) dropwise at -20C and stirred at -10 C for 7 hours. After quenched with sat NH4C1 aq. (pH = 8), the mixture was extracted with DCM/i-PrOH (10/1). The organic layer was washed with sat NaHCO3 aq., dried over Na2504, filtered and concentrated in vacuum. The residue was purified by column chromatography to give product X4-019-6 (785 mg, 48%) as yellow oil. LC-MS (Agilent LCMS 1200-6120, Column: Waters X-Bridge C18 (50mm *4.6 mm*3.5 jim); Column Temperature: 40C; Flow Rate: 2.0 mL/min; Mobile Phase: from 95% [water + 10 mM NH4HCO3] and 5% [CH3CN] to 0% [water + 10 mM NH4HCO3] and 100% [CH3CN] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95% [water + 10 mM NH4HCO3] and 5% [CH3CN] in 0.1 mm and under this condition for 0.7 mm). Purity: 94.5%, Rt = 1.31 mm; MS Calcd.: 224.13; MS Found: 245.1 [M+H]t

According to the analysis of related databases, 878197-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; X4 PHARMACEUTICALS, INC.; BOURQUE, Elyse Marie Josee; SKERLJ, Renato; (239 pag.)WO2017/223239; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 639091-75-1, 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 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A slurry of methyl 2-((tert-butoxycarbonyl)amino)isonicotinate (50.4 g, 200 mmol) in DMF (500 mL) was cooled to 0C and sodium hydride (10.4 g, 60% in mineral oil, 260 mmol) was added portion wise. The mixture was allowed to warm to RT and stirred for 30 min. To the reaction iodomethane (37.2 g, 262 mmol) was slowly added. The resulting mixture was stirred at RT overnight. The reaction was quenched by addition of aqueous ammonium chloride (100 mL) and diluted with water (400 mL). The mixture was extracted with EA (250 mL x 2). The combined organic phase was washed with water (100 mL) and brine (100 mL), dried over MgSO4 and concentrated. The residue was chromatographed, eluting with 5:1 hexane:EA) to give the product as colorless oil (48.9 g, 92%).1H NMR (400 MHz, CDCl3) delta 1.54 (s, 9H), 3.42 (s, 3H), 3.94 (s, 3H), 7.52 (d, 1H), 8.27 (s, 1H), 8.48 (d, 1H).

According to the analysis of related databases, 639091-75-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXITHERA PHARMACEUTICALS, INC.; CHENARD, Bertrand, L.; XU, Yuelian; STASSEN, Frans, L.; HAYWARD, Neil, J.; (225 pag.)WO2018/118705; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 194673-12-6, 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 194673-12-6 as follows.

A solution of 6-hydroxy-2-trifluoromethyl-4,5-dihydro-pyridine-3-carboxylic acid ethyl ester (Description 16) (4.7 g, 19.8 mmol, 1 eq) and N-bromosuccinimide (3.51 g, 19.8 mmol, 1 eq) in 15 ml of carbon tetrachloride was heated under reflux for 20 h. The resulting precipitate was filtered off and the filtrate was concentrated under reduced pressure to afford a brownish solid that was purified by flash chromatography (silica gel, eluent gradient: from hexane/ethyl acetate 9:1 to hexane/ethyl acetate 8:2). The title compound was obtained as a white solid (4.3 g, yield = 92%). LC-MS (ESI+), MH+: 236

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,194673-12-6, its application will become more common.

Reference:
Patent; Glaxo Group Limited, Glaxo Group Limited; WO2004/29027; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem