Tag: M.W:200-300

Reference of 552331-00-7, 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. 552331-00-7, name is 4-Iodopyridin-2-amine. A new synthetic method of this compound is introduced below.

Reference Example 42; 3-(2-aminopyridin-4-yl)-5-phenyl-1,3-oxazolidin-2-oneTo a solution of 4-iodopyridin-2-amine (2.0 g, 9.09 mmol), 5-phenyl-1,3-oxazolidin-2-one (1.7 g, 10.5 mmol) obtained in Reference Example 41 and potassium carbonate (2.5 g, 18.2 mmol) in 1,4-dioxane (30 mL) were added copper iodide (173 mg, 909 mumol) and N,N’-dimethylethylenediamine (80 mg, 909 mumol) at room temperature, and the mixture was heated under reflux for 16 hr under an argon stream. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.78 g, yield 77%) as crystals.melting point 155-156 C. (ethyl acetate-hexane)1H-NMR (CDCl3) delta: 3.90 (1H, dd, J=9.0, 7.5 Hz), 4.35 (1H, t, J=9.0 Hz), 4.49 (2H, br s), 5.64 (1H, t, J=7.5 Hz), 6.67 (1H, dd, J=6.0, 2.1 Hz), 6.93 (1H, d, J=2.1 Hz), 7.34-7.50 (5H, m), 8.00 (1H, d, J=6.0 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,552331-00-7, 4-Iodopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2011/39893; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 33252-64-1, 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. 33252-64-1, name is 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

3-Nitro-5-(trifluoromethyl)pyridin-2-ol (31.00 g, 149 mmol) was dissolved in acetonitrile (250 ml) to give a dark brown solution. Phosphorus(V) oxybromide (85 g, 298 mmol) was added and the mixture was heated at reflux for 4 hours and then stirred at RT overnight. The reaction mixture was quenched by pouring into vigorously stirring water (600 ml) containing sodium hydrogencarbonate (1 10 g). The dark brown mixture was extracted with DCM (3 x 200 ml) and the organic phase was washed with water (200 ml) and brine (100ml), dried (MgS04) and concentrated under reduced pressure to afford the title product as a brown oil. H-NMR: [400MHz, CDCI3, ? 8.87 (1 H, d, J = 1.4Hz, ArH), 8.39 (1 H, d, J = 1 .9Hz, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-64-1, 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren Mark; WO2013/38373; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 61338-13-4, 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 61338-13-4, name is 2-(4-Methyl-2-phenylpiperazin-1-yl)nicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Stirring blade,In a 1 L three-necked flask equipped with a thermometer, 60 g (201.8 mmol) of the pyridine carboxylic acid compound was suspended in 270 mL of tetrahydrofuran,It was cooled to 10 C.Under nitrogen flow70% sodium bis (2-methoxyethoxy) aluminum hydrideOf a toluene solution240 g (706.2 mmol) was added dropwise,The reaction was carried out at 40 C. for 5 hours.After completion of the reaction,The reaction solution was cooled to 10 C.,The reaction solution was added to 275 mL of a 35% by mass Rochelle salt aqueous solution cooled to 10 C. with stirring for 5 minutes.The temperature of the mixed solution at this time was 15 C.In addition, precipitation of aluminum hydroxide was not confirmed.Thereafter, the mixture was stirred for 10 minutes, and an organic layer and an aqueous layer were separated.The organic layer was concentrated under reduced pressure to obtain a pyridine methanol compound as a residue.240 mL of diethyl ether was added to the residue, and the mixture was stirred at room temperature for 30 minutes to obtain a crystallized pyridine methanol compound.After filtering the crystals,Dried under reduced pressure at 40 C. for 5 hours,Pyridine methanol compound (51 g).(Yield 89%, purity 99.3%, excess reductant amount 0.2%).

According to the analysis of related databases, 61338-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOKUYAMA CORPORATION; KASAI, SOKO; MIYAOKU, TAKAYUKI; (10 pag.)JP2017/154976; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588729-99-1, Adding some certain compound to certain chemical reactions, such as: 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine,molecular formula is C5H4BrClN2, 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 588729-99-1.

a) (5-Bromo-2-chloro-pyridin-3-yl)-methyl-amine A solution of 5-bromo-2-chloro-pyridin-3-ylamine (CAS registry 588729-99-1) (565 mg, 2.72 mmol) in THF (4 ml) at 0 C. was treated with BuLi 1.6M in hexane (0.17 ml, 0.17 mmol), the resulting mixture was stirred at 0 C. for 0.5 h, then methyl iodide (0.17 ml, 2.72 mmol) was slowly added. The reaction mixture was allowed to warm to rt and was stirred for 18 h. The orange/brown mixture was poured into sat. aq. NaHCO3 soln., and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated and purified by flash chromatography on silica gel (cyclohexane/EtOAc 95:5 to 60:40) to afford the title compound as an orange solid (354 mg, 59% yield). HPLC RtM1=0.94 min; ESIMS: 221, 223, 225 [(M+H)+]. 1H NMR (400 MHz, DMSO-d6): delta 7.65 (d, 1H), 7.14 (d, 1H), 6.11 (d, 1H), 2.74 (d, 3H).

According to the analysis of related databases, 588729-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); 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. 1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Synthesis of methyl 6-bromo-5-fluoropicolinate To a solution of 6-bromo-5-fluoropicolinic acid (1.0 equiv.) in methanol (0.2 M) was added H2SO4 (4.2 equiv.) and the reaction was stirred at room temperature for two hours. Upon completion of the reaction as monitored by LC/MS, the reaction was diluted with ethyl acetate and quenched slowly with saturated aqueous NaHC03. The reaction was poured into a separatory funnel and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate, filtered, and concentrated in vacuo to provide methyl 6-bromo-5-fiuoropicolinate as a white solid (>99%). LC/MS = 233.9/235.9 (M+H), Rt = 0.69 min.

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, 1052714-46-1, 6-Bromo-5-fluoropicolinic acid.

Reference:
Patent; NOVARTIS AG; BURGER, Matthew; DRUMM III, Joseph; NISHIGUCHI, Gisele; RICO, Alice; SIMMONS, Robert Lowell; TAFT, Benjamin; TANNER, Huw; WO2013/175388; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1211540-92-9, Adding some certain compound to certain chemical reactions, such as: 1211540-92-9, name is 3-Bromo-4-chloro-5-fluoropyridine,molecular formula is C5H2BrClFN, 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 1211540-92-9.

Preparation 9: (l-(3-amino-5-fluoropyridin-4-yl)piperidin-4-yl)(4-methylpiperazin-l- yl)methanone (hydrochloride) 17 Scheme 4 Step 1: 3-bromo-4-chloro-5-fluoropyridine hydrochloride 18 [00264] To a solution of diisopropylamine (6.899 g, 9.555 mL, 68.18 mmol) in THF (75 mL) cooled to -78C, was added butyllithium (25 mL of 2.5 M in hexanes, 62.5 mmol). The reaction mixture was allowed to warm to -20C then cooled back down to -78C. A solution of 3-bromo-5-fluoro-pyridine (10 g, 56.82 mmol) in THF (25 mL) was added dropwise keeping temperature below -70C (approx 30 mins). The reaction mixture was stirred at – 78C for 30 min and a solution of 1, 1, 1,2,2,2-hexachloroethane (14.8 g, 62.5 mmol) in THF (20 mL) was then added dropwise, keeping temperature below -70C (over approx 30 mins). The mixture was stirred at -78C for 20 minutes, allowed to warm to room temperature, cooled back to 0C and quenched with water (100 mL). EtOAc (400 mL) was then added, and organic layer separated, washed with water (2x), brine (lx), dried (MgS04), filtered and concentrated in vacuo to leave a brown solid. The solid was triturated in pentane (lOOmL) for 10 minutes, then filtered. The filtrate was concentrated in vacuo to afford product as a brown 011 that turned to a crystalline solid on standing, 11.85 g, 89%). 1H NMR (DMSO-d6) delta 8.78 (s, 1H), 8.76 (s, 1H). [00265] To a solution of 3-bromo-4-chloro-5-fluoro-pyridine (7.56 g, 32.18 mmol) in pentane (100 mL) was added hydrogen chloride (2M in ether) (17.7 mL of 2 M, 35.4 mmol). An off-white precipitate formed instantly. The mixture was stirred for 5 minutes then the solid was collected by filtration, washed with pentane and dried by suction to afford the desired product as an off-white solid (4.79 g, 60%). 1H NMR (DMSO-d6) delta 8.77 (s, 1H), 8.75 (s, 1H).

According to the analysis of related databases, 1211540-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DAVID, Chris; DURRANT, Steven; FRAYSSE, Damien; JIMENEZ, Juan-Miguel; KAY, Dave; KNEGTEL, Ronald; O’DONNELL, Michael; PIERARD, Francoise; PINDER, Joanne; STORCK, Pierre-Henri; TWIN, Heather; WO2014/143242; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 884495-39-0, 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. 884495-39-0, name is 5-Bromo-2-methoxypyridin-3-amine, molecular formula is C6H7BrN2O, 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.

A mixture of 1.80 g (8.8 mmol) C-5, 2.29 mL (17 mmol) 2,4-difluorobenzenesulphonyl chloride, 1.07 mL (13.3 mmol) pyridine and 20 mL DCM is stirred at RT over night.100 mL DCM is added and the reaction mixture is extracted three times with 50 mL aqueous 1M HCl. The organic layer is dried over MgS04 and the solvent is removed under reduced pressure. The solid is dissolved in water/MeCN and further purified by RP- chromatograpy. Yield: 2,9 g (86%).

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 884495-39-0, 5-Bromo-2-methoxypyridin-3-amine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WUNBERG, Tobias; VEEN, VAN DER, Lars; KRAEMER, Oliver; WO2012/101184; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 951626-91-8, 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine, 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, Recommanded Product: 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine, blongs to pyridine-derivatives compound. Recommanded Product: 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine

5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine (235 mg) was dissolved in dichloromethane (5 ml). Di-tert-butyl dicarbonate (248 mg) and N,N-dimethylaminopyridine (1.2 mg) were added and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (297 mg).MS (ESI) m/z: 331 (M+H)+.1H-NMR (CDCl3) delta: 1.67 (9H, s), 7.65 (1H, s), 8.05 (1H, d, J=2.2 Hz), 8.58 (1H, d, J=2.2 Hz).

The synthetic route of 951626-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; US2011/82138; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-78-7, 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. 153034-78-7, name is 2-Fluoro-3-iodo-5-methylpyridine. A new synthetic method of this compound is introduced below.

(2) Synthesis of 2-fluoro-4-iodo-3,5-dimethylpyridine Diisopropylamine (88 mL) was added to THF (1.2 L), and the mixture was cooled to -18 C. in a nitrogen atmosphere. A 2.69 M solution of n-butyllithium in hexane (215 mL) was added dropwise to the solution. After completion of the dropwise addition, the mixture was warmed to -5 C. with stirring over 30 minutes. The reaction mixture was cooled to -72 C. A solution of 2-fluoro-3-iodo-5-methylpyridine (109.69 g) in TIE (240 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -74 C. for 1.5 hours. A solution of methyl iodide (36 mL) in THF (160 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -70 C. to -74 C. for two hours. After completion of the reaction, water (200 mL) was added to the reaction mixture at the same temperature. The mixture was stirred at the same temperature for two minutes. The reaction mixture was returned to room temperature, and water (1.2 L) was then added. The mixed solution was stirred for three minutes. Water (300 mL) was further added. The mixture was extracted with MTBE (1.2 L). The organic layer was washed with brine (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. n-heptane (100 mL) was added to the residue, followed by cooling. The precipitated solid was collected by filtration. The residue was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. This operation was repeated twice to give the title compound (86.9 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.39-2.40 (m, 6H), 7.80-7.82 (m, 1H). ESI-MS m/z 252 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-78-7, 2-Fluoro-3-iodo-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52833-94-0, 2-Amino-5-bromonicotinic acid, 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, 52833-94-0, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5BrN2O2

A mixture of 2-amino-5-bromonicotinic acid (2.0 g, 9.20 mmol), HOBT (1.40 g, 11.2 mmol), EDCI (3.52 g, 18.4 mmol), Et3N (4.68 g, 46.0 mmol) and NH4C1 (2.48 g, 46.0 mmol) in DMF (100 mL) was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, suspended in water and extracted with CH2C12. The organic layer was washed with brine, dried over Na2S04 and concentrated to give the product of 2-amino-5- bromonicotinamide (1.80 g, yield: 80%), which was used for the next step without further purification. NMR (DMSO-i, 400 MHz) delta 8.14 (dd, J= 4.4 Hz, 2.4 Hz, 2H), 8.04 (s, 1H), 7.46 (s, 1H), 7.37 (s, 2H). MS (M+H)+: 216 / 218.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52833-94-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem