Tag: M.W:200-300

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 67625-36-9, name is Ethyl 5-chloroimidazo[1,2-a]pyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. name: Ethyl 5-chloroimidazo[1,2-a]pyridine-2-carboxylate

A mixture of the compound (1.28 g) obtained in (1), 4-chlorophenylboronic acid (1.78 g), tris(dibenzylidenacetone)dipalladium (0) chloroform adduct (0.34 g), 1,3-bis(2,6-diisopropylphenyl) imidazolium chloride (0.5 g), cesium carbonate (11.2 g) and dioxane (50 mL) was stirred for 24 hours at 80C. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue, which was then Celite filtered. Water was added to the filtrate, which was then extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography and recrystallized from diisopropyl ether to obtain ethyl 5-(4-chlorophenyl)imidazo[1,2-a]pyridine-2-carboxylate (830 mg) as colorless crystals. 1H-NMR (CDCl3, 400MHz); delta 1.42 (3H, t, J=7.2Hz), 4.44 (2H, q, J=7.2Hz), 6.81 (1H, d, J=6.8Hz), 7.34 (1H, m), 7.56 (4H, m), 7.70 (1H, d, J=9.2Hz), 8.18 (1H, s)

With the rapid development of chemical substances, we look forward to future research findings about 67625-36-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1849465; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 886365-47-5, 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 886365-47-5, name is 1-(5-Bromo-2-chloropyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-(5-bromo-2-chloropyridin-3- yl)ethanone (4.85 g, 0.85 mmol) and N,N-dimethylformamide dimethyl acetal (15 mL, 113 mmol) was stirred at 85C for 90 minutes in an oil bath. The mixture was cooled to room temperature, and concentrated under reduce pressure. The residue was diluted by addition of ethanol (30 mL) and water (15 mL), acetic acid (3.3 mL, 58 mmol) and 2-hydrazinoethanol (1.83 mL, 26.9 mmol) was added thereto at room temperature, and the mixture was stirred at 90C for 4 hours in an oil bath. The mixture was cooled to room temperature, and neutralized by addition of a 1.0 mol/L aqueous solution of sodium hydroxide, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified in an automatic chromatography apparatus (n-hexane/ethyl acetate = 100/0- 0/100) to obtain 2-[5-(5-bromo-2-chloropyridin-3-yl)- 1H-pyrazol-1-yl]ethanol (3.62 g) as a mixture containing positional isomers. To a solution of 2-[5-(5-bromo-2- chloropyridin-3-yl)-1H-pyrazol-1-yl]ethanol (3.62 g) as a mixture containing positional isomers obtained in the above step in N,N-dimethylformamide (240 mL) was added potassium carbonate (3.31 g, 23.9 mmol) at room temperature, and the mixture was stirred at 120C for 2 hours in an oil bath. The reaction mixture was cooled, and an insoluble material was filtered off. The residue was washed with ethyl acetate, and the filtrate and the washes were combined. The solvent was distilled off under reduced pressure, and the residue was purified in an automatic chromatography apparatus (Yamazen Co. Ltd., High-flashTM column Amino, n-hexane/ethyl acetate = 100/0- 30/70) to obtain the title compound (101 mg, yield for 2 steps: 57%)?H NNR spectrum (CDC13, 400MHz) oe: 8.27 (1H, d, J =2.3 Hz), 8.18 (1H, d, J= 2.3 Hz), 7.55 (1H, d, J=2.0 Hz), 6.69 (1H, d, J = 2.0 Hz), 4.74-4.72 (2H, m),4.62-4.60 (2H, m)

According to the analysis of related databases, 886365-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; MIYAZAKI, Shojiro; INUI, Masaharu; KUROSAKI, Yasunobu; YAMAMOTO, Yuko; IZUMI, Masanori; SOMA, Kaori; PINKERTON, Anthony; KISHIDA, Masamichi; (309 pag.)WO2018/119444; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 107351-82-6 , The common heterocyclic compound, 107351-82-6, name is 2-Bromo-5-phenylpyridine, molecular formula is C11H8BrN, 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 5 Synthesis of 2,4-bis(4-tert-butylphenyl)-6-[4-(5-phenylpyridin-2-yl)phenyl]-1,3,5-triazine Under a stream of argon, 3.5 ml of a pentane solution containing 5.2 mmol of tert-butyl lithium was slowly added to 15 ml of tetrahydrofuran cooled to -78C, and 10 ml of tetrahydrofuran in which 0.61 g of 2-bromo-5-phenylpyridine had been dissolved was further added dropwise to this solution. After stirring at -78C for 30 minutes, 1.64 g of dichloro(tetramethylethylenediamine)zinc(II) was added thereto and stirred at -78C for 10 minutes and then at room temperature for 2 hours. A 35 ml portion of tetrahydrofuran prepared by dissolving 1.00 g of 2-(4-bromophenyl)-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine synthesised by the method of Reference Example 1 and 0.12 g of tetrakis(triphenylphosphine)palladium(0) therein was added to this solution and stirred under heating reflux for 10 hours. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was recrystallized from dichloromethane-methanol. The thus obtained crude product was purified by a silica gel column chromatography (eluding solution hexane:dichloromethane = 3:2 to 4:3) and then again recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2,4-bis(4-tert-butylphenyl)-6-[4-(5-phenylpyridin-2-yl)phenyl]-1,3,5-triazine (1.05 g, yield 91%). Its melting point is shown in Table 4. In this case, a distinct point of glass transition was not observed. 1H-NMR (CDCl3): delta 1.45 (s, 18H), 7.44-7.60 (m, 3H), 7.65 (d, J=8.6 Hz, 4H), 7.88 (d, J=8,5 Hz, 2H), 7.88-7.94 (m, 1H), 8.07-8.15 (m, 3H), 8.74 (d, J=8.6 Hz, 4H), 8.93 (d, J=8.5 Hz, 2H), 9.09 (d, J=1.7 Hz, 1H). 13C-NMR (CDCl3): delta 31.2, 35.1, 120.3, 125.6, 126.9, 127.0, 128.8, 129.1, 129.6, 133.6, 134.1, 135.1, 136.2, 138.8, 141.2, 148.1, 156.1, 156.6, 170.9, 171.5.

The synthetic route of 107351-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH CENTER; EP1930329; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60010-03-9, 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 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 2,6-dichloro-4-methyl-3-nitropyridine (300 mg, 1.449 mmol) and sodium bicarbonate (243 mg, 2.90 mmol) in Tetrahydrofuran (THF) (20 mL)) was added (S)-dimethyl 2-aminosuccinate hydrochloride (430 mg, 2.174 mmol) at 0 C. under nitrogen. Then the reaction mixture was stirred at 65 C. for 24 hr. The reaction was monitored by TLC. The reaction mass filtered and washed with EtOAc (2×30 mL). The filtrate was concentrated under reduced pressure to give the crude material. The crude product was added to a neutral alumina column and was eluted with Hex/EtOAc (9:1). Collected fractions were concentrated under reduced pressure to afford the desired product (250 mg, 0.742 mmol, 51.2% yield) as yellow gummy liquid, LCMS (m/z) 339.1 (M+H)+.

According to the analysis of related databases, 60010-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); 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.103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, molecular formula is C7H6BrNO2, molecular weight is 216.032, as common compound, the synthetic route is as follows.Safety of 5-Bromo-2-methoxynicotinaldehyde

(5-bromo-2-methoxypyridin-3-yl)methanol 5-Bromo-2-methoxynicotinaldehyde (2 g, 9.26 mmol) was suspended in methanol (40 mL) and cooled to 0 C. Sodium borohydride (0.350 g, 9.26 mmol) was added, causing bubbling. The reaction mixture was stirred at 0 C. for 15 minutes, the flask was removed from the ice bath, and the mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was concentrated, and the crude material was taken up in methyl tert-butyl ether and saturated aqueous sodium bicarbonate. The phases were separated, and the organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound (1.876 g, 8.60 mmol, 93% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.15 (d, J=2.5 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 4.66 (d, J=6.2 Hz, 2H), 3.99 (s, 3H), 2.15 (t, J=6.3 Hz, 1H); MS (DCI+) m/z 217.8 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (247 pag.)US2018/99932; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, 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, Formula: C5H3Cl2N3O2, blongs to pyridine-derivatives compound. Formula: C5H3Cl2N3O2

Step B. 2,6-Dichloro-pyridine-3,4-diamineTo a solution of 2,6-dichloro-3-nitro-pyridin-4-amine (2.6 g, 14.4 mmol) from Step A in MeOH (150 mL) was added Raney Nickel catalyst (2 g) and the reaction agitated under a hydrogen atmosphere in a Parr apparatus (35 p.s.i.) for 2 h . The reaction mixture was filtered through a pad of Celite and concentrated to yield the title compound. MS: m/z – 178 (M + 1).

The synthetic route of 2897-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/153852; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1042141-37-6, 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.1042141-37-6, name is Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate, molecular formula is C9H7BrN2O2, molecular weight is 255.07, as common compound, the synthetic route is as follows.

A mixture of methyl S-bromo-lJ-diazabicyclo^.S.Ojnona^^ojS-tetraene-S-carboxylate (0.65 mmol, 165 mg), tert-but5d N-methyl-N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2-yl]carbamate (0.98 mmol, 312 mg), Pd(dprhof)Cl2*DCM (65 mumol, 53mg) and cesium carbonate (1.95 mmol, 656 mg) in DMF (5 mL) was heated at 80 CC under an argon atmosphere for 1 h. The reaction mixture was filtered and the solvent was evaporated in vacuo. The residue was purified by silica gel chromatography (EtOAc / hep) to give 150 mg of methyl 2-[6-[methyl-[(2-methylpropan- 2-yl)oxycarbonyl]amino]pyridin-3-yl]imidazo[2,l-fJpyridine-6-carboxylate as a yellow solid. MS m/z (M+H) 383

The chemical industry reduces the impact on the environment during synthesis 1042141-37-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2008/91195; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 29241-60-9, name is 5-Bromo-2-chloro-3-methylpyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5BrClN

To a solution of 5-bromo-2-chloro-3-methylpyridine (300 g, 1.45 mol) in MeOH (3 L) was added freshly prepared sodium methoxide (156 g, 2.9 mol), and the reaction mixture was heated to reflux and stirred overnight. The reaction mixture was quenched with acetic acid (600 mL) and concentrated under reduced pressure. The crude mixture was diluted with ethyl acetate (3 L) and washed with water (3 L). The aqueous layer was extracted with ethyl acetate (3 L) and the combined organic layers were washed with brine (3 L), dried over anhydrous MgSCL and evaporated under reduced pressure to provide crude 5-bromo-2-methoxy-3-methylpyridine (220 g, 75%). l NMR (300 MHz, CDCl3) d (s, 1 H), 7.47 (s, 1 H), 3.93 (s, 3 H), 2.05 (s, 3 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, 29241-60-9, 5-Bromo-2-chloro-3-methylpyridine.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CUNNINGHAM, Christian; BEROZA, Paul Powell; CRAWFORD, James John; LEE, Wendy; RENE, Olivier; ZBIEG, Jason Robert; LIAO, Jiangpeng; WANG, Tao; YU, Chen; (208 pag.)WO2020/51099; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 179687-79-7, Adding some certain compound to certain chemical reactions, such as: 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine,molecular formula is C12H9ClN2O3, 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 179687-79-7.

2-(2-CHLORO-4-NITRO-PHENOXYMETHYL)-PYRIDINE (2.4 g, 9.07 mmol) is suspended in MeOH (30 ML) and treated wet 5% Pt/C (Degussa type, ALDRICH, 0. 8 g). The flask is flushed with hydrogen gas from a balloon and the reaction mixture is stirred under hydrogen atmosphere until reaction is complete by TLC (ca 2 hours). The reaction mixture is filtered through a Celite plug and the solvent is removed under reduced pressure. The crude product is redissolved in DCM, dried (MGS04) and concentrated to yield 1.7 g (7.23 mmol, 80%) of the desired product.

According to the analysis of related databases, 179687-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA, INC.; WO2004/46101; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60154-05-4, 5-Iodo-1-methylpyridin-2(1H)-one, 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, HPLC of Formula: C6H6INO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H6INO

General procedure: A mixture of potassium fluoride (0.15g, 2.6mmol) and copper iodide (I) (0.50g, 2.6mmol) was heated under reduced pressure until a greenish color appeared, and after cooling to rt, an iodo compound (1.0mmol) in DMF/HMPA (2.5mL each) and trimethyl(trifluoromethyl)silane (0.38mL, 2.6mmol) were added to this flask successively. The mixture was stirred for the specified time and at the indicated temperature (see Table 2). After quenching with satd aqueous ammonium chloride, usual workup and purification by silica gel chromatography yielded the trifluoromethylated product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60154-05-4, 5-Iodo-1-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Article; Kawasaki-Takasuka, Tomoko; Yamazaki, Takashi; Tetrahedron; vol. 71; 38; (2015); p. 6824 – 6831;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem