Month: March 2022

Application of 65515-39-1, 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.65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, molecular weight is 162.19, as common compound, the synthetic route is as follows.

(a) 4-ethyl-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (3.5 g, 21.58 mmol) in THF (100 mL) was added LHMDS (1M in THF) (22.66 mL, 22.66 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction was stirred at this temperature for 1 h. lodomethane (2.418 mL, 22.66 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride (60 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2x). The combined organics were dried over Na2S04, filtered, concentrated, and purified by flash chromatography (0-5% EtOAc in hexanes, 80 g column; re-columned using 0-5% EtOAc in hexanes, 80 g column) to afford 4-ethyl-2-methoxy-6-methylnicotinonitrile (2.01 g, 90% purity) as a white crystalline solid. LC-MS(ES) m/z = 176.9 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 65515-39-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-79-4, 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. 128071-79-4, name is 4-Bromo-2-fluoro-3-methylpyridine. A new synthetic method of this compound is introduced below.

To a reaction flask containing a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (5.93 g, 20.17 mmol) in Dioxane (120 mL) were added 4-bromo-2-fluoro-3-methylpyridine (3.72 g, 19.58 mmol), Water (40.0 mL) and Na2C03 (8.30 g, 78 mmol). After the mixture was degassed with Ar for 10 min, Pd(Ph3P)4 (1.131 g, 0.979 mmol) was added. The flask was sealed and the mixture was heated to 100 C over night. The reaction mixture was cooled down and diluted with EtOAc and water, plus sonication to break up solids, then transferred to a separation funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2S04, filtered and concentrated in vacuo to afford a white precipitate in a pale gold residue. The extract was purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give (0534) Intermediate 27B (gold pale oil, 5.01 g, 17.72 mmol, 91% yield). LC-MS Anal. Calc’d for C16H20FNO2 277.15, found [M+H] 278.1. Tr = 1.02 min (Method A). NMR (400MHz, chloroform-d) delta 7.94 (d, J=5.0 Hz, 1H), 6.89 (dd, J=5.1, 0.9 Hz, 1H), 5.79 – 5.49 (m, 1H), 4.18 (q, J=7.1 Hz, 2H), 2.55 – 2.28 (m, 4H), 2.26 – 2.11 (m, 5H), 2.00 – 1.86 (m, 2H), 1.55 – 1.41 (m, 1H), 1.29 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-79-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109613-97-0, 2-Bromo-4-methoxypyridin-3-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, Application In Synthesis of 2-Bromo-4-methoxypyridin-3-amine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Bromo-4-methoxypyridin-3-amine

To a solution of 2-bromo-4-methoxy-pyridin-3-ylamine (540 mg, 2.66 mmol) in pyridine (20 mL) at 0 C is added ethyl chloroformate (0.38 mL, 3.99 mmol). After 30 min, more chloro formate is added (~18 mmol) is added until the reaction goes to completion. The mixture is partitioned between sat. NaHC03 and EtOAc. The two layers are separated, and the aqueous layer is extracted with EtOAc once. The combined organic layers are washed with H20 and brine, dried over MgS04, filterd, and concentrated in vacuo. The crude material is purified on silica gel with EtOAc/MeOH (100/0 to 90/10) as eluant to yield 0.54 g of the product as a white crystalline solid. 1H NMR (CDC13, 300 MHz) 8.18 (d, J= 5.6, 1H), 6.84 (d, J= 5.7, 1H), 6.02 (br s, 1H), 4.23 (q, J = 7.0, 2H), 3.92 (s, 3H), 1.31 (t, J= 7.2, 3H). LC Rt: 1.89 min; LCMS m/z 275 (M+l, 100%).

The synthetic route of 109613-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; CHOI-SLEDESKI, Yong Mi; NIEDUZAK, Thaddeus R.; POLI, Gregory B.; SHUM, Patrick Wai-Kwok; STOKLOSA, Gregory T.; ZHAO, Zhicheng; WO2011/78984; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 847729-27-5 ,Some common heterocyclic compound, 847729-27-5, molecular formula is C7H5ClFNO2, 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.

Description 90: methyl 5-fluoro-2-(3-((4-fluoro-2- methylphenyl)amino)azetidin-1-yl)nicotinate (D90)A mixture of methyl 2-chloro-5-fluoronicotinate (D69) (199.85 mg, 1 .054 mmol) and potassium carbonate (291 mg, 2.108 mmol) in tetrahydrofuran (2ml) was stirred under N2 nitrogen 15 min at room temperature. N-(4-fluoro-2- methylphenyl)azetidin-3-amine (D55) (190 mg, 1 .054 mmol) was added and the resulting mixture was stirred 1 day at room temperature. The residue obtained after solvent evaporation was purified by Biotage SNAP-Si column eluting with a mixture cyclohexane/ethyl acetate from 100/0 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D90)(155 mg)MS: (ES/+) m/z: 334.6 [MH+] C17H17F2N302 requires 333.331 H NMR (400MHz ,CHLOROFORM-d) delta = 8.24 (d, J = 2.9 Hz, 1 H), 7.80 (dd, J = 2.9, 8.3 Hz, 1 H), 6.91 – 6.75 (m, 2 H), 6.32 (dd, J = 4.9, 8.3 Hz, 1 H), 4.50 (dd, J = 7.3, 9.3 Hz, 2 H), 4.40 – 4.27 (m, 1 H), 3.97 – 3.81 (m, 5 H), 3.72 (d, J = 6.4 Hz, 1 H), 2.18 (s, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,847729-27-5, its application will become more common.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); 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. 2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine. A new synthetic method of this compound is introduced below., SDS of cas: 2897-43-0

To 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).

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, 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine.

Reference:
Patent; MERCK & CO., INC.; WO2006/31491; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19235-89-3, 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 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To isopropanol (30.0 mL) was added sodium hydride (0.606 g of 60% dispersion, 15.2 mmol) in small portions over 5 minutes. The resulting gel-like suspension was stirred for an additional 5 minutes at room temperature. 2-Chloro-4-cyanopyridine (2.00 g, 14.4 mmol) was then added in one portion and the resulting solution was heated to reflux. After 1 hour, the reaction mixture was allowed to cool to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried (magnesium sulfate) and concentrated to provide a yellow oil. Flash chromatography over silica (hexanes/ethyl acetate) afforded 1.25 g (53%) of product as a colorless oil: 1H NMR (CDCl3) delta 8.27 (d, J=5.2 Hz, 1H), 7.01 (dd, J=5.2, 1.4 Hz, 1H), 6.91 (d, J=1.4 Hz, 1H), 5.31 (sept, J=6.2 Hz, 1H), 3.33 (d, J=6.2 Hz, 6H) ppm.

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 19235-89-3, 4-Chloropyridine-2-carbonitrile.

Reference:
Patent; Genzyme Corporation; US2005/176761; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1374655-69-2, 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 1374655-69-2, name is 3-Bromo-4-ethyl-5-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 9-chloro-l-methyl-7-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-4,5-dihydro-[l,2,4] triazolo[4,3-a]quinoline (80-4; 0.717 g, 0.0020 mol) and 3-bromo-4-ethyl-5-fluoropyridine (0.423 g, 0.0020 mol) in the mixture of 1,4- dioxan (5 mL) and water (5 mL) was added sodium carbonate (0.66 g, 0.0062 mol). Reaction mass was purged with argon for the next 20 min. CatalystPd(dppf)2Cl2.dichloromethane (0.084 g, 0.0001 mol) was added and again purged with argon for 10 min and allowed to stirred at 90 C for 4 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic parts was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography followed by preparative HPLC (analytical conditions; column: ZORBAX XDB (150mm X 4.6mm X 3.5um), mobile phase (A): water, Mobile phase (B): MeOH, flow rate : 1.0 mL/min, gradient T/%B:0/20,6/25,25/75,27/20,30/20) to obtain title compound. 1H NMR (400 MHz, DMSO- d6) delta: 8.55 (s, 1 H), 8.32 (s, 1 H), 7.64 (s, 1 H), 7.55 (s, 1 H), 2.94 (bs, 4 H), 2.65-2.59 (m, 2 H), 2.56 (s, 3 H), 1.09-1.05 (t, J = 7.6 Hz, 3 H). MS (M+l): 343.2.

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 1374655-69-2, 3-Bromo-4-ethyl-5-fluoropyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2012/148808; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39856-57-0, name is 2,6-Dibromopyridin-3-amine, the common compound, a new synthetic route is introduced below. Recommanded Product: 39856-57-0

To a stirred solution of 2, 6-dibromopyridin-3-amine (38 g, 0.188 mol) in 1, 4- dioxane (400 mL) under an argon atmosphere was added sodium methoxide (70.55 g, 1.30 mol) at room temperature. The reaction mixture was stirred at reflux for 8 h. After consumption of the starting material (monitored by TLC), the reaction mixture was quenched with ice cold water (200 mL) and extracted with EtOAc (3 x 200 mL). The combined organic extracts were washed with cold water (2 x 100 mL), dried over sodium sulfate and concentrated in vacuo. The crude material was purified by column chromatography using 10% EtOAc:hexanes to afford 6-bromo-2-methoxypyridin-3-amine (13 g, 42%) as a brown solid. 1H-NMR (CDCl3, 400 MHz): delta 6.87 (d, 1H), 6.76 (d, 1H), 4.01 (s, 3H), 3.75 (br s, 2H); TLC: 20% EtOAc:hexane (Rf: 0.5).

The synthetic route of 39856-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine, molecular formula is C7H8BrNO, 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. name: 2-(Bromomethyl)-6-methoxypyridine

To a 100-mL round-bottomed flask was added 2-(bromomethyl)-6- methoxypyridine (1.33 g, 6.58 mmol), 2-(bromomethyl)-6-methoxypyridine (1.33 g, 6.58 mmol), ethyl N-(diphenylmethylene) glycinate (1.76 g, 6.58 mmol, Acros, New Jersey) and 5N sodium hydroxide (6.58 mL, 32.9 mmol) in THF (30 mL). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2 x 50 mL). The organic extract was washed with saturated NaCl (30 mL) and dried over Na2S04. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 10% EtOAc/hexanes to give ethyl N- (diphenylmethylidene)-3-(6-methoxy-2-pyridinyl)alaninate (1.86 g) as a colorless oil.

With the rapid development of chemical substances, we look forward to future research findings about 156094-63-2.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael David; BO, Yunxin; BRYAN, Marian C.; CROGHAN, Michael; FOTSCH, Christopher Harold; HALE, Clarence Henderson; KUNZ, Roxanne Kay; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis Dale; POON, Steve Fong; STEC, Markian Myroslaw; ST. JEAN, David, Joseph, Jr.; TAMAYO, Nuria A.; TEGLEY, Christopher Michael; YANG, Kevin Chao; WO2012/27261; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58481-17-7, 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 58481-17-7 as follows.

A. methyl 2-formylpyridine-4-carboxylate To a solution of methyl 2-(hydroxymethyl)pyridine-4-carboxylate (30 g, 179.64 mmol) in DCM (1 L) was added MnO2 (93.77 g. 1.0778 mol) at r.t. and stirred overnight. The reaction mixture was then filtered and concentrated to afford the title compound (21.3 g, 72%). [M+H] Calc’d for C8H7NO3, 166. Found, 166.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58481-17-7, its application will become more common.

Reference:
Patent; Quanticel Pharmaceuticals, Inc.; Kanouni, Toufike; Nie, Zhe; Stafford, Jeffrey Alan; Veal, James Marvin; US2014/275084; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem