Tag: M.W:100-200

Electric Literature of 73027-79-9, 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. 73027-79-9, name is 4,6-Dichloronicotinic acid. A new synthetic method of this compound is introduced below.

4,6-Dichloro-nicotinic acid (10.3 g, 53.4 mmol) was suspended in CH2Cl2 (200 mL). Oxalyl chloride (14 mL, 158 mmol) was added and the reaction was placed in an ice bath. DMF (1.0 mL) was added and the reaction was fitted with an air cooled condenser. The reaction was stirred for 3 h and allowed to warm to 25 C. The volatiles were removed in vacuo and the crude residue was resuspended in THF (200 mL) and cooled to 0 C. To this stirred suspension was added concentrated aqueous ammonia (75 mL) dropwise and the reaction was allowed to stir for 1 h. The volatiles were removed and the crude was redissolved in EtOAc and poured into brine. The aqueous phase was separated and extracted twice with EtOAc. The organic layers were combined, dried (Na2SO4), decanted and concentrated to afford 4,6-dichloro-nicotinamide as a beige solid (7.27 g, 71%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73027-79-9, 4,6-Dichloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/217417; (2006); 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.903522-29-2, name is 3,5-Difluoroisonicotinic acid, molecular formula is C6H3F2NO2, molecular weight is 159.09, as common compound, the synthetic route is as follows.COA of Formula: C6H3F2NO2

Synthesis of 3-Butyl-5-fluoro-isonicotinic acid [A067] 3,5-Difluoro-isonicotinic acid (0.557 g, 3.5 mmol) was suspended in anhydrous THF (8 mL) at 0C, under an atmosphere of nitrogen. To this was added butyl magnesium chloride (2.0 M in diethyl ether, 5.25 mL, 10.5 mmol) dropwise over 10 minutes. The suspension slowly changed form during the slow addition with preliminary agglomeration of solid then the solid started to dissolve slowly, achieving full solution around completion of addition of reagent. The reaction mixture was allowed to warm to room temperature and stirred over 72 hours to form a thick yellow suspension. Diluted with water and transferred into a single neck flask and concentrated in vacuo. The yellow solid was diluted with water (10 mL) and EtOAc (10 mL). The pH was adjusted pH~2, by dropwise addition of HC1 (cone.) and extracted with EtOAc (x3 – some of the yellow colour goes into organics). Combined organics were washed with brine (xl), dried (MgSC^) and concentrated in vacuo to yield the title compound [A067] as an orange gum/solid (0.402g) that solidifies slowly: NMR: (1H, 300MHz, d6-dmso); 8.52 (1H, s), 8.42 (1H, s), 2.67 (2H, t), 1.58-1.48 (2H, m), 1.35-1.22 (2H, m), 0.87 (3H, t); LCMS method: 1, RT: 1.22 min, MI 198 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,903522-29-2, 3,5-Difluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; CEPHALON, INC.; CANCER RESEARCH TECHNOLOGY LIMITED; BRESLIN, Henry, J.; DORSEY, Bruce, D.; DUGAN, Benjamin, J.; FOWLER, Katherine, M.; HUDKINS, Robert, L.; MESAROS, Eugen, F.; MONCK, Nathaniel, JT; MORRIS, Emma, L.; OLOWOYE, Ikeoluwa; OTT, Gregory, R.; PAVE, Gregoire, A.; ROFFEY, Jonathan, R. A.; SOUDY, Christelle, N.; TAO, Ming; ZIFICSAK, Craig, A.; ZULLI, Allison, L.; WO2014/52699; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79055-62-2 ,Some common heterocyclic compound, 79055-62-2, molecular formula is C6H7ClN2, 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 mixture of tert-butyl nitrite (150 mL, 1262 mmol) in acetonitrile (1000 mL) was added copper(II) bromide (226 g, 1010 mmol) at 30 C. The solution was then stirred at 22 C for 40 min and then cooled to 0 C. A solution of 2-chloro-5-methylpyridin-4-amine (120 g, 842 mmol) in acetonitrile (500 mL) was added at 0 C. The reaction was stirred at 0 C for 1 h and then warmed to 22 C and stirred for 12 h. The resulting mixture was concentrated in vacuum. The residue was dissolved in DCM (2000 mL), washed with aqueous NH3 (15%, 2000 mL), dried over anhydrous Na2S04, and filtered. The filtrate was concentrated in vacuum and the resulting residue was purified by flash silica gel chromatography (eluting with ethyl acetate/pet. ether gradient) to give 4-bromo-2-chloro-5-methylpyridine as colorless oil. MS: 206 / 208 (M + 1 / M + 3). 1H MR (400 MHz, CDC13) delta 8.14 (s, 1H), 7.48 (s, 1H), 2.30 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,79055-62-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CTXT PTY. LTD.; MACHACEK, Michelle, R.; WITTER, David, J.; REUTERSHAN, Michael Hale; ALTMAN, Michael, D.; STUPPLE, Paul Anthony; (67 pag.)WO2019/94311; (2019); 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. 181123-11-5, name is 5-Chloro-2-cyano-3-nitropyridine, the common compound, a new synthetic route is introduced below. Product Details of 181123-11-5

To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta 7.88 (br. s, 1H), delta 7.73 (s, 1H), delta 7.39 (br. s, 1H), delta 7.23 (s, 1H), delta 7.06 (br. s, 2H). LC/MS (ESI+) m/z=172 (M+H).

The synthetic route of 181123-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 126832-81-3, 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 126832-81-3 as follows.

27c) 1-(4-Pyridyl)-4-piperidone Hydrazone Hydrazine monohydrate (1 ml) was added to a solution of 1-(4-pyridyl)-4-piperidone (1.76 g) in methanol (18 ml), and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off, and the residue was crystallized with methanol-ether to obtain the title compound as pale yellow crystals (1.76 g, 92%). NMR (CDCl3) delta: 2.50 (2H, t, J=6.2), 2.61 (2H, t, J=6.2), 3.54 (2H, t, J=6.2), 3.63 (2H, t, J=6.2), 4.99 (2H, bs), 6.60 (2H, d, J=6.6), 8.27 (2H, d, J=6.6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,126832-81-3, its application will become more common.

Reference:
Patent; Kubo, Keiji; Miyawaki, Toshio; Kawamura, Masaki; US2003/187023; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 932-35-4, 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 932-35-4, name is 3-Hydroxypicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-hydroxypyridine-2-carbonitrile d (10 mmol, 1.2 g), chloroacetone (1 equiv. , 10 mmol, 0.93 g) and potassium carbonate (1 equiv., 10 mmol, 1.38 g) in DMF (30 ml) was heated at 80C overnight. The reaction mixture was poured into ice-water (200 ml) and the precipitate was filtered off and dried to afford intermediate e (1.4 g, yield = 80%, purity (LC) > 95%). To a stirred mixture of intermediate e (7.9 mmol, 1.39 g) and cyanoacetic acid (1 equiv. , 7.9 mmol, 0.675 g) in DMF (20 ml) was added EDCI (1 equiv. , 7.9 mmol, 1.51 g) and the reaction mixture was stirred overnight at room temperature. The mixture was poured into ice-water (150 ml) causing a precipitation. The solid was filtered off and dried by co-evaporation with tetrahydrofuran and then with toluene. The residue was mixed with isopropanol (15 ml) and ethyl-diisopropylamine (1 equiv., 7.9 mmol, 1.02 g) and heated to 80C during 4h. After cooling to room temperature, a solid was filtered off affording intermediate f (1.35 g, yield = 76%, purity (LC) > 95%). A mixture of intermediate f (1.0 mmol, 0.225 g), copper (II) acetate(2 equiv. , 2.0 mmol, 0.363 g), 4-nitrophenylboronic acid (2.0 equiv. , 2.0 mmol, 0.334 g), triethyl- amine (2.0 equiv. , 2.0 mmol, 0.202 g) and pyridine (2.0 equiv. , 2.0 mmol, 0.158 g) in dichloromethane (5 ml) was stirred overnight at room temperature in a reaction vial provided with a calcium chloride tube. The reaction mixture was dilluted with dichloromethane (50 ml), washed with water, dried (MgS04), filtered and evaporated under reduced pressure. The crude compound was purified by chromatography (silica gel, eluent: 2% methanol in dichloromethane) to afford compound 3 (30 mg, yield = 8 %, purity (LC) = 82 %).

According to the analysis of related databases, 932-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS Ltd.; WO2005/111044; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74420-15-8 ,Some common heterocyclic compound, 74420-15-8, molecular formula is C7H5BrN2, 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.

[0193] In a microwave tube was placed ethyl 2-bromothiazole-4-carboxylate (944 mg, 4 mmol), 3-bromo-1H-pyrrolo[2,3-blpyridine (867 mg, 4.40 mmol), and K2C03 (663 mg, 4.80 mmol). The tube was sealed and DMSO (7.5 ml) was added. The mixture was heated at 150C for 3 h. The mixture was poured into EtOAc/H20 (30 mL/30 mL). The organic was dried (Na2504) and filtered. After removal of the solvent, the product was purified (twice) by silica gel chromatography using 10-20% EtOAc/hexane as the eluent to give ethyl 2-(3- bromo- 1 H-pyrrolo[2,3 -blpyridin- 1 -yl)thiazole-4-carboxylate (587 mg, 1.667 mmol, 41.7% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74420-15-8, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1060811-62-2, 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.1060811-62-2, name is 4,6-Dichloronicotinaldehyde, molecular formula is C6H3Cl2NO, molecular weight is 176, as common compound, the synthetic route is as follows.

To a reaction vessel containing a mixture of 4,6-dichloronicotinaldehyde (300 g, 1.7 mol) in 1,4- dioxane (1200 mL) was added hydrazine (50%> in water)(360 mL, 3.6 mol). The reaction vessel was sealed and heated at 150 C over 18 h. The mixture was cooled to room temperature, concentrated in vacuo, poured over water and filtered. The filter cake was washed with 20%> EtOAc in hexanes and dried to afford 6-chloro-lH-pyrazolo[4,3-c]pyridine (101.4 g, 38 %>) as a light-yellow solid. LCMS (ESI) [M+H]+ = 154.

The chemical industry reduces the impact on the environment during synthesis 1060811-62-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; DIEDERICH, Francois; DOTSON, Jennafer; HANAN, Emily; HEFFRON, Timothy; LAINCHBURY, Michael; HEALD, Robert; SEWARD, Eileen M.; WO2014/210354; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84249-14-9, 2-Amino-4-bromopyridine, 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, Quality Control of 2-Amino-4-bromopyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Amino-4-bromopyridine

Step 1: N-(4-bromopyridin-2-yl)acetamide To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol). The reaction mixture was allowed to stir at 140 C. for 3 h and then allowed to cool to rt. Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH. The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g, 89%) as a white solid.

The synthetic route of 84249-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); 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 5470-70-2, name is Methyl 6-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 1: Intermediate 31-b [0181] To a solution of methyl 6-methylnicotinate 31-a (20.10 g, 133 mmol) in THF (90 ml) cooled to 0° C. was added drop wise a 1.0 M solution of LiAlH4 in THF (100 ml, 100 mmol) and the reaction was then stirred at 0° C. for 1 hour. Water (3.8 ml) was slowly added, followed by 15percent NaOH (3.5 ml) and water (11.4 ml) and the mixture was stirred at room temperature for 1 hour. The reaction was filtered over celite and volatiles were removed in vacuo to provide intermediate 31-b as a yellow oil.

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; Pharmascience, Inc.; Laurent, Alain; Rose, Yannick; Jaquith, James B.; US2015/191473; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem