Month: April 2022

Electric Literature of 1227489-68-0 ,Some common heterocyclic compound, 1227489-68-0, molecular formula is C7H5F3N2O2, 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 2-amino-4-(trifluoromethyl)nicotinic acid (74.0 mg, 0.359 mmol) and 50% aq. chloroacetaldehyde (0.093 mL, 0.718 mmol) was heated to 80 C for 18 h. The reaction mixture was concentrated in vacuo to yield the title compound. MS: m/z = 231 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227489-68-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott; COOKE, Andrew; STUMP, Craig; WILLIAMS, Peter; WO2014/113303; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1 ,Some common heterocyclic compound, 1111637-74-1, molecular formula is C7H5BrFNO, 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.

Step 1: (R,Z)-N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide (5b) A mixture of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (5a, synthesized according to procedures described in WO2009016460; 11 g, 50.5 mmol), (R)-2-methylpropane-2-sulfinamide (Ak Scientific, 12.23 g, 101 mmol) and titanium (IV) ethoxide (Aldrich, 26.1 ml, 126 mmol) in THF (100 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature, and brine (200 mL) was added. The suspension was vigorously stirred for 10 min. The suspension was filtered through a pad of silica gel and the organic phase was separated. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (gradient 0-20% EtOAc/hexanes) to afford the title compound as a bright yellow oil (16 g, 49.8 mmol, 99% yield). MS m/z=320.8 [M+H]+; Calculated for C11H14BrFN2OS: 320.0

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. 1111637-74-1, 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 68175-07-5, Adding some certain compound to certain chemical reactions, such as: 68175-07-5, name is 2-Methyl-1H-imidazo[4,5-b]pyridine,molecular formula is C7H7N3, 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 68175-07-5.

2-methyl-3H-imidazo[4,5-bjpyridine (10.8 g, 81 mmol) was mixed in EtOAc (500 mL) to give a partial suspension and mCPBA (18.66 g, 81 mmol) was added in portionsover 15 minutes. The resulting mixture was stirred at rt for 1.5 h. LCMS analysis indicated reaction was only 85percent complete, therefore an addition amount of mCPBA (2.2 g) was added. After stirring an additional 30 mm at a, the resulting precipitate which had formed was collected by filtration, rinsed with additional cold EtOAc (50 mL x 3) and dried under vacuum to afford 12 g (99percent) of the desired product as a tan solid.?H NMR (400 MHz, METHANOL-d4): oe 8.24 (dd, J=6.4, 0.7 Hz, 1H), 7.74 (d, J7.9 Hz,1H), 7.31 (dd, J=8.1, 6.4 Hz, 1H), 2.67 (s, 3H).

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. 68175-07-5, 2-Methyl-1H-imidazo[4,5-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WROBLESKI, Stephen T.; WEINSTEIN, David S.; YANG, Michael G.; (73 pag.)WO2018/81488; (2018); 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. 2739-98-2, name is Ethyl 2-Pyridylacetate, the common compound, a new synthetic route is introduced below. COA of Formula: C9H11NO2

1b) 2-Hydroxypyrazolo[1,5-a]pyridine (C4f); The synthesis of 2-hydroxypyrazolo[1,5-a]pyridine was done according to literature (Ochi, M.; Miyasaka, T.; Kanada, K.; Arakawa, K. Bull. Chem. Soc. Japan, (1976), 49, 1980-1984).; A solution of 4.14 g (36.6 mmol) hydroxylamine-O-sulfonic acid in 13.8 ml water was neutralized with KOH (2.6 N) at 0C and added dropwise to 26.2 ml (0.172 mol) ethyl 2-pyridylacetate. After stirring for 30 h at room temperature the mixture was extracted with dichloromethane, the aqueous layer was adjusted to pH 9 with Na2CO3 solution (10%) and extracted with dichloromethane. Then, the aqueous layer was adjusted to pH 5 with acetic acid, extracted with dichloromethane, the organic layer was dried with MgSO4 and evaporated. The crude product was purified by flash-chromatography (hexane/EtOAc 90:10). Yield: 607 mg (39 %) white solid. Mp.: 127-128C. MS (APCI): m/z 135 (M+1)+. 1H NMR (DMSO-d6, 360 MHz) delta (ppm): 5.72 (d, J = 0.8 Hz, 1 H, H-3); 6.63 (ddd, J = 6.8 Hz, 6.8 Hz, 1.4 Hz, 1 H, H-6); 7.08 (ddd, J = 8.9 Hz, 6.8 Hz, 1.1 Hz, 1 H, H-5); 7.35 (ddd, J = 8.9 Hz, 1.4 Hz, 0.8 Hz, 1 H, H-4); 8.32 (dd, J = 6.8 Hz, 1.1 Hz, 1 H, H-7); 10.40 (s, 1 H, OH).

The synthetic route of 2739-98-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHWARZ PHARMA AG; EP1972628; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 76006-11-6, 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.76006-11-6, name is 7-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Pyrazolopyridine 6 (0.44 g, 2.9 mmol) was dissolvedin dry methanol (50 mL) and N-iodosuccinimide (1.0 g,4.4 mmol) was added in portions. The mixture was stirred atroom temperature for 2h. Then, the solvent was removedunder reduced pressure and the residue was extracted withethyl acetate. The combined organic extracts were washedwith aqueous sodium thiosulfate (10% w/v) solution, thendried over sodium sulfate, filtered and concentrated. Thecrude product was purified by column chromatography (silicagel) using a mixture of cyclohexane/ethyl acetate (6/4,v/v) as the eluent to provide pure 7 as a yellow solid, in 99% yield. mp 252-3 C (EtOAc). 1H NMR (600 MHz, DMSO-d6) 7.50 (d, 1H, H-4, J = 5.5Hz), 8.08 (d, 1H, H-5, J =5.5Hz). HR-MS (ESI) m/z: calcd for C6H4ClIN3, [M1+H]+ =279.9133, found 279.9128. Anal. Calcd for C6H3ClIN3: C,25.79; H, 1.08; N, 15.04. Found: C, 25.91; H, 1.13; N, 14.88.

Statistics shows that 76006-11-6 is playing an increasingly important role. we look forward to future research findings about 7-Chloro-1H-pyrazolo[3,4-c]pyridine.

Reference:
Article; Gavriil, Efthymios-Spyridon; Lougiakis, Nikolaos; Pouli, Nicole; Marakos, Panagiotis; Skaltsounis, Alexios-Leandros; Nam, Sangkil; Jove, Richard; Horne, David; Gioti, Katerina; Pratsinis, Harris; Kletsas, Dimitris; Tenta, Roxane; Medicinal Chemistry; vol. 13; 4; (2017); p. 365 – 374;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 849068-61-7, 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 849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 1; Methyl 5-bromo-l/7-pyrrolo [2,3-/>] pyridine-3-carboxylate; A solution of 5-bromo-l//-pyrrolo[2,3-6]pyridine (0.200 g, 1.01 mmol; described in: Mazeas,D. et al, Heterocycles 1999, 50, 1065-1080) in dichloromethane (12 mL) was added to asuspension of aluminum chloride (0.704 g, 5.28 mmol) in dichloromethane (5 mL) under anatmosphere of nitrogen. The resulting mixture was stirred at room temperature for 40 min togive a brownish solution. Trichloroacetyl chloride (0.56 mL, 5.0 mmol) was added and themixture was stirred at room temperature for 17 h. Methanol (10 mL) was added and thesolvent was evaporated in vacuo. The residue was treated with aqueous potassium hydroxide(3 M, 10 mL) and methanol (5 mL) and heated at 60 C for 1 h and 15 min. The mixture wasallowed to cool to room temperature and the pH was adjusted to 1-2 using aqueoushydrochloric acid (2 M). The aqueous phase was extracted with ethyl acetate, dried oversodium sulfate, and the solvent was evaporated to give a brown residue. Acetyl chloride (10mL) was added dropwise to cooled methanol (0 C, 20 mL). The resulting solution was addedto a solution of the brown residue in methanol (10 mL) at room temperature, and the resultingmixture was heated at reflux for 3 h. The mixture was allowed to cool to room temperatureand the solvent was evaporated to give a yellow solid. The crude product was purified on asilica gel column using a gradient, ethyl acetate/heptane mixture (10, 20, 30,40, 50% ethylacetate), as the eluent to give 0.165 g (64% yield) of the title compound as a pale pink solid:’H NMR (DMSO-d6, 300 MHz) 5 12.80 (br s, 1 H), 8.41 (s, 2 H), 8.30 (d, J= 3.0 Hz, 1 H),3.83 (s, 3 H); 13C NMR (DMSO-d6, 75 MHz) 6 163.9, 147.0, 144.1, 134.5,130.5, 119.6,113.1, 105.0, 51.1; MS (ES) m/z 255 and 257 (M++l).

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 849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; WO2006/1754; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 274-76-0, 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.274-76-0, name is Imidazo[1,2-a]pyridine, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

a) Imidazo [1, 2-a] pyridine-3-carbaldehyde; Imidazo [1, 2-a] pyridine (0.500 g, 4.23 mmol) was dissolved in 1 mL of DMF and phosphorus oxychloride (0.71 g, 4.6 mmol) was added dropwise and the mixture was stirred and checked on LC-MS. After lh the mixture was poured into water and made alkaline with 1M NaOH. The mixture was extracted three times with EtOAc and the combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel with DCM: MeOH 99: 1-96: 4. Yield: 83 mg (13%). ‘H NMR (300 MHz, CDCl3) 6 9.95 (s, 1H), 9.50 (m, 1H), 8.32 (s, 1H), 7.80 (m, 1H), 7.56 (m, 1H), 7.13 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 274-76-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2005/66132; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5444-01-9, 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.5444-01-9, name is 4-Methylnicotinonitrile, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

1M LiHMDS (45mL, 44.794mmol) was added to a solution of 4- methylnicotinonitrile (2.52g, 21.33mmol) in THF (15mL) at -78C and the resulting reaction mass was stirred at -78C for 1 hour. This was followed by the addition of dimethyl carbonate (1.98mL, 23.464mmol) and stirred the resulting reaction mass at – 78C for 1 hour and further at 0C for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was quenched with saturated NH4C1 solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (25% ethyl acetate in hexane) afforded 530 mg of the product (14.10% yield).1H NMR (300 MHz, CDC13): delta 8.9 (s, 1H), 8.79 (d, 1H), 7.4 (d, 1H), 3.9 (s, 2H), 3.79 (s, 3H)

The chemical industry reduces the impact on the environment during synthesis 5444-01-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; MOEBITZ, Henrik; SENGUPTA, Saumitra; WO2012/35078; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88912-24-7, 5,6-Dichloropicolinic 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, 88912-24-7, blongs to pyridine-derivatives compound. Recommanded Product: 88912-24-7

Sodium hydride (CAN 7646-69-7, 60% w/w, 1.05 g, 26 mmol) was added tocyclopropylmethanol (CAN 2516-33-8, 7.5 g) at 0C and the mixture was stirred for 1 h. 5,6-Dichloro-pyridine-2-carboxylic acid (1 g, 5 mmol) was added and the mixture was heated to 95C for 3 h. The solvent was removed under reduced pressure. The residue was diluted with water (10 mL) and adjusted to pH = 3.0 by hydrochloric acid (3 N). The solution was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with water (3 x 30 mL) and brine (2 x 40 mL) and evaporated to dryness to give the crude product (0.35 g, 25%>), which was used in the next step without further purification, MS (EI): m/e = 228.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,88912-24-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58819-88-8, 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 58819-88-8 as follows.

To an oven-dried 40 mL vial was added 6-bromo-2-methoxynicotinaldehyde, dichloromethane (0.5M), and (R)-2-methylpropane-2-sulfmamide (1.0 equiv.) at room temperature. To the vial was then added titanium tetraethoxide (2.0 equiv.). The mixture was stirred overnight before being diluted with sodium bicarbonate solution. The contents of the vial were filtered through celite, and the filtrate was washed once with water and once with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography using hexanes/ethyl acetate gradient to yield (R,E)-N-((6-bromo-2-methoxypyridin-3-yl)methylene)-2-methylpropane-2- sulfmamide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58819-88-8, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (300 pag.)WO2019/204609; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem