Day: April 15, 2022

Adding a certain compound to certain chemical reactions, such as: 1190862-70-4, Ethyl 5-bromo-6-methylnicotinate, 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, 1190862-70-4, blongs to pyridine-derivatives compound. Formula: C9H10BrNO2

2M Aqueous sodium hydroxide solution (1.91 mL, 3.8 mmol) was added to a stirred solution of ethyl 5-bromo-6-methylnicotinate (preparation 47c, 0.41 g, 1.7 mmol) in ethanol (14 mL) at room temperature. After 3 hours, the solvent was evaporated and water was added to the residue. The pH was adjusted to 4-5 with concentrated hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4) and evaporated to give the title compound (0.16 g, 43%) as a white solid. LRMS (m/z): 216/218 (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,1190862-70-4, its application will become more common.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 849068-61-7, 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. 849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, molecular formula is C8H5BrN2O2, 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.

Example 108 5-BROMO-LH-PYRROLO [2, 3-B] PYRIDINE-3-CARBOXYLIC acid (2,3-difluoro-phenyl)-amide [0329] To a suspension of 5-BROMO-LH-PYRROLO [2, 3-B] PYRIDINE-3-CARBOXYLIC acid (950 mg, 3.94 mmol) in DCM (20 mL) and DMF (0.1 mL) was added oxalyl chloride (600 mg, 4.72 mmol) slowly. The mixture was stirred at RT for 1 h. To this suspension was then added a solution of 2,3-difluorophenyl amine (610 mg, 4.72 mmol) and triethylamine (800 mg, 7.91 mmol) in DCM (5 mL). The reaction was kept at RT for another 2 h. The solvent was then evaporated, the residue was washed water, and dried for direct use. MS (ES+): m/e= 352 (M+H); LC : 3.5 min.

According to the analysis of related databases, 849068-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2005/28475; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 109306-86-7 ,Some common heterocyclic compound, 109306-86-7, 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.

2-(2-bromophenyl)pyridine (312 muL, 1.83 mmol) was added to [IrCl(cyclooctene)2]2 (1) (400 mg, 0.446 mmol), in 10 mL of 2-ethoxyethanol. The mixture was stirred overnight at reflux (135 C.) leading a yellow suspension, which was dried under vacuum and the residue treated with 3*5 mL of diethylether to afford 581 mg of an insoluble yellow powder. HR-MS (MALDI-TOF; DMSO): m/z calcd. for [C22H14Br2IrN2] 658.9, found: 658.4. Calcd. for [C22H15BrIrN2]: 579.0, found: 579.1. Calcd. for [C22H16IrN2]. Acetylacetone (67.4 muL, 0.666 mmol) and KOH (44.0 mg, 0.666 mmol) in 2 mL of methanol was added to the yellow powder (439.5 mg, 0.317 mmol) in 15 mL of THF. The mixture was stirred at 60 C., for 90 min, in a closed system. Then, the solvent was removed under vacuum and the residue was treated with 15 mL of CH2Cl2. The resulting suspension was filtered over Celite to afford a yellow solution, which was concentrated almost to dryness under vacuum. The addition of 5 mL pentane led to a yellow solid, which was washed with 2*4 mL pentane and dried under vacuum. The solid (a mixture of compounds 5, 6, and 7) was purified by silica column chromatography using toluene-pentane-ethyl acetate (1-3-1) as eluents. Yield: 180.6 mg (42%). The desired tris-heteroleptic compound 6 is obtained with 82% selectivity. Anal. Calcd for C27H22BrIrN2O2: C, 47.79; H, 3.27; N, 4.13. Found: C, 47.78; H, 3.66; N, 4.16.

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. 109306-86-7, 2-(2-Bromophenyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Universal Display Corporation; Tsai, Jui-Yi; Boudreault, Pierre-Luc T.; Mora, Erik; (175 pag.)US2020/111976; (2020); 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. 1370347-50-4, name is (S)-1-(3,5-Dichloropyridin-4-yl)ethanol. A new synthetic method of this compound is introduced below., Recommanded Product: (S)-1-(3,5-Dichloropyridin-4-yl)ethanol

Dissolve (S)- l-(3,5-dichloropyridin-4-yl)ethanol (5.02 g, 26.14 mmol) in dichloromethane (DCM, 100 mL) and cool the flask in an ice bath. Add triethylamine (TEA, 3.5 mL, 25.11 mmol) followed by the dropwise addition of methanesulfonyl chloride (2.2 mL, 28.42 mmol). Remove the ice bath and allow the reaction to warm to RT. After 4 hours, quench the reaction with water (100 mL) and separate layers. Extract the aqueous layer with DCM (50 mL) followed by 20% isopropyl alcohol (IPA)/chloroform (50 mL). Combine the organic extracts, dry over anhydrous sodium sulfate, filter and concentrate in vacuo. Yield: 7.15 g, (100%). MS (ES) m/z 270 [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, 1370347-50-4, (S)-1-(3,5-Dichloropyridin-4-yl)ethanol.

Reference:
Patent; ELI LILLY AND COMPANY; CHEN, Daohong; LI, Hong-Yu; ZHAO, Genshi; WO2010/129509; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 185017-72-5, 3-Bromo-2-chloro-6-picoline, 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, 185017-72-5, blongs to pyridine-derivatives compound. Computed Properties of C6H5BrClN

a) l-(2-Chloro-6-methylpyridin-3-yl)cyclobutanol A suspension of molecular sieves (4 A) and 3-bromo-2-chloro-6-methylpyridine (CAN 185017-72-5, 5 g, 24.2 mmol) in THF (50 mL) was cooled to -15 C. 1.3 M isopropyl magnesium chloride lithium chloride complex solution in THF (19.6 mL, 25.4 mmol) was added within 30 min. Stirring was continued for 1 h at -15 C. Cyclobutanone (1.87 g, 2.00 mL, 26.6 mmol) was slowly added. Stirring was continued for 2 h at -15 C and for further 2 h at 0 C. Water (2.5 mL) was added, the mixture was concentrated in vacuo, and poured onto sat. aqueous NH4C1 solution. The mixture was extracted with EtOAc (2 x 100 mL). The combined extracts were washed with ice water (50 mL), dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 140 g, heptane / EtOAc 0-40% in 120 min.) to give the title compound (3.33 g, 70%) as white solid, MS (ESI): m/e = 198.1 [MH+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,185017-72-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BENDELS, Stefanie; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHAFFTER, Ernst; SCHULZ-GASCH, Tanja; WO2014/86806; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92992-85-3, 2-Bromo-3,5-dimethylpyridine, 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, name: 2-Bromo-3,5-dimethylpyridine, blongs to pyridine-derivatives compound. name: 2-Bromo-3,5-dimethylpyridine

To a solution of 2-bromo-3,5-dimethylpyridine (2.0 g)in tetrahydrofuran (30 mL) was added under cooling at-78c 1.59 M n-butyllithium/hexane solution (7.04 mL) and the mixture was stirred for 1 hr. A solution of 1-(tert-butoxycarbonyl)-4-piperidone (2.23 g)in tetrahydrofuran (40 mL) was added, and the mixture was stirred at-78c for 30 min. The reaction mixture was heated to room temperature,saturated aqueous sodium carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine,dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane:ethyl acetate) and NH column chromatography (hexane:ethyl acetate)to give 4′-hydroxy-3,5-dimethyl-3′,4′,5′,6′-tetrahydro-2’H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (1.69 g).

The synthetic route of 92992-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 99368-68-0, 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 99368-68-0 as follows.

A solution of 6-chloro-5-(trifluoromethyl)pyridin-3-amine (0.35 g, 1.78 mmol) in acetic anhydride (6 mL) was heated at 100 C. for 12h. The solution was evaporated until dryness. The residue was taken up in DCM. The organic layer was washed with a 10% aqueous solution of K2CO3, separated, dried over MgSO4, filtered and evaporated to give a crude product (0.44 g, 100%). This compound was used directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99368-68-0, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; LU, Tianbao; CONNOLLY, Peter J.; CUMMINGS, Maxwell David; DIELS, Gaston Stanislas Marcella; THURING, Jan Willem; PHILIPPAR, Ulrike; EDWARDS, James Patrick; BERTHELOT, Didier Jean-Claude; WU, Tongfei; (65 pag.)US2019/381012; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 156094-63-2, Adding some certain compound to certain chemical reactions, such as: 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine,molecular formula is C7H8BrNO, 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 156094-63-2.

[00602] A 60 % dispersion of sodium hydride in mineral oil (0.019 g, 0.493 mmol) was added to a stirred solution of 2-(phenoxymethyl)-6,7-dihydropyrazolo[l,5-a]pyrazin- 4(5H)-one (0.1 g, 0.411 mmol) in DMF (4 mL) at 0 C. The mixture was stirred at room temperature for 15 min. Then 2-bromomethyl-6-methoxypyridine (0.99 g, 0.493 mmol) was added and the mixture was stirred at room temperature for 16 h. The mixture was cooled at 0 C, treated with water and extracted with AcOEt. The organic layer was separated, washed with brine, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash chromatography (silica; EtOAc in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to afford an impure product that was repurified by flash column chromatography (silica; DCM). The desired fractions were collected and the solvents evaporated in vacuo. The desired product was triturated with diethyl ether and filtered to yield 5-[(6-methoxypyridin-2-yl)methyl]-2-(phenoxymethyl)-6,7- dihydropyrazolo[l,5-a]pyrazin-4(5H)-one (0.105 g, 70.5% yield). C2oH2oN403 *H NMR (400 MHz, CDC13) delta ppm 3.87 (s, 3 H) 3.90 – 3.98 (m, 2 H) 4.37 – 4.44 (m, 2 H) 4.76 (s, 2 H) 5.09 (s, 2 H) 6.65 (d, J=8.1 Hz, 1 H) 6.90 (d, J=7.2 Hz, 1 H) 6.93 – 7.04 (m, 4 H) 7.26 – 7.33 (m, 2 H) 7.54 (dd, J=8.2, 7.3 Hz, 1 H).

According to the analysis of related databases, 156094-63-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P., Jeffrey; LINDSLEY, Craig, W.; STAUFFER, Shaun, R.; BARTOLOME-NEBREDA, Jose Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; TONG, Han Min; ALCAZAR-VACA, Manuel Jesus; ANDRES-GIL, Jose Ignacio; WO2013/192350; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 670253-37-9 ,Some common heterocyclic compound, 670253-37-9, molecular formula is C5H4ClIN2, 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 suspension of 4-chloro-5-iodopyridin-2- amine (2.54 g, 10.0 mmol), sodium thiomethoxide (1.40 g, 20.0 mmol), copper(l) iodide (190 mg, 1.00 mmol), potassium carbonate (2.76 g, 20.0 mmol) and ethylene glycol (1.12 ml_, (1026) 20.0 mmol) in I PA (3 ml_) was stirred at 80 C under an N2 atmosphere for 19 h. The reaction mixture was allowed to cool to rt, filtered through Celite and the solids were washed using MeOH (3 x 20 ml_). The combined filtrates were concentrated under reduce pressure and water (30 ml_) was added to the residue. The resulting suspension was extracted with DCM (3 x 20 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash (1027) chromatography (20%; then 30%; then 40% EtOAc in cyclohexane (isocratic)) to give the title compound (779 mg, 44%) as an off-white crystalline solid. LCMS (Method A): RT = (1028) 0.41 min, m/z = 175, 177 [M+H]+. 1 H NMR (500 MHz, DMSO-cfe): d 8.01 (s, 1 H), 6.59 (s, 1 H), 6.34 (s, 2H), 2.32 (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. 670253-37-9, 4-Chloro-5-iodopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ROUNTREE, James Samuel Shane; WHITEHEAD, Steven Kristopher; TREDER, Adam Piotr; PROCTOR, Lauren Emma; SHEPHERD, Steven David; BURKAMP, Frank; COSTA, Joana Rita Castro; O’DOWD, Colin; HARRISON, Timonthy; (333 pag.)WO2019/150119; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1227594-89-9, 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 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Step 8(f): 3-fluoro-1-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridin-2(1 H)-one (8-8) To a solution of 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (8-5; 50 mg; 0.34 mmol) in dioxane 1.7 mL) was added K2CO3 (51 mg; 0.373 mmol) and the mixture was stirred for 5minutes. 5-(chloromethyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (8-4; 68 mg; 0.373 mmol) was then added, and the mixture was stirred for 2 hours at room temperature. The mixture was diluted with water, and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and concentrated in vacuo. Purification by ISCO CombiFlash provided the title compound. 1H NMR (400 MHz, CDCl3): delta 10.14 (s, 1 H); 8.11 (d, J=5.2 Hz, 1 H); 7.18 (t, J=4.7 Hz, 1 H); 5.40 (s, 2 H); 3.41 (s, 3 H).

According to the analysis of related databases, 1227594-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Burch, Jason; Cote, Bernard; Nguyen, Natalie; Li, Chun Sing; St-Onge, Miguel; Gauvreau, Danny; US2011/245296; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem