Category: pyridine-derivatives

Electric Literature of 153034-94-7, 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 153034-94-7, name is 2-Fluoro-4-iodo-5-picoline. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 3; 5-Bromomethyl-2-fluoro-4-iodo-pyridine; In a flask, combine 2-fluoro-4-iodo-picoline (10.0 g, 42.19 mmol), N- bromosuccinimide (9.76 g, 54.85 mmol), 2, 2′-azobisisobutyronitrile (3.46 g, 21.10 mmol) and dry CCl4 (100 mL). Heat at 70 0C under nitrogen for 16 hours. Cool to room temperature. Dilute with dichloromethane and wash with water and saturated aqueous sodium chloride. Separate the layers and dry the organic layer over magnesium sulfate. Concentrate in vacuo to give crude product. Purify by column chromatography (1 % to 15 % ethyl acetate in hexane) to afford the title compound (8.27 g, 62 %). MS (EI) m/z 315M+.

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 153034-94-7, 2-Fluoro-4-iodo-5-picoline.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 7205-46-1, Adding some certain compound to certain chemical reactions, such as: 7205-46-1, name is 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine,molecular formula is C7H6ClN3, 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 7205-46-1.

6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (2.52 g, 0.015 mol) was stirred with 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.86 g, 0.0015 mol), sodium-tert-butoxide (2.16 g, 0.0225 mol) and 4-(4-methoxybenzyloxy)-2-methylaniline (3.68 g, 0.015 mol) in dry dioxane (50 mL) under N2 (g) for 30 minutes. Tris(dibenzylideneacetone)dipalladium(0) (0.68 g, 0.00075 mol) was added and the mixture was stirred at 100C for 4.5 h. The mixture was concentrated in vacuo and the residue was treated with water (50 mL) and extracted into EtOAc (2 x 300 mL). The combined extracts were washed with brine, dried (MgSO i), filtered and concentrated in vacuo to give a solid which was recrystalised from isopropanol to give the desired compound. [00306] NMR delta (ppm)(DMSO-d6): 8.43 (1 Eta, d, ArH), 7.98 (1 H, s, NH), 7.75 (1 H, s, ArH), 7.39 (2 H, d, ArH), 7.27 (1 H, d, ArH), 7.00-6.90 (3 H, m, ArH), 6.82 (1 H, dd, ArH), 6.38 (1 H, d, ArH), 5.00 (2 H, s, CH), 3.77 (3 H, s, CH3), 3.64 (3 H, s, CH3), 2.17 (3 H, s, CH3).

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. 7205-46-1, 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; MENET, Christel; SCHMITT, Benoit; GENEY, Raphael; DOYLE, Kevin; PEACH, Joanne; PALMER, Nicholas; JONES, Graham; HARDY, David; DUFFY, James; WO2013/117649; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 67139-79-1 ,Some common heterocyclic compound, 67139-79-1, molecular formula is C7H4Cl2N2, 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 2; Synthesis of 4-(2 4-Dichloro-benzeloxy)-5-(2, 4-dichloro-benzyloxamethyl .- 2- (4, 6-dichloro-pyrrolo [3, 2-c] pyridin-1-yl-3-methyl-tetrahydro-furan-3-ol; To a solution of the base prepared in step 1 above (1.01 g, 5.4 mmol) in 150 mL anhydrous acetonitrile under argon at room temperature was added sodium hydride (60%, 260 mg, 6.5 mmol). The solution was allowed to stir for 4 h. To a solution of the ss-D-1-O-methyl-2, 3, 5,-tri (2,4-dichlorobenzyl)-ribofuranose (sugar Y) (1.11 g, 2.2 mmol) in 75 mL anhydrous dichloromethane under argon at 0C was added 0.86 mL HBr (30%) dropwise. The resulting solution was allowed to stir at 0 for 1 h and then at room temperature for 3 h. The solution was then evaporated in vacuo and coevaporated with toluene. The residue was dissolved in 50 mL anhydrous acetonitrile and added to the solution of the sodium salt of base prepared in Step 1 above. The combined mixture was stirred at room temperature for 24 h, and then evaporated to dryness. The residue was dissolved in EtOAc, and washed with water. The water was extracted 3x with EtOAc. The combined organic extracts were washed with brine and dried with Na2S04. The solvent was removed in vacuo. Column chromatography with silica gel using 30% ethyl acetate in hexane was used for final purification. The title nucleoside was isolated as a dark brown oil (724.3 mg, 51%).

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. 67139-79-1, 4,6-Dichloro-1H-pyrrolo[3,2-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENELABS TECHNOLOGIES, INC.; WO2003/93290; (2003); A2;,
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 1122-71-0, name is 6-Methyl-2-pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

A mixture of 6-methyl-2-pyridylmethanol (145 mg, 1.17 mmol) and sodium hydroxide (63 mg, 1.57 mmol) in benzene (15 mL) was heated to reflux for 3 hours with stirring under nitrogen atmosphere and then cooled to 25 C. followed by the addition of compound 133 (0.30 g, 0.785 mmol) at same temperature. The mixture was heated to reflux for 12 hours, concentrated under vacuum and diluted with water (20 mL). The mixture was then extracted with EtOAc (2*20 mL). The combined organic layers were washed with water (2*10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. The residue thus obtained was purified by column chromatography (70-80% EtOAc-Hexane) to afford the title compound E30 as a hygroscopic solid (257 mg, 70%). HPLC: Inertsil ODS 3V (250*4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 7.0); solvent B=CH3CN], Gradient elution program: T/% B=0/60, 10/60, 25/80, 40/80, 45/60, 50/60; 268 nm, Rt 23.93 min, 99.14% purity; MS (CI): m/z 469 (M+, 100).

With the rapid development of chemical substances, we look forward to future research findings about 1122-71-0.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishma Reddy, Velagala Venkata Rama Murali; Sesila Sridevi, Bhatlapenumarthy; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209882; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 722549-98-6, 4-Morpholinopyridin-2-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, name: 4-Morpholinopyridin-2-amine, blongs to pyridine-derivatives compound. name: 4-Morpholinopyridin-2-amine

General procedure: A solution of 2-bromo-1-(5-bromo-2,4-dimethoxyphenyl)ethanone 7 (124 rng, 0.367 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 8 (60 mg, 0.367 mmol) in acetone (4 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration and solid was washed with acetone. The solid was suspended in aqueous ammonia solution (10 ml.) and stirred for 2 h. The free base was collected by filtration and solid was washed with water, dried under reduced pressure to yield 2-(5-bromo-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 9a (51 mg, 35%) as an off-white solid. 1H NMR (300 MHz, CDCl3): delta 8.55 (s, 1H), 7.83 (d, J = 7.4 Hz, 1H), 7,80 (s, 1H), 6.55 (s, 1H), 6,43 (d, J = 2.2 Hz, 1H), 6.33 (dd, J = 2,2, 7,4 Hz, 1H), 3 ,99 (s, 3H), 3 ,94 (s, 3H), 3.40-3,30 (m, 4H), 2.10-2.00 (m, 4H); HPLC (Method 2) >99% (AUC), tR= 19.12 min: APCI MS m/z 404 [M + H]+.

The synthetic route of 722549-98-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 862695-75-8, 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. 862695-75-8, name is 6-Chloro-2-cyclopropylnicotinic acid. A new synthetic method of this compound is introduced below.

Description 14: 6-Chloro-2-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide; To a solution of 6-chloro-2-cyclopropyl-nicotinic acid (Description 13) (2. 1g) in dimethylformamide (20ml) was added 1-hydroxybenzotriazole (730mg), 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride (2. 31 g), N-ethyl morpholine (3. 2ml) followed by (tetrahydro-pyran-4-yl) -methylamine (1.9g). The mixture was stirred at room temperature overnight. Water (100ml) was added and the mixture was extracted with ethyl acetate (2x 100ml). The combined organic layers were washed with 10% sodium hydrogen carbonate (100ml), and brine (50ml). The dried (Na2SO4) organic layer was evaporated under reduced pressure. The residue was purified by Biotage chromatography over silica using ethyl acetate (60%) /isohexane (40%) to give the title compound (2. 81g) as a white solid. NMR (MeOD) b 0.96-1. 10 (4H, m), 1.28-1. 41 (2H, m), 1.65-1. 73 (2H, m), 1.80-1. 94 (1H, m), 2.24-2. 33 (1H, m), 3.24-3. 29 (2H, m), 3.37-3. 47 (2H, m), 3. 92-4.00 (2H, m), 7.16 (1H, d), 7.6 2 (1H, d). LC/MS t= 2. 39 min, molecular ion observed [MH] = 295 consistent with molecular formula C15H19ClN2O2

At the same time, in my other blogs, there are other synthetic methods of this type of compound,862695-75-8, 6-Chloro-2-cyclopropylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/75464; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 866546-07-8, name is 5-Chloro-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Chloro-1H-pyrrolo[2,3-b]pyridine

[0678] To a stirred solution of 5-chloro-1H-pyrrolo [2, 3-bj pyridine (25 g, 164 mmol) in DMSO (125 mL) at 0 C under an argon atmosphere were added potassium hydroxide (14 g, 246 mmol) and methyl iodide (35 g, 246 mmol). The reaction mixture was warmed to room temperature and stirred for 16 h. After consumption of starting material (by TLC), the reaction mixture was diluted with ice cold water (500 mL) and extracted with EtOAc (2 x 200 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain crude. The crude material was purified by column chromatography using 10% EtOAc: Hexane to afford 5-chloro-1-methyl-1H-pyrrolo [2, 3-bj pyridine (22.5 g, 83%) as a pale yellow solid. ?H NMR (CDC13, 500 MHz): 8.28 (s, 1H), 7.88 (s, 1H), 7.22 (s, 1H), 6.41 (s, 1H), 3.89 (s, 3H); LCMS: 90.6%; 166.8 (M+1); (column; Kinetex EVO C-18 (50 x 3.0 mm, 2.6 tm); RT 2.70 mm; mobile phase: 2.5mM NH400CH in water+5% ACN: ACN+5% 2.5mM NH400CH in water; T/B%: 0.01/5, 4/95, 5.5/95; flow rate: 0.8 mL/min) (Gradient); TLC: 20% EtOAc/ Hexane (Rj: 0.6).

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, 866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); 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.1594-57-6, name is N-Hydroxyisonicotinimidamide, molecular formula is C6H7N3O, molecular weight is 137.14, as common compound, the synthetic route is as follows.COA of Formula: C6H7N3O

Preparation 3: trans-4- (3-Pyridin-4-yl- [1, 2,4] oxadiazol-5-yl) cyclohexanecarboxylic acid methyl ester A solution of cyclohexane-1, 4-dicarboxylic acid monomethyl ester (1.053g, 5.66mmol) and triethylamine (800gel, 5. 66mmol) in toluene (30ml) was cooled to 0C and isobutylchloroformate (735} il, 5. 66mmol) introduced dropwise. The mixture was stirred at rt for 30min whereupon activated, powdered 3A molecular sieves (5g) and N- hydroxyisonicotinamidine (705mg, 5.14mmol) were added. The mixture was heated under reflux for 18h, cooled and filtered through celite. The solvent was removed in vacuo and the residue purified by flash chromatography (IH-EtOAc, 1: 1) to afford the title compound: RT = 3. 20min ; m/z (ES) = 288. 2 [M+H] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1594-57-6, N-Hydroxyisonicotinimidamide, and friends who are interested can also refer to it.

Reference:
Patent; PROSIDION LIMITED; WO2005/61489; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 885500-55-0, Adding some certain compound to certain chemical reactions, such as: 885500-55-0, name is Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate,molecular formula is C10H9ClN2O2, 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 885500-55-0.

Preparation Example 5; To ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (2.00 g) was added DMF (20 ml), and the mixture was ice-cooled. Sodium hydride (60% dispersed in mineral oil) (427 mg) was added thereto, followed by stirring for 1 hour under ice-cooling. Thereafter, [2-(chloromethoxy)ethyl](trimethyl)silane (1.71 mL) was added dropwise thereto, followed by warming to room temperature and stirring for 30 minutes. After completion of the reaction, to the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with EtOAc and washed with brine. The organic layer was dried over Na2SO4 and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/Hx =0/100 to 10/90) to obtain ethyl 4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (2.50 g) as a colorless transparent oily material.

According to the analysis of related databases, 885500-55-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; EP2420502; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 10592-27-5 ,Some common heterocyclic compound, 10592-27-5, molecular formula is C7H8N2, 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 0 C. solution of 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (24.0 g, 200 mmol) in N,N-dimethylformamide (68 mL) was added a 60% dispersion of sodium hydride in mineral oil (12.0 g, 300 mmol) portionwise. The mixture was stirred at 0 C. for 30 min and then a solution of tert-butyldimethylsilyl chloride (46 g, 300 mmol) in N,N-dimethylformamide (100 mL) was added to the above mixture dropwise at 0 C. The mixture was stirred at 0 C. for 3 h and then extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The yellowish residue was purified by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 5% ethyl acetate/hexanes) to afford 1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (31 g, 66%) as a yellow oil: LC/MS m/e calcd for C13H23N2Si [M+H]+ 235.42, observed 235.3; 1H NMR (400 MHz, CDCl3) delta ppm 0.35 (s, 6H), 0.98 (s, 9H, 3×CH3), 3.02 (t, J=8.6 Hz, 2H), 3.68 (t, J=8.6 Hz, 2H), 6.40 (dd, J=5.2 Hz, 7.0 Hz, 1H), 7.15 (d, J=7.0 Hz, 1H), 7.80 (d, J=5.2 Hz, 1H).

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. 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berthel, Steven Joseph; Chen, Li; Corbett, Wendy Lea; Feng, LiChun; Haynes, Nancy-Ellen; Kester, Robert Francis; So, Sung-Sau; Tilley, Jefferson Wright; US2011/144105; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem