Pyridine-derivatives

Electric Literature of 1334411-79-8, 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. 1334411-79-8, name is 4-Bromo-2-(2,6-dichlorophenyl)-1H-imidazo[4,5-c]pyridine, molecular formula is C12H6BrCl2N3, 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.

A mixture of 4-bromo-2-(2,6-dichlorophenyl)-3H-imidazo[4,5-c]pyridine (400 mg, 1.166mmol)andcyclopropanecarboxamide(198 mg, 2.33mmol), Pd2dba3(53 mg, 0.0583mmol),XantPhos(67 mg, 0.117mmol) and Cs2CO3(1.14 g, 3.5mmol) in 1,4-dioxanes (5 mL)and 1,2-dimethoxyethane (5 mL) was heated in a microwave at 150C for 10 min. The reaction mixture was cooled and filtered, and the filter cake was washed withdichloromethane. The combined organics were washed with brine, dried over MgSO4and concentrated. The crude product was purified by reverse phase HPLC to give the title compound (321 mg, 79% yield) as a white solid.1H NMR (500 MHz, DMSO-d6) delta 12.25 (s, 1H), 10.99 (s, 1H), 8.10 (d,J= 5.6 Hz, 1H), 7.63 (q,J= 6.8 Hz, 4H), 7.56 – 7.35 (m, 1H), 2.07 (s, 0H), 0.89 (d, J = 33.0 Hz, 4H). HRMS m/z [M+H]+calcd.forC16H12Cl2N4O 347.0466, found 347.0458.

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 1334411-79-8, 4-Bromo-2-(2,6-dichlorophenyl)-1H-imidazo[4,5-c]pyridine.

Reference:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
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

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

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

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

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

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

Related Products of 73583-37-6, Adding some certain compound to certain chemical reactions, such as: 73583-37-6, name is 4-Bromo-2-chloropyridine,molecular formula is C5H3BrClN, 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 73583-37-6.

(1) Tert-butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate A mixture of 4-bromo-2-chloropyridine (3.87 ml, 34.9 mmol), tert-butyl piperazine-1-carboxylate (5.0 g, 26.9 mmol), trisdibenzylideneacetone dipalladium (492 mg, 0.537 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (932 mg, 1.61 mmol), sodium tert-butoxide (3.87 g, 40.3 mmol) and toluene (270 ml) was stirred at 100 C. for 6 hours. The reaction was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate_hexane=1:1) to obtain the title compound (5.62 g, 70%) as a solid. 1H NMR (CDCl3) delta: 1.49 (9H, s), 3.30-3.37 (4H, m), 3.52-3.60 (4H, m), 6.57 (1H, dd, J=6.1, 2.4 Hz), 6.65 (1H, d, J=2.4 Hz), 8.04 (1H, d, J=6.1 Hz). (1) Tert-butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate; To a solution of 4-bromo-2-chloropyridine (15.0 g, 77.3 mmol) and tert-butyl piperazine-1-carboxylate (18.0 g, 77.3 mmol) in anhydrous toluene (400 ml) was added sodium tert-butoxide (11.0 g, 116 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (1.34 g, 2.32 mmol) and trisdibenzylideneacetone dipalladium (445 mg, 0.77 mmol) under nitrogen atmosphere, and the reaction was deaerated and heated under reflux for 14 hours. The reaction was distilled off under reduced pressure and to the residue was added ethyl acetate and water followed by extracted. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:1) to obtain the title compound (16.0 g, 70%) as a solid.1H NMR (CDCl3) delta: 1.45 (9H, s), 3.30-3.32 (4H, m), 3.52-3.54 (4H, m), 6.52-6.55 (1H, m), 6.01 (1H, s), 7.97-8.04 (1H, m).

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. 73583-37-6, 4-Bromo-2-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/163508; (2009); 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. 16665-38-6, name is (4-Methoxypyridin-2-yl)methanol. A new synthetic method of this compound is introduced below., SDS of cas: 16665-38-6

Synthesis of 2-azidomethyl-4-methoxypyridine.[0298] 2-Hydroxymethyl-4-methoxypyridine (278 mg, 2.0 mmol) was dissolved in tetrahydrofuran (15 mL) in a 50 mL round-bottomed flask under argon. The flask was cooled to 0-5 C with an ice/water bath for 10 minutes at which time, powdered OH (157 mg, 2.8 mmol) was added followed by /?erra-toluenesulfonyl chloride (pTsCl). The reaction was stirred for 12 hours, at which time diethyl ether (30 mL) was added. The mixture was transferred to a separatory funnel, and a saturated solution of NaHCC>3 (40 mL) was added. The organic layer was dried with MgSC>4, filtered, and concentrated to a residue, which was chromatographed on a silica gel column with a 10% to 50% gradient of ethyl acetate/hexanes. Rf = 0.69 (ethyl acetate, 254 nm UV). This material was then dissolved in N,N-dimethylformamide (5 mL), and sodium azide (266mg, 4.09 mmol) was added and the reaction was stirred at ambient temperature for 16 hours, at which time the reaction mixture was diluted with diethyl ether (30 mL) and washed with a saturated solution of NaHCC>3 (3 x 30 mL), then with brine (25 mL), dried with MgS04, filtered and concentrated in vacuo. The resulting residue was chromatographed over silica gel with a 15% to 50% gradient of ethyl acetate/hexanes to furnish 100 mg (30% yield) of this compound as a light yellow oil. Rf = 0.68 (ethyl acetate, 254 nm UV). NMR (400MHz, CDCh): 8.34 (d, J= 5.6 Hz, 1H,), 6.81 (d, J= 2.4 Hz 1 H), 4.39 (s, 2H), 3.81 (s,

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, 16665-38-6, (4-Methoxypyridin-2-yl)methanol.

Reference:
Patent; LIFE TECHNOLOGIES CORPORATION; GEE, Kyle; SINGH, Upinder; GRECIAN, Scott; WO2012/121973; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3510-66-5, 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. 3510-66-5, name is 2-Bromo-5-methylpyridine, molecular formula is C6H6BrN, 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.

Add 6-bromo-3-methylpyridine to methanol, reduce the temperature to 20-30 C in an ice-water bath, and slowly drop the methanol solution of sodium methoxide into the reaction system, keeping the internal temperature below 40 C. , Heated to reflux, reacted at 70-80 C for 12h, the reaction equation is as follows:The temperature of the reaction solution was reduced to 45-50 C, and concentrated to half the volume under reduced pressure; the temperature was reduced to 25-30 C, and water was added. The amount of water added was 5.5-8.0 times that of 6-bromo-3-methylpyridine, and stirred for 10min. ; The treatment solution was extracted three times with dichloromethane. The amount of dichloromethane was 10.0-12.0 times that of 6-bromo-3-methylpyridine. The organic phases were combined and washed once with water. -Methoxy-3-methylpyridine, yield 94.3%, GC purity 99.1%.Among them, the amount of methanol is 4.5-5.0 times that of 6-bromo-3-methylpyridine.The molar ratio of 6-bromo-3-methylpyridine to sodium methoxide is 1: 1.4.

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 3510-66-5, 2-Bromo-5-methylpyridine.

Reference:
Patent; Nanjing Habo Pharmaceutical Technology Co., Ltd.; Zhao Xiaolin; Cui Jiayi; Wang Jinzhu; Zhao Bing; Ai Yangbao; (10 pag.)CN110878043; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem