Day: September 23, 2021

Adding a certain compound to certain chemical reactions, such as: 775288-71-6, 1-(6-Nitropyridin-3-yl)piperazine, 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: 1-(6-Nitropyridin-3-yl)piperazine, blongs to pyridine-derivatives compound. name: 1-(6-Nitropyridin-3-yl)piperazine

General procedure: A mixture of compounds 8c-8e (26.0 mmol) in acetic acid(10 mL) and methyl alcohol (40 mL) was refluxed, iron (78.0 mmol)was added. The reaction mixture was heated at 60 C for 2 h. Thereaction mixture was poured into saturated aqueous sodium carbonate(100 mL) and extracted with ethyl acetate (3 x 50 mL), thendried over sodium sulfate, filtered and concentrated. The crudeproduct was purified via column chromatography to afford compounds9c-9e.4.1.11.1. 5-(piperazin-1-yl)pyridin-2-amine (9c). White solid. Yield:68%; 1H NMR (DMSO-d6, 400 MHz) delta: 7.62 (d, J = 2.7 Hz, 1H, Pyr-H),7.17 (dd, J = 8.9, 3.0 Hz, 1H, Pyr-H), 6.40 (d, J = 8.8 Hz, 1H, Pyr-H),5.44 (s, 2H, -NH2), 3.43 (t, J = 4.0 Hz, 4H, Pyr-NCH2CH2N), 2.85 (t,J = 4.0 Hz, 4H, Pyr-NCH2CH2N). 13C NMR (DMSO-d6, 100 MHz):delta 163.0, 162.6, 149.4, 146.9, 133.7, 122.1, 120.3, 43.4, 42.6; HRMS(ESI): calcd for C9H14N4O, [(M+H)+], 179.1297, found 179.1285.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,775288-71-6, 1-(6-Nitropyridin-3-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Article; Zhao, Hui; Hu, Xiaoxia; Cao, Kai; Zhang, Yue; Zhao, Kuantao; Tang, Chunlei; Feng, Bainian; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 935 – 945;,
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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

To a 4-Chloro-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluorene-7-carboxylic acid tert-butyl ester (3.08 g, 9.40 mmol, 1.05 equiv) in 40 mL of isopropyl alcohol solution was added 3-Chloro-4-(pyridin-2-ylmethoxy)phenylamine (2.10 g, 9.0 mmol, 1 equiv) at rt. 4 N HCl in dioxane (0.1 mL) was added to the reaction mixture to accelerate the reaction. The reaction mixture was heated at 80 C. for 16 h. The mixture was allowed to cool to rt then filtered and washed with IPA (50 mL). DCM (100 mL) and sat. sodium bicarbonate (100 mL) were added to the solid. The mixture was stirred at rt for 1 h before separated the layers. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield 4.50 g of crude material. The crude material was purified by flash chromatography (50% THF/DCM) to yield a light yellow (3.60 g, 6.87 mmol, 76%) as product. 1H-NMR (DMSO-d6) delta 9.32 (broad s, 1H), 8.67 (d, J=4.0 Hz, 1H), 8.40 (s, 1H), 8.27 (s, 1H), 8.05 (t, 1H), 7.79 (d, J=2.7 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.53 (t, 1H), 7.24 (d, J=8.9 Hz, 1H), 5.35 (s, 2H), 4.66 (s, 2H), 3.66 (t, 2H), 3.19 (t, 2H), 1.43 (s, 9H); LCMS RT=3.39 min, [M+H]+=524.0.

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, 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/298297; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 272-52-6 ,Some common heterocyclic compound, 272-52-6, molecular formula is C6H5N3, 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.

Into a vessel was placed a solution comprising 1.0 g of lH-pyrazolo[4,3- b]pyridine (Exp-l-gl, 8.4 mmol) in 12 mL of MeOH/H20 (1 : 1, vol). Into the solution was added dropwise a solution of Br2 ( 1.6 g, 10 mmol) in MeOH/H20 (1 : 1, 5 mL) maintaining the solution temperature at 0 C during the addition. The reaction mixture thus prepared was stirred at this temperature for 40 min. The resulting precipitate was collected by filtration and the filter cake thus obtained was neutralized with saturated Na2C03 solution. The neutralized precipitate was filtered, washed with water and dried in vacuum. The crude product thus obtained (Exp-l-g2,1.2 g, 71 %) was used for the next step directly without purification. The identity of the product was verified by proton NMR in accordance with the procedures set forth above. 1HNMR: (400 MHz, DMSO) delta 13.66 (br, 1H), 8.55 (d, 1H, J = 4.0 Hz), 8.03 (dd, 1H, J = 8.8 Hz, 1.2 Hz), 7.42-7.45 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,272-52-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; JONES, Philip; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/63100; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 139022-27-8, 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 139022-27-8 as follows.

Example 166-fluoro-3-iodo-imidazo^ ,2-alpha]pydine (29)As shown in Fig. 5, 6-Fluoro-3-iodo-imidazo[1 ,2-alpha]pyridine (29) was prepared according to a literature procedure (Enguehard et al., J. Org. Chem. 65: 6572-6575 (2000), incorporated herein by reference in its entirety). N-iodosuccinimide (9.2g, 40.8 mmol) was added to a solution of 6-fluoro-imidazo[1 ,2-alpha]pyridine 26 (Example 15) (7.6g, 40.8 mmol) in dry acetonitrile (100 ml.) at O0C. The reaction was warmed to room temperature and then stirred for 12 hours. The mixture was filtered and the cake washed with acetonitrile and water and dried under high vacuum to afford 6-fluoro-3-iodo-imidazo[1 ,2-alpha]pyridine 29 off white solid. 8.5 g, 88% yield.1H NMR (300 MHz, CDCI3, 297K) delta 7.14 (td, J = 2.1 , 7.8 Hz, 1 H), 7.59 (dd, J = 5.1 , 9.9 Hz, 1 H), 7.72 (s, 1 H), 8.07 (distorted t, J = 3.0 Hz, 1 H).ESI MS (MeOH) calcd for C7H4FIN2 262.03, found m/z (M++1 ) 263.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,139022-27-8, its application will become more common.

Reference:
Patent; ISIS INNOVATION LTD.; EBETINO, Frank, Hallock; MAZUR, Adam; LUNDY, Mark, Walden; RUSSELL, Robert, Graham Goodwin; WO2010/33978; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1289093-31-7, 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 1289093-31-7 as follows.

Preparation 14: methyl 1 -i5-chloro-6-isobutoxypyridin-3-yl)-3-cvclopropyl-1 H- indazole-5-carboxylate; A mixture of methyl 3-cyclopropyl-1 H-indazole-5-carboxylate [preparation 9] (100mg, 0.396mmol), Cul (7.6mg, 0.40mmol), K3P04 (168mg, 0.792mmol), and 5-bromo-3- chloro-2-isobutoxy-pyridine [preparation 30] (105mg, 0.396mmol) was added to a septum sealed reaction vial and degassed. A solution of trans-N, N’- dimethylcyclohexane-1 ,2-diamine in toluene (2ml) was added. The mixture was degassed and filled with nitrogen three times, then stirred at 1 10C for 4 days. The mixture was allowed to cool and then partitioned between water (5ml) and DCM (5ml). The DCM phase was separated and the aqueous extracted with further DCM (5ml). The extracts were combined and evaporated onto silica. Purification by column chromatography (ISCO Companion, silica 12g, eluted with a gradient of heptane to 40% EtOAc in heptane) gave the title compound as clear oil (100.4mg).1 H NMR (400 MHz, CDCI3) delta ppm 1 .07 (d, 6H), 1 .19-1 .12 (m, 4H), 2.18 (septuplet, 1 H), 2.27-2.34 (m, 1 H), 3.97 (s, 3H), 4.21 (d, 2H), 7.55 (dd, 1 H), 7.98 (d, 1 H), 8.09 (dd, 1 H), 8.35 (d, 1 H), 8.58 (dd, 1 H).LCMS (Method A5) Rt 1 .83 min, MS m/z 400 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1289093-31-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; BELL, Andrew Simon; DE GROOT, Marcel John; LEWTHWAITE, Russell Andrew; MARSH, Ian Roger; SCIAMMETTA, Nunzio; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/95781; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 78607-36-0 ,Some common heterocyclic compound, 78607-36-0, molecular formula is C5H3ClIN, 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.

EXAMPLE 31K 3-(4-tert-butylphenyl)-1-({2-[(2-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione To a solution of 0.8 g of 1-[(2-aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione hydrochloride obtained in stage c) of Example 7 in 50 mL of dioxane are successively added under argon 0.628 g of 2-chloro-3-iodopyridine, 2.8 g of caesium carbonate, 150 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) (xantphos) and 49 mg of palladium diacetate. The reaction mixture is heated at 90 C. for 3 hours and then filtered, and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluding with a mixture of cyclohexane and ethyl acetate (70/30 by volume) to give 0.51 g of 3-(4-tert-butylphenyl)-1-({2-[(2-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows: 1H NMR spectrum at 400 MHz: 1.31 (s, 9H); 1.43 (s, 6H); 4.57 (s, 2H); 6.89 (dd, J=1.5 and 5.5 Hz, 1H); 7.11 (broad s, 1H); 7.39 (m, 3H); 7.52 (d, J=8.5 Hz, 2H); 8.00 (dd, J=2.0 and 5.0 Hz, 1H); 8.10 (d, J=5.5 Hz, 1H); 8.55 (m, 2H). Mass Spectrum (ES): m/z=478 [M+H]+; m/z=476 [M-H]-

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. 78607-36-0, 2-Chloro-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2009/82379; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 110860-92-9, 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. 110860-92-9, name is 5,6-Dichloropyridin-3-ol. A new synthetic method of this compound is introduced below.

Sodium acetate (4.Og, 49.38mmoI) was added to a mixture of 5,6-dichloropyridin-3-ol (8g, 49.38mmol), Pd(OAc)2 (1.43g, 6.41 mmol) and Pd(dppf)C12 DCM complex (5.23g, 6.4lmmol) in EtOH (lOOmL) in an autoclave. The autoclave was filled with CO gas (22Opsi) and stirred at 90C for 6 h. The reaction mass was cooled to RT, excess gas evacuated in vacuo and the reaction mass was filtered through a celite bed. It was washed with EtOAc and the clear filtrate was concentrated under reduced pressure. Theresidue was purified by CC (0-40% EtOAc in PE) and the pure fractions were concentrated to get ethyl 3- chloro-5-hydroxypicolinate (9.2g, 93%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,110860-92-9, 5,6-Dichloropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); 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.153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Chloro-4-iodopyridine

Intermediate 1; 4-Iodo-1H-pyridin-2-one; To 10.0 g (41.8 mmol) 2-chloro-4-iodopyridine in 100 mL AcOH are added 17.1 g (208 mmol) NaOAc and the reaction mixture is heated at 180 C. for 2 h in a microwave oven. DCM and water are added to the reaction mixture and the layers are separated. The organic layer is washed with water, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is triturated with TBME.C5H4INO (M=221.0 g/mol),ESI-MS: 222 [M+H]+ Rf (TLC): 0.3 (silica gel DCM/MeOH 9/1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

b) 4-(Benzyloxy)-1-(1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-8-yl)pyridin-2(1H)-one hydrochloride A suspension of 4-(benzyloxy)pyridin-2(1H)-one (71 mg, 0.35 mmol), tert-butyl 8-bromo-6-tosyl-1,2,4,5-tetrahydroazepino[4,5-b]indole-3(6H)-carboxylate (202 mg, 0.389 mmol), CuI (81 mg, 0.43 mmol), 8-hydroxyquinoline (62 mg, 0.43 mmol) and Cs2CO3 (127 mg, 0.389 mmol) in DMSO (10 mL) was degassed under reduced pressure for 45 min. The suspension was put under N2 and stirred at 135 C. for 4.5 h. The suspension was cooled, 9:0.9:0.1 CH2Cl2/MeOH/NH4OH (10 mL) was added, and the resulting suspension was stirred at 25 C. for 30 min. The suspension was passed through a plug of silica gel, and the filtrate was washed with brine. The resulting solution was dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded 190 mg of a yellow solid. NaOH (594 mg, 14.8 mmol) was added to a solution of the yellow solid in 1:1 MeOH/CH2Cl2 (20 mL) under N2, and the resulting suspension was stirred at reflux for 16 h. The reaction was cooled, H2O was added, and the resulting suspension was filtered. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded a green solid. Preparative HPLC (Phenomenex Luna C18 (2), 250.0*50.0 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA) afforded 50 mg of a white powder. 2 N HCl in Et2O (200 mL) was added to a solution of the white powder in 1:1 CH2Cl2/MeOH (4 mL) under N2, and the resulting suspension was stirred at 25 C. for 18 h. The suspension was filtered, and the solid was washed with Et2O to afford the title compound (35 mg, 23%) as a white solid: mp 258-260 C.; 1H NMR (500 MHz, DMSO-d6) delta 11.18 (s, 1H), 9.06 (br s, 2H), 7.57-7.35 (m, 7H), 7.25 (s, 1H), 6.90 (d, J=8.0 Hz), 6.11-6.07 (m, 1H), 5.96 (s, 1H), 5.15 (s, 2H), 3.45-3.30 (m, 4H), 3.20-3.15 (m, 2H), 3.12-3.06 (m, 2H); ESI MS m/z 386 [M+H]+.

According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 39919-65-8, name is 2,5-Dibromo-6-methylpyridine, molecular formula is C6H5Br2N, 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. name: 2,5-Dibromo-6-methylpyridine

Add to the reaction flask3,6-dibromo-2-methylpyridine (1.0 g, 3.9 mmol)And anhydrous ether (10 mL) were cooled to -78C,N-BuLi (1.6 M in hexanes, 2.4 mL, 3.9 mmol) was added dropwise,After stirring for 1 hour, anhydrous DMF (307 mg, 4.2 mmol) was added,The reaction was stirred at room temperature for 1 hour. Saturated ammonium chloride solution (10 mL) was added,Ethyl acetate (20 mL x 3). Combine organic phase,Saturated sodium chloride solution (20mL), dried over anhydrous sodium sulfate, suction filtration,Concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / petroleum ether = 1: 10)The resulting residue was purified to give the title compound (0.4 g, white solid) in 51% yield.

With the rapid development of chemical substances, we look forward to future research findings about 39919-65-8.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem