Pyridine-derivatives

Electric Literature of 18653-75-3, 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 18653-75-3, name is 2-(1H-Imidazol-2-yl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Na2MoO4·2H2O (0.847g, 3.5mmol), 2-pyim (0.0065g, 0.040mmol), Mo powder (0.06g, 0.60mmol), ZnCl2 (0.136g, 1mmol), H3PO3 (0.02g, 0.25mmol), tetrabutylammonium hydroxide (TBAOH, 0.2mL, 0.3mmol) and distilled water (9.0mL) were stirred for 1h under the room temperature. An aqueous solution of 2molL-1 HCl was added into the mixture and the pH value was adjusted to 3.8. After that, the mixture continues to stir for an another 2h. Finally, the product was transferred to 25 Teflon-lined antoclave and was heated to 180C for 3days before cooled down to the room temperature. In the end, dark-red crystals 2 were collected and dried in air (yield: 62.45%). Elemental analysis: calculated: C, 14.11; H, 1.36; N, 6.17; found: C, 14.01; H, 1.28; N, 6.58.

According to the analysis of related databases, 18653-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Han, Ye-Min; Cheng, Wei-Wei; Cao, Jia-Peng; Yang, Mu-Xiu; Hong, Ya-Lin; Kang, Run-Kun; Xu, Yan; Inorganica Chimica Acta; vol. 498; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 850349-02-9, 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.850349-02-9, name is 8-Bromoimidazo[1,2-a]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.

l-Iodo-2,5-pyrrolidinedione (2.28 g, 10.15 mmol) was added to a solution of 8-bromo- imidazo[l,2-a]pyridine (2 g, 10.15 mmol) in CH3CN (8 ml). The r.m. was stirred at r.t. for 30 min. The mixture was concentrated in vacuo and the residue was purified by flash chromatography over silicagel (eluent: DCM/MeOH(NH3) from 100/0 to 99/1). The product fractions were collected and the solvent was evaporated in vacuo. Yield: 2.89 g of intermediate 5 (84.6 %).

Statistics shows that 850349-02-9 is playing an increasingly important role. we look forward to future research findings about 8-Bromoimidazo[1,2-a]pyridine.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2010/70008; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 286947-03-3, 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.286947-03-3, name is 5-Bromo-2-chloro-3-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

c. Preparation of Compound To a 25 mL flask containing (63.8 mg, 1.2 mmol) of sodium ethoxide was added 3 mL dry ethanol. The mixture was stirred for 30 minutes. 2-Chloro-3-methoxy-5-bromopyridine (230 mg, 1.04 mmol) was added to the mixture and heated to 60 C for 16 hours. The reaction was allowed to cool and the solvent was removed. Ethyl acetate was added (50 ml) was added to the residue. The ethyl acetate solution was washed with water and then brine. The organic solvent was dried and concentrated, purified by ISCO flash chromatography using 10% ethyl acetate in hexane to give 220 mg (97% yield) of the desired product. NMR (300 MHz, CDC13) delta: 7.71 (s, IH), 7.09 (s, IH), 4.37 (qt, 2H), 3.82 (s, 3H), 1.38 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 286947-03-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LAVOIE, Edmond J.; BAUMAN, Joseph David; PARHI, Ajit; SAGONG, Hye Yeon; PATEL, Disha; ARNOLD, Eddy; DAS, Kalyan; VIJAYAN, Suyambu Kesava; WO2014/43252; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1072-97-5, 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 1072-97-5 as follows.

Step-1: Synthesis of ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate To a stirred solution of 5-bromopyridin-2-amine (10.0 g, 56.0 mmol, 1.0 eq.) and ethyl 3-bromo-2-oxopropanoate (12.6 g, 64.0 mmol, 1.1 eq.) in Dioxane (200 mL) was added MgSO4 (20.0 g, 150.0 mmol, 3.0 eq.) at RT. The resulting mixture heated to 80 C. for 16 h. Following this, reaction mixture cooled to RT filtered the solid and under vacuum and filtrate concentrated to get crude. The crude purified by normal phase silica-gel column to get title compound (12 g, 79%). LCMS: 269.9 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 8.91 (d, J=1.32 Hz, 1H) 8.47 (s, 1H) 7.62 (d, J=9.65 Hz, 1H) 7.47 (dd, J=9.65, 1.75 Hz, 1H) 4.31 (q, J=7.16 Hz, 2H) 1.31 (t, J=7.02 Hz, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1072-97-5, its application will become more common.

Reference:
Patent; INTEGRAL BIOSCIENCES PRIVATE LIMITED; CHAKRAVARTY, Sarvajit; PENDHARKAR, Dhananjay; RAMACHANDRAN, Sreekanth A.; BATHULA, Chandramohan; SONI, Sanjeev; KUMAR, Vivek; SAEED, Uzma; DANODIA, Abhinandan Kumar; SHARMA, Ankesh; JADHAVAR, Pradeep S.; US2020/206233; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1603-40-3, 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 1603-40-3, name is 3-Methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1; Synthesis of 3-amino-1-hydroxy-3,4-dihydro-1,8-naphthyridin-2(1H)-one, trifluoroacetate salt (8); 3-Methyl-2-nitropyridine (2); To a solution of H2O2 (120 g, 1.1 mol) in fuming sulfuric acid (250 mL) was added a solution of 3-methylpyridin-2-amine (1) (16 g, 0.15 mol) in concentrated sulfuric acid (50 mL) drop-wise, while keeping the reaction temperature at 0 C. After stirring for 3 h at 10-25 C., the reaction mixture was brought to pH=11-12 by adding an aqueous 40% NaOH solution at 0-5 C. The resulting mixture was extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over Na2SO4 and filtered. The solvent was removed in vacuo to give the desired compound (18.2 g, 89%) as a yellow oil.

According to the analysis of related databases, 1603-40-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2010/324043; (2010); 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. 136117-74-3, name is Imidazo[1,2-a]pyridine-8-carbaldehyde, the common compound, a new synthetic route is introduced below. COA of Formula: C8H6N2O

Preparation of ethyl imidazopyridine propenoate (According to the Literature Method: Chezal, J. M. and al. J. Org. Chem. 2001, 66, 6576-6584).Ethyl azidoacetate (1.81 g, 14.0 mmol) was added dropwise at -30 C. to a stirred solution containing sodium (0.20 g, 8.70 mmol) in dry ethanol (10 mL). To this solution was added dropwise a solution of aldehyde 4 (1.00 mmol) in dry ethanol (8 mL). The reaction mixture was returned back room temperature and stirred for 3 h (CAUTION: an exothermic reaction can take place, with gas expansion). The solution was poured into aqueous saturated ammonium chloride solution (30 mL) and then extracted with CH2Cl2. The organic layers were dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by chromatography using CH2Cl2 as eluent to afford the azide derivative 6; Example 35 Ethyl alpha-azido-beta-(imidazo[1,2-a]pyridin-8-yl)propenoate (6a) From 4a (yield: 10%); mp: 150-152 C.; IR (KBr) 2100, 1700, 1600, 1280 cm-1; 1H NMR (400 MHz, CDCl3) delta 1.41 (t, 3H, J=7 Hz), 4.39 (q, 2H, J=7 Hz), 6.83 (t, 1H, J=7 Hz), 7.57 (d, 1H, J=1 Hz), 7.61 (d, 1H, J=1 Hz), 7.76 (s, 1H), 8.06 (dd, 1H, J=7, 1 Hz), 8.17 (dd, 1H, J=7, 1 Hz). MS m/z 257 (M+, 1), 229 (61), 183 (100), 155 (31), 129 (23), 104 (14). Further elution gave 8-methylimidazo[1,2-a]pyridine (yield: 10%-Kaiser, C. and al. J. Med. Chem. 1992, 35, 4415-4424).

The synthetic route of 136117-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universite D’Auvergne Clermont 1; Universite Francois Rabelais Tours; Katholieke Universiteit Leuven; US2010/93781; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59281-14-0, 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one, 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, Computed Properties of C13H13NO3, blongs to pyridine-derivatives compound. Computed Properties of C13H13NO3

To a stirred solution of compound 9b (2.7g) in NaOH solution (0.567g in 55 mL of water) was added 10%Pd-C(l .4g) portion wise under nitrogen atmosphere. The nitrogen was replaced with hydrogen and stirred at RT for 16h. The reaction mass was filtered under celite and concentrated under reduced pressure to give 2.2 g of the required compound as a mixture. Proceeded with crude to the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59281-14-0, 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; VITAS PHARMA RESEARCH PVT LTD; ALAPATI, Chandrasekhar; BANERJEE, Ankita; RANGARAJAN, Radha; KUMAR, Rajinder; WO2014/57415; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55676-22-7, 3-Acetyl-6-chloropyridine, 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, Safety of 3-Acetyl-6-chloropyridine, blongs to pyridine-derivatives compound. Safety of 3-Acetyl-6-chloropyridine

To a solution of l-(6-chloropyridin-3-yl)ethanone (4.0 gm, 0.0257 mole) in DMF (15 mL), cesium carbonate (16.8 gm, 0.051 mole) was added followed by addition of methyl 2-hydroxyacetate (8.0 ml, 0.103 mmoles) at 25 C under nitrogen atmosphere and the reaction mixture was stirred at 80-90 C for 18 h. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure. The crude product was purified by colunm chromatography (Eluent: 16% ethyl acetate in hexane) to yield 1.25 gm (23%) of product as off white solid. NMR: DMSO-< 6,? 2.55 (s, 3H), 3.67 (s, 3H), 5.02 (s, 2H), 7.04 (dd, J = 8.8 & 0.4 Hz, 1H), 8.20 (dd, J= 8.8 & 2.4 Hz, 1H), 8.78 (d, J= 2.0 Hz, 1H). At the same time, in my other blogs, there are other synthetic methods of this type of compound,55676-22-7, 3-Acetyl-6-chloropyridine, and friends who are interested can also refer to it. Reference:
Patent; CADILA HEALTHCARE LIMITED; DESAI, Ranjit, C.; PINGALI, Harikishor; PANDYA, Vrajesh; MAKADIA, Pankaj; PATEL, Pankaj; WO2014/192023; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 778611-64-6, 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. 778611-64-6, name is 5-Bromo-2-chloro-4-methylpyridine, molecular formula is C6H5BrClN, 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.

Step 1 : To a solution of BB-3 (100 mg, 0.287 mmol) in toluene (10 mL), K2C03 (119 mg, 0.86 mmol), 5- bromo-2-chloro-4-methylpyridine (77 mg, 0.373 mmol) and Lambda/,/V -dimethyl ethylene diamine (13 mg, 0.143 mmol) were added and the mixture was degassed through purging with Ar for 30 min. Cul (27 mg, 0.14 mmol) was added and the RM was heated to 100C for 48 h. The RM was chilled, diluted with toluene and filtered over a plug of celite. The volatiles were removed under reduced pressure and the residue was purified by flash CC (silica gel, Hex/EtOAc) to yield the desired compound (60 mg, 45%).

According to the analysis of related databases, 778611-64-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, Felix; RITTER, Stefanie; NORDHOFF, Sonja; WACHTEN, Sebastian; OBERBOeRSCH, Stefan; KLESS, Achim; WO2015/22073; (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.119285-07-3, name is tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, molecular weight is 278.3501, as common compound, the synthetic route is as follows.name: tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

To a stirring solution OF CYCLOPENTYL- (4, 6-DICHLORO- [1, 3,5] triazin-2-yl) – amine (0.60g, 2.57 mmol) prepared as in Example 14A above in 5 ML OF acetonitrile was added 4- (5-AMINO-PYRIDIN-2-YL PIPERAZINE-1-CARBOXYLIC acid tert- butyl ester (0.72g, 2.6 mmol) and triethylamine (0.36 mL, 2.6 mmol). The mixture was stirred at ambient temperature. After 20 minutes, solids formed. The solids were filtered off and washed several times with acetonitrile. The solids were dried in a vacuum oven for 1.5 hours at 60C. Purification was accomplished via silica column chromotography in 7: 1 dichloromethane/acetone. The desired fractions were collected and concentrated in vacuo to afford N- Cyclopentyl-N’, N”-BIS- (6-PIPERAZIN-1-YL-PYRIDIN-3-YL)-1, 3,5-triazine-2, 4,6- triamine (Compound B) as a brown foam/solid (0.234g, 19%). Ms 517.3 ; Mp >290.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,119285-07-3, tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/65378; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem