Category: pyridine-derivatives

Electric Literature of 13534-98-0, 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. 13534-98-0, name is 4-Amino-3-bromopyridine. A new synthetic method of this compound is introduced below.

General procedure: A mixture of amino pyridine 1 (1.0 mmol), 10%Pd/C (0.010 mmol), CuI (0.010 mmol), PPh3 (0.022 mmol) and Cs2CO3 (3 mmol) in PEG-400 (3 mL) was stirred for 15 min at room temperature under a nitrogen atmosphere. To this was added an appropriate iodoarene 2 (1.0 mmol) and the mixture was stirred further for 10 min. The mixture was then stirred at 95 – 100 C for 2.5 h under ultrasound irradiation using a laboratory ultrasonic bath Sonorex Super RK 510H model producing irradiation of 35 kHz. After cooling the mixture to room temperature an appropriate terminal alkyne 3 (1.2 mmol) was added to it. The mixture was then stirred again at 95-100 C for 4h under ultrasound irradiation. After completion of the reaction (indicated by TLC), the mixture was diluted with cold water (30 mL) and extracted with CH2Cl2 (3 x 10 mL). The organic layers were collected, combined, washed with cold water (2 x 15 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography on silica gel using EtOAc / n-hexane as a solvent system.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-98-0, 4-Amino-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Article; Dandela, Rambabu; Nath Singh, Shambhu; Pal, Manojit; Ramamohan, Hindupur; Siddaiah, Vidavalur; Venkateshwarlu, Rapolu; Tetrahedron Letters; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 73870-24-3 ,Some common heterocyclic compound, 73870-24-3, molecular formula is C6H7Br2N, 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.

Cytosine-pyridine (2) was obtained by mixing cytosine (0.65 g,5.93 mmol, 3 eq) and KI (10 mg, catalytic amount) in 10 mL of dry DMF. After degassing the suspension with argon for 15 min, NaH(0.118 g, 4.9 mmol, 2.5 eq) was added and the mixture was stirredfor 30 min. A solution of 4-(bromomethyl)pyridine hydrobromide(0.5 g, 1.97 mmol, 1 eq) in 4 mL of dry DMF was slowly added to themixture. The mixture was stirred at 40C overnight and the reac-tion progress was followed by TLC. The crude was dried undervacuum and then washed with a minimum amount of water. Theproduct was puried by column chromatography (silica gel, MeOH:Et3N: DCM 1:0.2:20) affording compound 2 (120 mg, 30%) as awhite powder; dH (500 MHz, DMSO-d6) 4.87 (2H, s, Ha), 5.73 (1H, d,3J 7.2 Hz, Hb), 7.08 (1H, s, brd, NH), 7.17 (2H, d,3J 6.0 Hz, Hm),7.21 (1H, s, brd, NH), 7.69 (1H, d,3J 7.2 Hz, Hc), 8.50 (2H, d,3J 6.0 Hz, Ho); dC (126 MHz, DMSO-d6) 50.6 (Ca), 93.9 (Cb), 122.0(Cm), 146.1 (Cc), 147.0 (Cp), 149.7 (Co), 155.7 (Cd), 166.1 (Ce); HRMS(ESI): MH, found 203.0934. C10H10N4O requires 203.0927; IR(cm1): 3337.24, 3115.39, 1652.03, 1597.71, 1486.09, 1423.17,1384.39, 1369.72, 1278.91, 1208.06, 1130.29, 965.29, 815.97, 781.56,704.43, 682.80, 567.57, 521.43, 474.65, 405.44.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73870-24-3, its application will become more common.

Reference:
Article; Bulach, Veronique; Hosseini, Mir Wais; Jouaiti, Abdelaziz; Kyritsakas, Nathalie; Tufenkjian, Elsa; Tetrahedron; vol. 76; 9; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14432-12-3, 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.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 4-amino-2-chloropyridine (1.28 gm, 10 mmol) and di-tert-butyl dicarbonate (2.21 gm, 10.1 mmol) in THF (20 mL) was cooled to 00C and a solution of IM lithium bis(trimethylsilyl)amide in THF ( 20 mL, 20 mmol) was added slowly maintaining the temperature below 00C. The reaction was allowed to warm to room temperature over one hour and then quenched by the addition of 1.5 N aqueous ammonium chloride (15 mL). After stirring for several hours the reaction was extracted into ethyl acetate, washed with brine, the organic layer dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether give pure tert-butyl (2-chloropyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 25 – 45% ethyl acetate/ hexane to afford more product. EPO A solution of tert-butyl (2-chloropyridin-4-yl)carbamate (1.14 gm, 5 mmol) in dry THF (20 mL) was cooled to -700C under an inert atmosphere and 1.7 M t-butyl lithium/pentane (8 mL, 13.5 mmol) was slowly added. The reaction was stirred for two hours and then dry DMF (1.2 mL, 15.5 mmol) was added. The reaction was allowed to slowly warm to room temperature over a three hour period. The reaction mixture was quenched with 3 N HCl (12 mL) and diluted with diethyl ether. The ether layer was washed with aqueous NaHCtheta3, dried (over Na2SO4), filtered and evaporated. The residue was triturated with cold diethyl ether to give pure t-butyl (2-chloro-3-formylrhoyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 15-20% ethyl acetate/hexane to give additional product. 1H-NMR(5OO MHz, CDCI3): deltall.O (IH, br s), 10.52 (IH, s), 8.38 (IH, d, J= 6 Hz), 8.31 (IH, d, J= 6 Hz), 1.54 (9H, s); m/e (m+1): 257.2.

The chemical industry reduces the impact on the environment during synthesis 14432-12-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 4487-57-4, 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 4487-57-4, name is 2,4-Dibromo-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-Bromo-5-nitropyridin-4-amine (Compound 63) To a solution of 2,4-dibromo-5-nitropyridine (200 mg, 0.709 mmol) and triethylamine (0.2 ml, 1.419 mmol) in THF 7 M ammonia (0.2 ml, 1.419 mmol) was added and stirred at room temperature for 24 h. Solvents were removed and the crude was purified by combiflash SiO2 chromatography (0-50% EtOAc-hexanes) to give 2-bromo-5-nitropyridin-4-amine (135 mg, 87%) as a tan solid. 1H-NMR (400 MHz, CD3OD) delta ppm 8.82 (s, 1H), 7.11 (s, 1H); m/z 219.69 (M+H)+.

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 4487-57-4, 2,4-Dibromo-5-nitropyridine.

Reference:
Patent; Stingray Therapeutics, Inc.; The University of Utah; Vankayalapati, Hariprasad; Liu, Xiaohui; Ramamoorthy, Gurusankar; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (59 pag.)US2019/31655; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 918516-27-5, 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. 918516-27-5, name is 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C13H9ClN2, 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.

AICI3 (1.18 g, 8.87 mmol) was added to DCM (40 mL) and the mixture was stirred for 10 min at RT followed by cooling to 0C. 5-(4-chlorophenyl)-1 H-pyrrolo[2,3-b]pyridine (2) (1 eq., 405.92 mg, 1.77 mmol) was added and the mixture was stirred for 30 min then warmed to RT for 3 h. solution A was slowly added to the above suspension at 0 C and the reaction was stirred for 2 days at RT. After complete conversion, the reaction was quenched with methanol (MeOH, 10 mL) and concentrated to give a dark brown residue. Cold water (50 mL) was added to the residue and the pH of the solution was adjusted to 7 (neutral) with aq. ammonia. EtOAc (50 mL) was added and the mixture was stirred for 30 min. It was then filtered through celite, the filtrate was extracted with EtOAc (20 mL x 3) and the combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to get crude N-(2,4-dibromo-3-(5-(4-chlorophenyl)-1 H-pyrrolo[2,3- b]pyridine-3-carbonyl)-phenyl)propane-1 -sulfonamide (900 mg, crude) which was used in the next step without further purification.

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 918516-27-5, 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; HEPAREGENIX GMBH; ALBRECHT, Wolfgang; LAUFER, Stefan; SELIG, Roland; KLOeVEKORN, Phillip; PRAeFKE, Bent; (187 pag.)WO2020/16243; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 866546-07-8, 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. 866546-07-8, name is 5-Chloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5ClN2, 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 solution of bromine (3.5mol) in chloroform (40mol) was added dropwise to an ice-cold solution of the 5-chloro-1H- pyrrolo[2,3-b]pyridine (3) (10g, 65mM) in chloroform (260mol). The reaction mixture was stirred for 60 minutes at 0C. The reaction mixture was then hydrolyse with water and the pH of the solution was adjusted to 10. The resulting solid was removed by filtration, and the. aqueous was extracted with dichloromethane. The organic was washed with water, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (10.5g, 69%). 1H NMR (DMSO-d6) 7.8 (1H, s), 7.9 (1H, s), 8.3 (1H, s)

According to the analysis of related databases, 866546-07-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED?; WO2005/95400; (2005); 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. 874302-76-8, name is 4-nitrophenyl 2-(pyridin-2-yldisulfanyl)ethyl carbonate. A new synthetic method of this compound is introduced below., Quality Control of 4-nitrophenyl 2-(pyridin-2-yldisulfanyl)ethyl carbonate

To a solution of compound 3 (230.52 mg, 654.17 umol) in DMF (2 mL) was added Motohmod (0.15 g, 327.09 umol), DIEA (126.82 mg, 981.26 umol, 170.92 uL) and HOBt (53.04 mg, 392.50 umol). The mixture was stirred at 25 C for 16 hr. LC-MS indicated compound 3 was consumed completely and a peak with desired mass (m/z: 672.1([M+H+])) was detected. The reaction mixture was purified by prep-HPLC (A: H20, B: ACN). Compound 4 (0.11 g, 163.72 umol, 50.05% yield) was obtained as a white solid. Calculated MW: 671.8 observed m/z: 672.1([M+H+])

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, 874302-76-8, 4-nitrophenyl 2-(pyridin-2-yldisulfanyl)ethyl carbonate.

Reference:
Patent; BICYCLERD LIMITED; KEEN, Nick; MCDONNELL, Kevin; PARK, Peter U.; MUDD, Gemma Elizabeth; IVANOVA-BERNDT, Gabriela; (274 pag.)WO2019/34868; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 115170-40-6, 5-Bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine, 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, Recommanded Product: 115170-40-6, blongs to pyridine-derivatives compound. Recommanded Product: 115170-40-6

Intermediate IV andBromo-2,3-dihydro-1H-pyrrolo (2,3-b) pyridine to give d,React with (S) -3-hydroxytetrahydrofuran,A dark yellow solid VId was obtained.The intermediate d with activated carbon,Ferric chloride and hydrazine hydrate reduction,Obtained as an off-white solid VIId.Then VIId and diethyl phosphoric acid condensation,Compound VIIId is obtained,In the condensation with (dimethylamino) acetaldehyde diethyl acetal,The target compound was obtained. Yield: 48.7%.

The synthetic route of 115170-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Ouyang Yiqiang; Tang Qidong; Xu Shan; Tu Yuanbiao; Duan Yongli; Lei Huajun; Wang Caolin; (23 pag.)CN106831725; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60032-57-7 ,Some common heterocyclic compound, 60032-57-7, molecular formula is C7H7NO, 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.

General procedure: 4-Chlorophenylmagnesium bromide (1.0 M in Et2O; 11.0 mL, 11.0 mmol) was added dropwise to a stirred solution of 2-chloronicotinaldehyde 2b (1.42 g, 10.0 mmol) in dry THF (50 mL) under a nitrogen atmosphere at ambient temperature. After 30 minutes, the reaction was quenched by the addition of saturated ammonium chloride (aq; 100 mL). The product was extracted with EtOAc (2 × 100 mL) and the extracts washed with brine (100 mL), combined and dried (MgSO4). The crude product was recrystallised from hot 5% EtOAc-hexane to give the alcohol 5a (1.99 g, 78%) as a white crystalline solid, mp 102 – 103 C. Identical in all other ways to that described above (General Procedure C).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60032-57-7, its application will become more common.

Reference:
Article; Roughley, Stephen D.; Browne, Helen; MacIas, Alba T.; Benwell, Karen; Brooks, Teresa; D’Alessandro, Jalanie; Daniels, Zoe; Dugdale, Sarah; Francis, Geraint; Gibbons, Ben; Hart, Terance; Haymes, Timothy; Kennett, Guy; Lightowler, Sean; Matassova, Natalia; Mansell, Howard; Merrett, Angela; Misra, Anil; Padfield, Anthony; Parsons, Rachel; Pratt, Robert; Robertson, Alan; Simmonite, Heather; Tan, Kiri; Walls, Steven B.; Wong, Melanie; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 901 – 906;,
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. 866546-07-8, name is 5-Chloro-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Chloro-1H-pyrrolo[2,3-b]pyridine

General procedure: In a microwave reaction vial with a magnetic stirring bar was placed the azaindoleor indole (0.38 mmol), aldehyde (0.19 mmol), and K2CO3 (176 mg, 1.27 mmol), followedby addition of 2.5 mL of 1:1 mixture of MeOH:H2O. The resulting mixture was placed ina microwave reactor and irradiated at 130 oC for 30 minutes. After cooling to roomtemperature, the volatiles were removed under reduced pressure. The crude residue wasdiluted with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combinedorganic layers were dried over sodium sulfate, filtered, and the resulting filtrate evaporated in vacuo to give a crude solid that was purified using reversed-phase HPLC,eluting with MeCN/H2O with a trace of TFA to give the desired compound.

The synthetic route of 866546-07-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uddin, Md. Imam; Buck, Jason R.; Schulte, Michael L.; Tang, Dewei; Saleh, Samir A.; Cheung, Yiu-Yin; Harp, Joel; Manning, H. Charles; Tetrahedron Letters; vol. 55; 1; (2014); p. 169 – 173;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem