Category: pyridine-derivatives

Electric Literature of 72830-09-2, 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. 72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride, molecular formula is C8H11Cl2NO2, 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.

EXAMPLE I 4 Preparation of 5-chloro-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (896 mg, 0.004 mol) was dissolved in 25 ml MeOH and treated with NaOH (390 mg, 0.008 mol) dissolved in 1.5 ml H2 O. 5-chloro-2-mercapto-1H-benzimidazole (812 mg, was added and the resulting mixture allowed to react for 2h at room temperature. The solvent was evaporated and the residue partitioned between 50 ml 2.5 % NaOH and 75 ml CH2 Cl2. The aqueous layer was separated and extracted twice with 25 ml CH2 Cl2. The organic layers were combined, washed with 25 ml H2 O, dried over MgSO and the solvent was evaporated. The crude product was triturated with approximately 5 ml of EtOAc saturated with NH3. The solid was collected and the mother liquor reprocessed furnishing 650 mg (48%) of the title compound as an off white powder. NMR data is given below.

According to the analysis of related databases, 72830-09-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AB Hassle; US4965269; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 624-28-2 ,Some common heterocyclic compound, 624-28-2, molecular formula is C5H3Br2N, 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.

Under argon atmosphere,848 mL of a diethyl ether solution of 50.9 g of Compound 1 was cooled, and 131 mL of a 1.64 mol / L n-BuLi hexane solution was added dropwise at -62 C. or lower over 30 minutes.After stirring for 30 minutes at the same temperature,21.5 g of dehydrated N, N-dimethylacetamide was added dropwise over 10 minutes.Aqueous ammonium chloride solution was added and stirred at room temperature for 2 days. Extract with ethyl acetate,After drying the organic layer over anhydrous magnesium sulfate,Concentrated under reduced pressure. Without further purification,Compound 2 was used in the next reaction as it was.

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. 624-28-2, 2,5-Dibromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Chartwell Medical Instrument Co., Ltd.; Ji, Bin; Higuchi, Masato; Suhara, Tetsuya; Chen, Chun-jen; Fujimoto, Osuke; (15 pag.)JP2019/123675; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7379-35-3 , The common heterocyclic compound, 7379-35-3, name is 4-Chloropyridine hydrochloride, molecular formula is C5H5Cl2N, 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.

1. (2.00 g, 8.76 mmol), 4-chloropyridine hydrochloride (1.31 g, 8.76 mmol) and TEA (2.44 ml, 17.55 mmol) were in /-PrOH (10 ml) and heated in the microwave for 2 h at 1200C. The solvent was removed under vacuum. The product was purified by column chromatography (silica gel, DCM/(7 M NH3 in MeOH, 99:1 –> 98:2 –> 95:5).

The synthetic route of 7379-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; MERLA, Beatrix; OBERBOeRSCH, Stefan; REICH, Melanie; SCHUNK, Stefan; JOSTOCK, Ruth; HEES, Sabine; ENGELS, Michael; GERMANN, Tieno; BIJSTERVELD, Edward; WO2010/99938; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 14254-57-0, 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. 14254-57-0, name is Isonicotinoyl chloride. A new synthetic method of this compound is introduced below.

General procedure: Compound 14 was prepared from 2f and isonicotinoyl chloride in a similar manner to that described for the synthesis of compound 3 and obtained in 28% yield as a white solid. M.p. 225-227 C. 1H NMR (400 MHz, DMSO-d6, T = 90 C) delta 0.59 (brs, 3H), 0.78 (brs, 4H), 1.40-1.59 (m, 2H), 2.24-2.36 (m, 1H), 2.63 (dt, J = 13.3, 6.8 Hz, 1H), 3.00 (s, 3H), 3.50 (dd, J = 12.5, 7.1 Hz, 1H), 4.23-4.36 (m, 1H), 6.76 (brs, 1H), 6.98-7.10 (m, 2H), 7.26 (brs, 2H), 8.58 (brs, 2H), 10.29 (brs, 1H). 13C NMR (151 MHz, DMSO-d6) delta 20.4, 23.5, 24.9, 33.0, 45.4, 50.8, 51.5, 57.4, 70.4 (d, JC-F = 1.1 Hz, 1C), 109.1 (d, JC-F = 7.7 Hz, 1C), 111.6 (d, JC-F = 24.9 Hz, 1C), 115.4 (d, JC-F = 23.2 Hz, 1C), 120.9 (s, 2C), 128.4 (d, JC-F = 7.7 Hz, 1C), 138.8 (s, 1C), 143.2 (s, 1C), 150.2 (2C) 157.6 (d, JC-F = 236.6 Hz, 1C), 165.7, 168.6, 175.0. MS m/z 426 (M+H)+. Anal. Calcd for C23H24FN3O4¡¤0.1H2O: C, 64.66; H, 5.71; N, 9.83. Found: C, 64.40; H, 5.80; N, 9.84.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14254-57-0, Isonicotinoyl chloride, and friends who are interested can also refer to it.

Reference:
Article in Press; Ito, Masahiro; Iwatani, Misa; Yamamoto, Takeshi; Tanaka, Toshio; Kawamoto, Tomohiro; Morishita, Daisuke; Nakanishi, Atsushi; Maezaki, Hironobu; Bioorganic and Medicinal Chemistry; (2017);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55589-47-4, 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. 55589-47-4, name is 3-Methylpicolinaldehyde, molecular formula is C7H7NO, 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.

The compound (104.9 mg) obtained in Example 47-3 was dissolved in methanol (3.2 ml) and then added with the compound (36.3 mg) obtained in Example 53-1 and sodium cyanoborohydride (31.4 mg). Then, the solution was adjusted to pH 5 with acetic acid and then stirred at room temperature for 14 hours. After completion of the reaction, a 1 mol/l sodium hydroxide aqueous solution was added to the reaction solution, followed by separation/extraction with chloroform. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and then treated with hydrochloric acid, thereby obtaining hydrochloride (91.5 mg) of the subject compound as a white solid. MS(FAB,Pos.)m/z=525[M+H]+1H-NMR(500MHz,DMSO-d6) :delta=0.88(6H,t,J=7.3Hz),1.60-1.80(4H,m),2.37(3H,s),2.95(4H,t,J=7.1Hz),3.84(2H,s),4.16(2H, s),4.25(2H,s),4.28(2H,s),7.53(2H,d,J=8.5Hz),7.55(2H,d,J=8.3H z),7.62(2H,s),7.76(1H,dd,J=4.8,7.6Hz),7.83(2H,d,J=8.5Hz),7.8 6(2H,d,J=8.3Hz),8.22(1H,d,J=7.6Hz),8.65(1H,d,J=4.9Hz).

According to the analysis of related databases, 55589-47-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
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 94166-64-0, name is 2-Chloro-6-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H3ClN2O2

To a solution of 2-chloro-6-nitropyridine (2.0g, 22.96mmol, 1.5eq) and 3-methoxyazetidine (2.43g, 15.30mmol, l .Oeq) in dimethyl sulfoxide (20mL) was added sodium bicarbonate (2.57g, 30.60mmol, 2.0 eq). Reaction mixture was stirred at 80C for 4h. After completion of reaction, reaction mixture was transferred into water and extracted with ethyl acetate. Organic layer was combined, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted in 20% ethyl acetate in hexane as eluant to obtain pure 98.1 (2.0g, 62.47 %). MS(ES): m/z 210.21 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 94166-64-0.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 69214-09-1, 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.69214-09-1, name is 5-Bromoimidazo[1,2-a]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.

Method 33 3-Acetvl-5-bromoimidazo[1,2a]pyridine Aluminium chloride (10.2g, 77mmol) was added in portions over 10 minutes to a solution of 5-bromoimidazo[1,2a]pyridine (Method 32; 5.0g, 26mmol) in dichloromethane (100ml) cooled to 0C. The mixture was heated to reflux and acetyl chloride (2.54ml, 36mmol) was added over 15 minutes. The mixture was heated at reflux for 24 hours, cooled to 0C, and further aluminium chloride (10.2g, 77mmol) followed by acetyl chloride (3.26ml) were added. The mixture heated at reflux for 24 hours and then the volatiles were removed by evaporation. Iced water was added, the mixture was basified with 2M aqueous sodium hydroxide solution and extracted with ethyl acetate. The extracts were washed with water, dried and the solvent evaporated to the title compound which was used without further purification 4.0g. NMR: 2.58 (s, 3H), 7.74-7.82 (m, 2H), 8.62 (s, 1H), 9.62 (s, 1H); m/z: 241 [MH]+

Statistics shows that 69214-09-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromoimidazo[1,2-a]pyridine.

Reference:
Patent; AstraZeneca AB; EP1214318; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56809-84-8 ,Some common heterocyclic compound, 56809-84-8, molecular formula is C5H2Cl2N2O2, 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 stirred solution of tert-butyl 4-aminopiperidine-1-carboxylate (4.47 g, 22.39 mmol) in DMF (60 mL) were added DIPEA (4.68 mL, 26.87 mmol) and 3,4-dichloro-5-nitropyridine (4.3 g, 22.39 mmol) and the resulting reaction mixture was stirred at 80 C for 16 h. The reaction mixture was cooled to room temperature and diluted with chilled water and the organic components were extracted in EtOAc. The organic layer was washed water, brine and dried over anhyd. Na2504. The organic layer was then concentrated in vacuo to obtain crude product as dark brown oil. The crude material was purified by silica gel (100-200 mesh) column chromatography using 20% EtOAc/Hexane as eluent to afford the title compound (2 g, 25%) as a solid.

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. 56809-84-8, 3,4-Dichloro-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDIVIR AB; AYESA, Susana; ERSMARK, Karolina; KALAYANOV, Gennadiy; LEIJONMARCK, Marie; SALVADOR ODEN, Lourdes; WESTERLIND, Hans; WAeHLING, Horst; BERTRAND, Megan; BROCHU, Christian; GHIRO, Elise; KUHN, Cyrille; STURINO, Claudio; BYLUND, Johan; SEHGELMEBLE, Fernando; (215 pag.)WO2017/18924; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1289197-78-9, 2-Bromo-4-chloronicotinaldehyde, 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, SDS of cas: 1289197-78-9, blongs to pyridine-derivatives compound. SDS of cas: 1289197-78-9

Example 192c 4-Chloro-2-(4-oxo-7,8,9,10-tetrahydropyridazino[4,5-a]indolizin-3(4H)-yl)nicotinaldehyde 192c A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (50 mL), potassium carbonate (1.5 g, 10.6 mmol), 7,8,9,10-tetrahydropyridazino[4,5-a]indolizin-4(3H)-one 192b (1.0 g, 5.3 mmol), and 2-bromo-4-chloronicotinaldehyde (3.5 g, 15.9 mmol). After bubbling nitrogen through the resulting mixture for 30 minutes, copper(I) bromide (75.0 mg, 0.53 mmol) and sarcosine (47.0 mg, 0.53 mmol) were added, and the reaction mixture was heated at 95C for 12 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was partitioned between methylene chloride (60 mL) and water (40 mL). The aqueous layer was separated and extracted with methylene chloride (3 x 70 mL). The combined organic layer was washed with brine (30 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 10:1 ethyl acetate/petroleum ether to afford 192c as a brown solid (521 mg, 30%). MS-ESI: [M+H]+ 329.2.

The synthetic route of 1289197-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 98198-48-2, 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 98198-48-2 as follows.

Step A: N-(‘5-bromo-4-methylpyridin-2-yl -2,2-dimethylpropanamide: To a solution of 5- bromo-4-methylpyridin-2-amine (20.6 g, 1 10 mmol) in 80 mL of pyridine was added trimethylacetyl chloride (19.9g, 165 mmol) dropwise. The reaction mixture was allowed to stir at room temperature for 12 hours. The mixture was diluted with water and extracted with dichloromethane (3 x). The organic layers were washed with water (2 x) and brine, dried over Na2S04 and concentrated to provide crude product, which was purified by chromatography. On elution with 2->20% EtOAc / hexanes N-(5-bromo-4-methylpyridin-2-yl)-2,2- dimethylpropanamide was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98198-48-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alexander; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda, K.; SUZUKI, Takao; WO2015/100147; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem