Category: pyridine-derivatives

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. 1289197-78-9, name is 2-Bromo-4-chloronicotinaldehyde, the common compound, a new synthetic route is introduced below. Safety of 2-Bromo-4-chloronicotinaldehyde

Example 170b 4-Chloro-2-[(1R,11S)-7-oxo-3,6-diazatetracyclo[9.2.1.02,10.03,8]tetradeca-2(10),8-dien-6-yl]pyridine-3-carbaldehyde 170b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (30 mL), (1S,11R)-3,6-diazatetracyclo[9.2.1.02,10.03,8]tetradeca-2(10),8-dien-7-one 170a (400 mg, 2.0 mmol), 2-bromo-4-chloronicotinaldehyde 103a (1.30 g, 6.0 mmol), and potassium acetate (390 mg, 4.0 mmol). After bubbling nitrogen through the resulting mixture for 30 minutes, Xantphos (110 mg, 0.20 mmol) and tris(dibenzylideneacetone)dipalladium(0) (180 mg, 0.20 mmol) were added, and the reaction mixture was heated at 80 C for 10 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was partitioned between ethyl acetate (50 mL) and water (30 mL). The aqueous layer was separated and extracted with ethyl acetate (3 X 30 mL). The combined organic layer was washed with brine (20 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 2:1 petroleum ether/ethyl acetate to afford 170b (405 mg, 59%) as a yellow solid. MS-ESI: [M+H]+ 342.2

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 100367-39-3, 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. 100367-39-3, name is 4-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, 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.

4-BromoBromo-2-methoxypyridine (3.06 g, 16.2 mmol), (6- (trifluoromethyl)pyridin-3-yl)methanol (2.74 g, 15.5 mmol), 3,4,7,8- tetramethylphenanthroline (0.36 g, 0.15 mmol), CuI (0.14 g, 0.74 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were combined in toluene (15 mL) and heated to reflux under a nitrogen Attorney’s Docket 2882.023B atmosphere for 16 h. Upon cooling the mixture was purified by flash column chromagraphy (silica gel, hexanes/EtOAc, 1 :0 to 1 :1) to provide the title compound (3.19 g, 72%) as a red oil: 1H NMR (300 MHz, CDCl3) delta 8.78 (s, IH), 8.02 (d, J= 5.9 Hz, IH), 7.95 (d, J= 8.1 Hz, IH), 7.32 (d, J= 8.0 Hz, IH), 6.55 (dd, J= 5.9, 2.2 Hz, IH), 6.26 (d, J = 2.2 Hz, IH), 5.16 (s, 2H), 3.93 (s, 3H).

According to the analysis of related databases, 100367-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66572-56-3, Adding some certain compound to certain chemical reactions, such as: 66572-56-3, name is 2-Bromoisonicotinic acid,molecular formula is C6H4BrNO2, 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 66572-56-3.

A solution of 2-bromoisonicotinic acid (5.00 g, 24.8 mmol) in MeOH (50 mL) was treated with sulfuric acid (0.50 mL, 9.4 mmol) and the reaction mixture was stirred at 80 C for 1 hour. The mixture was returned to room temperature and stirred for a further 96 hours before heating to 80 C and stirring for 24 hours. The reaction mixture was cooled to room temperature, and the volatiles were removed in vacuo. An aqueous NaOH solution (2 M, -50 mL) was added to the residue and the aqueous was extracted with EtOAc (3 * 50 mL). The organic layers were combined, washed with brine, dried (MgS04) and the solvent removed in vacuo to give the title compound as a yellow oil (4.14 g, 77%). LCMS-B: rt 3.55 min; m/z 216 [Mu+Eta for /9Br. 218 [M+H]+ for 81 Br; 1H NMR (400 MHz, CDCb) delta 8.52 (dd, J = 5.0, 0.8 Hz, 1 H), 8.04 (t, J = 1.2 Hz. 1 H), 7.80 (dd, J = 5.0, 1.4 Hz, 1 H), 3.96 (s, 3H).

According to the analysis of related databases, 66572-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LTD; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; WALKER, Scott Raymond; LAGIAKOS, H. Rachel; (98 pag.)WO2016/34675; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1101120-05-1, 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. 1101120-05-1, name is 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile, molecular formula is C9H5N3O, 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.

General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

According to the analysis of related databases, 1101120-05-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Frederick, Raphael; Marshall, Elaine S.; Singh, Ripudaman; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 58 – 68;,
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.106984-91-2, name is 6-Oxo-1,6-dihydropyridine-3-carbaldehyde, molecular formula is C6H5NO2, molecular weight is 123.11, as common compound, the synthetic route is as follows.Recommanded Product: 6-Oxo-1,6-dihydropyridine-3-carbaldehyde

Example 22: [Show Image] To a solution of intermediate 22b (295 mg, 0.720 mmol) in acetonitrile (20 mL) and acetic acid (200 muL) was added 6-hydroxynicotinaldehyde (87 mg, 0.708 mmol). The reaction mixture was stirred vigorously at reflux temperature overnight. The solvent was removed under reduced pressure. The crude product was purified by preparative LC-MS. The pure product (54 mg, orange oil) was dissolved in methanol (2 mL) and 1 M HCl in diethyl ether (110 muL, 0.110 mmol) was added. The solvents were removed under reduced pressure. The product was taken up in water (3 mL) and lyophilized.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,106984-91-2, 6-Oxo-1,6-dihydropyridine-3-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; EP2439197; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 57266-69-0, 3-Chloropicolinic acid, 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, 57266-69-0, blongs to pyridine-derivatives compound. Quality Control of 3-Chloropicolinic acid

To a solution of 3-chloropyridine-2-carboxylic acid (2.1 g, 13.33 mmol, 1.00 equiv) in THF (40 mL) was added Et3N (2.7 g, 26.68 mmol, 2.00 equiv), followed by the addition of chloro(propan-2-yloxy)methanone (2.45 g, 19.99 mmol, 1.50 equiv) dropwise with stirring at 0 C. The solution was strried for 1 h at room temperture. The solid was removed by filtration. To the filtrate was added NaBH4 (1.53 g, 40.44 mmol, 3.00 equiv). The resulting solution was stirred for 2 h at rt, then diluted with 50 mL of H2O and extracted with 2*100 mL of EtOAc. The combined organic layers were washed with 50 mL of saturated Nacl, dried over Na2SO4, concentrated under vacuum, and purified with silica gel chromatography using with EtOAc/petroleum ether (1:6) to afford 0.9 g (47%) of the title compound as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57266-69-0, its application will become more common.

Reference:
Patent; Vettore, LLC; PARNELL, Kenneth Mark; MCCALL, John; ROMERO, Donna; (172 pag.)US2018/162822; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16063-70-0 ,Some common heterocyclic compound, 16063-70-0, molecular formula is C5H2Cl3N, 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 30.74 g of potassium tert-butoxide in 100 ml of dimethylsulfoxide, 16.72 g of nitromethane was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 1 hour. Then, the reaction mixture was cooled with ice again, and to the reaction mixture, 25.00 g of 2,3,5-trichloropyridine in 100 ml of dimethylsulfoxide was added dropwise with stirring, and after the addition, the mixture was stirred at 70C for another 6 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, poured into 200 ml of 10% aqueous hydrochloric acid with stirring under cooling with ice and extracted with ethyl acetate (200 ml*1). The resulting organic layer was washed with water (100 ml*1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 5:95 to 10:90) as the eluent to obtain 10.10 g of the desired product as a pale yellow oil. 1H NMR (CDCl3, Me4Si, 300MHz) delta8.53 (d, J=2.4Hz, 1 H), 7.84 (d, J=2.4Hz, 1 H), 5.76 (s, 2H).

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. 16063-70-0, 2,3,5-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nissan Chemical Industries, Ltd.; IWASA, Motoyoshi; TSUJI, Keisuke; TOMIZAWA, Mitsutaka; MITA, Takeshi; KUWAHARA, Hidehito; ASAHI, Miho; IMANAKA, Hotaka; EP2873658; (2015); 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. 117977-21-6, name is 2-[[[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl ]methyl]thio]-1H-benzimidazole, molecular formula is C18H21N3O2S, 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. COA of Formula: C18H21N3O2S

50 g of 2-[4-(3-methoxy propoxy-3-methylpyridine-2-yl) methyl thio]- lH-benzimidazole was taken in 100 ml acetonitrile. To this mixture 185.2 g (0.95mol) sodium hypochlorite was added drop wise between 0-50C in a nitrogen atmosphere and the obtained mixture was stirred at 0-50C for 30 minutes. After completion of reaction, the pH of reaction mixture was adjusted to 9.0 by using 5 % acetic acid. The mixture was extracted with methylene dichloride, and the extract was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and dried under vacuum. The obtained residue was dissolved in 20 ml of methylene dichloride followed by t-butyl methyl ether to get the clear solution. Stir the mass for one hour at room temperature to get the precipitate. Filtered the precipitated product and washed with 100 ml of t-butyl methyl ether. Dry the product at 600C under vacuum to obtain title compound 41 g (78.25%) as off white solid

With the rapid development of chemical substances, we look forward to future research findings about 117977-21-6.

Reference:
Patent; IPCA LABORATORIES LIMITED; WO2009/116072; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 609-71-2, 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. 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

Step 1 Methyl 2-hydroxynicotinate 2-Hydroxynicotinic acid (2.50 g, 17.97 mmol) was dissolved in methanol (20.00 mL), added with sulfuric acid (18M, 47.90 uL), and then stirred at 70 C. under nitrogen atmosphere for 12 hours. After the reaction mixture was concentrated, the residue was dissolved in dichloromethane (50.00 mL) and the system was adjusted to pH=8 with saturated sodium bicarbonate solution. A white solid was slowly precipitated and filtered to give methyl 2-hydroxynicotinate (a white solid, 1.5 g, yield: 54.51%). 1H NMR (400 MHz, CDCl3) 8.27 (dd, J=2.0, 7.0 Hz, 1H), 7.78 (dd, J=2.0, 6.0 Hz, 1H), 6.41 (t, J=6.8 Hz, 1H), 3.90 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,609-71-2, 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 105752-11-2, 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 105752-11-2, name is 3-Amino-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

A reselable pressure tube was charged with 4-iodopyridin-3 -amine (2.4 g, 10.9 mmol), 4-(triethylsilyl)but-3-yn-ol (5.0 g, 27.3 mmol), lithium chloride (0.46 g, 42.0 mmol), sodium carbonate (2.31 g, 21.8 mmol) and 1,1 ‘- bis(diphenylphosphino)ferrocenopalladium(II) dichloride, toluene (0.45 g, 0.55 mmol), the tube was sealed and heated on a 100 C oil bath for ~20h. The reaction mixture was cooled to ambient temperature, diluted with EtOAc (75 mL) and ether (75 mL). Water (150 mL) was added and the biphasic mixture was filtered through celite. The filtrate was transferred to a separatory funnel and the phases were separated and the aqueous fraction extracted twice more with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by silica gel chromatography, eluting with 2-20% (9: 1 MeOH/NH4OH)/chloroform, affording 2- (2-(triethylsilyl)-lH-pyrrolo[2,3-c]pyridin-3-yl)ethanol (2.45 g, 81% yield). LCMS method A: retention time = 3.44 min, M+H = 277.25. 1H NMR (400MHz, CHLOROFORM-d) delta = 8.79 (s, 1H), 8.65 – 8.47 (m, 1H), 8.22 (d, J=5.5 Hz, 1H), 7.56 (d, J=5.3 Hz, 1H), 3.91 (t, J=6.9 Hz, 2H), 3.13 (t, J=6.9 Hz, 2H), 1.82 (br. s, 1H), 1.12 – 0.90 (m, 15H).

According to the analysis of related databases, 105752-11-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar M.; ZUSI, F. Christopher; OLSON, Richard E.; WO2015/191403; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem