Category: pyridine-derivatives

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.578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine, molecular formula is C6H5BrINO, molecular weight is 313.92, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-3-iodo-2-methoxypyridine

Intermediate compound10:ethyl 2-(5-bromo-2-methoxypyridin-3-yl)-5,5-dimethylcyclohex-1-enecarboxylate[360]Starting material8(1.14 g, 3.70 mmol), 5-bromo-3-iodo-2-methoxypyridine (1.40 g, 4.44 mmol), Pd(PPh3)4(0.85 g, 0.74 mmol) and cesium carbonate (2.41 g, 7.40 mmol) were dissolved in dioxane/water (v/v 9:1, 10 mL), and then reacted by microwave irradiation at 120 for 30 minutes. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, and then washed with a saturated ammonium chloride solution. The organic layer was dried with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure to remove the solvent. The residue was purified by MPLC (SiO2, EtOAc/hexane = 1:9) to obtain compound10(0.37 g, 27%) as colorless oil.[361]MS (ESI) m/z 368.0 (M++ H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,578007-66-6, 5-Bromo-3-iodo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jae Kwang; OH, Jung Taek; LEE, Jae Won; LEE, Seo Hee; KIM, Il-Hyang; LEE, Jae Young; BAE, Su Yeal; LEE, Se Ra; KIM, Yun Tae; WO2014/119947; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75806-86-9 ,Some common heterocyclic compound, 75806-86-9, molecular formula is C5H2BrClN2O2, 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.

5-Chloro-3-nitropicolinonitrile (104) 2-Bromo-5-chloro-3-nitropyridine (103) (6.0 g, 25 mmol) was mixed with copper (I) cyanide (4.6 g, 51 mmol) in a 100 mL round-bottom flask having a condensor loosely plugged with cotton was attached. The flask was slowly heated in an oil bath. When the temperature reaches approximately 150 C. (takes 2 h), the reaction mass begins to turn black. When the reaction mass turned completely black, the pressure was reduced to approximately 1 mm Hg by vacuum and the oil bath removed after 30 sec. (If the reaction goes too long, a vigorous reaction ensues, leaving little recoverable product.) The mixture was cooled to room temperature, and the sublimed solid (on the cotton) and reaction mass were treated with hot acetone (100 mL). The resulting mixture was gravity filtered, and the mother liquor rota-evaporated to dryness to yield the crude title compound as a dark brown solid. This solid can be purified by column chromatography using 4:1 hexane-EtOAc (Rf =0.13).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75806-86-9, its application will become more common.

Reference:
Patent; State of Oregon, Acting by and Through the Oregon State Board of Higher Education, Acting for and on Behalf of the Oregon Health Sciences University and the University of Oregon; Cocensys, Inc.; US5801183; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 51269-82-0, Adding some certain compound to certain chemical reactions, such as: 51269-82-0, name is 5-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 51269-82-0.

A mixture of 5-chloro-nicotinonitrile (63.8 mg, 461 mumol), 2-propanol (9.2 mL; not dry), and CaSO4 (-325 mesh) (920 mg, 6.76 mmol) was treated with a suspension of Raney Cobalt 2700 in 2-propanol under air (2 mL) (prepared by diluting 2 mL of the commercial water slurry with 15 mL 2-propanol, centrifuging, decanting, and repeating with 2×15 mL 2-propanol, then resuspending with 2 mL 2-propanol). The flask was then sealed and evacuated until bubbles formed, and the evacuated flask was flushed with H2 gas via balloon pressure. After 11 h stirring at rt under balloon H2 pressure, a NMR spectrum of a worked-up reaction aliquot indicated 80% conversion to the title compound. The reaction was then filtered, the filter cake was washed with 2-propanol (3×10 mL), and the combined clear colorless filtrates were concentrated briefly under rotary evaporation at 50 C. The residue was taken up in DCM and concentrated again to afford the volatile crude title compound (53 mg, 8 1%).

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. 51269-82-0, 5-Chloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Player, Mark R.; Lu, Tianbao; Hu, Huaping; Zhu, Xizhen; Teleha, Christopher; Kreutter, Kevin; US2007/225282; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 443956-08-9 ,Some common heterocyclic compound, 443956-08-9, molecular formula is C5H3BrN2O3, 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.

A mixture of 6-bromo-2-nitro-pyridin-3-ol (3 g, 13.7 mmol), Fe (7657.88 mg, 136.99 mmol) and NH4C1 (7329.1 mg, 136.99 mmol) in Ethanol (100 mL) and Water (100 mL) was stirred at 75 C for 2 hours to give a black suspension. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated to give the crude product (2.5 g, 13.22 mmol, 96.55% yield) as a solid. 1H NMR DMSO-c 400MHz deltaH = 9.71 (s, 1H), 6.74 (d, 1H), 6.50 (d, 1H), 5.92 (br 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. 443956-08-9, 6-Bromo-2-nitropyridin-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52378-63-9, (3-Aminopyridin-2-yl)methanol, 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: 52378-63-9, blongs to pyridine-derivatives compound. SDS of cas: 52378-63-9

i. A solution sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g) in aqueous hydrochloric acid (48% 10 ml) and water (5 ml) at 0-5 C. This solution of the diazonium salt was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric acid and following cessation of nitrogen evolution the mixture was heated on the steam bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. Filtration, concentration to low bulk and extraction with chloroform yielded 3-chloro-2-hydroxymethyl-pyridine (3.7 g), m.p. 42-44 (from n-pentane).

The synthetic route of 52378-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4024260; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1033810-70-6 , The common heterocyclic compound, 1033810-70-6, name is [1,2,4]Triazolo[1,5-a]pyridin-7-ol, molecular formula is C6H5N3O, 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.

Step F: Preparation of tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate: A vial charged with tert-butyl 3-chloro-2,4-difluorobenzoate (0.210 g, 0.845 mmol), [1,2,4]triazolo[1,5-a]pyridin-7-ol (0.114 g, 0.845 mmol), cesium carbonate (0.413 g, 1.27 mmol), and DMF (1.7 ml). The reaction was heated to 80 C for 12 hours, then poured into ice water. The resulting solids were collected by filtration and purified by flash chromatography, eluting with gradient of 10% EtOAc/ Hexanes to 50% EtOAc/Hexanes to provide the desired product.

The synthetic route of 1033810-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Array Biopharma, Inc.; EP2090575; (2009); 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. 55849-30-4, name is 5-Bromo-2-ethoxypyridine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-2-ethoxypyridine

General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

The synthetic route of 55849-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chelucci, Giorgio; Figus, Susanna; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 191 – 209;,
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 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Ethyl 6-Chloropyridine-3-acetate

Step 2 To a solution of ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 5.51 mmol) in dimethylformamide was added slowly sodium hydride (242 mg, 6.06 mmol) at 0 C., followed by iodomethane (821 mg, 5.79 mmol). The mixture was stirred at same degree for 1 hour, and then quenched with water. The resulting mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)propanoate (790 mg, 67%).

With the rapid development of chemical substances, we look forward to future research findings about 197376-47-9.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1186608-73-0, 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.1186608-73-0, name is 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine, molecular formula is C7H8N4, molecular weight is 148.17, as common compound, the synthetic route is as follows.

EXAMPLE 16: Tetra-butyl 3-(3-methyl-lH-pyrazolo r3.4-blpyridine-5- ylamino)piperidine- 1 -carboxylateTo a stirred solution of 3-Methyl-lH-pyrazole[3,4-¾]pyridn-5-amine (500mg, 3.3mmol) in EtOH (50ml), tert-butyl 3 -oxopiperidine-1 -carboxylate (74mg, l . lmmol) was added and reaction mass was cooled to 0C. Acetic acid (0.018ml, 0.33mmol) was added after which reaction mixture was stirred for 20 minutes. Sodium cyanoborohydride (42mg, 0.66mmol) was added and stirred for 12h at RT. TLC showed absence of SM. The reaction mixture was quenched with brine solution and extracted with ethyl acetate. The extract was washed with water and concentrated. Organic layer was dried over anhydrous sodium sulphate, dried and concentrated. Product was purified by flash column chromatography over 230-400 mesh silica gel using 2-5% MeOH/ DCM as eluent to afford the desired product 20, 500mg (Yield: 45%) as white solid. The product was confirmed by 1HNMR and MS spectrum analysis. 1H NMR (400 MHz, CDC13) delta: 8.13 (s, 1H), 7.19 (s, 1H), 3.95 (m, 1H), 3.25 (m, 1H), 3.43 (m, 1H), 3-3.25 (m, 2H), 2.52 (s, 3H), 2.15 (m. 1H), 1.78 (m, 1H), 1.6 (m, 2H), 1.49 (s, 9H); Ms- 331 (M-56), LCMS- 97%.

Statistics shows that 1186608-73-0 is playing an increasingly important role. we look forward to future research findings about 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine.

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 76015-11-7 ,Some common heterocyclic compound, 76015-11-7, molecular formula is C7H9NO2, 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.

a 2-Methyl-3-methoxy-4-chloropyridine N-oxide 11.2 g (80.5 mmol) of 3-methoxy-2-methyl-4(1H)-pyridone were heated under reflux for 10 hours in 100 ml of phosphorus oxychloride. Subsequently, the mixture was concentrated and 30 ml of toluene were added to each 2 ml volume; concentration then took place once again and the residue was taken up in 150 ml of water, with the pH of the mixture then being adjusted to 11 with K2 CO3; this mixture was then extracted with dichloromethane and the organic phase was washed with water, dried and freed from solvent. 8 g of the product were obtained, under standard conditions, from the pale brown oil (9 g) using m-chloroperbenzoic acid in dichloromethane, m.p. 88-89 C. (from petroleum ether).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76015-11-7, its application will become more common.

Reference:
Patent; Hoechst Aktiengesellschaft; US5658933; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem