Pyridine-derivatives

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. 22282-96-8, name is 2-Bromo-6-methyl-5-nitropyridine. A new synthetic method of this compound is introduced below., Formula: C6H5BrN2O2

A suspension of 6-bromo-2-methyl-3-nitropyridine (XIV) (250 g, 1.15 mol, 1.00 eq) and NH4C1 (300 g, 5.61 mol, 4.88 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 65C. To this mixture was added Fe (130 g, 2.33 mol, 2.02 eq) and HQ (15.3 g, 419 mmol, 0.36 eq). The suspension was then heated to 80C for another 3 h. The reaction was cooled to 25C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 L x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6- bromo-2-methylpyridin-3-amine (XV) as brown solid (373 g, 1.99 mol, 86.7% yield) which was used for the next step without any purification. NMR (DMSO-de, 400 MHz) delta ppm 6.01 (dd, J = 2.3, 7.9 Hz, 2H), 7.03 (d, J= 8.2 Hz, IH); ESIMS found for C6H7BrN2 mlz 186.8 (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, 22282-96-8, 2-Bromo-6-methyl-5-nitropyridine.

Reference:
Patent; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (230 pag.)WO2017/24025; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, 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: 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-(trifluoromethyl)pyridin-3-amine

2-Chloro-3-N-isopropylamino-5-(trifluoromethyl)pyridineTo a solution of 2-chloro-3-amino-5(trifluormethyl)pyridine (0.78 g, 3.97 mmol) in dichloromethane (10 ml) are added subsequently at 0C glacial acetic acid (5 ml), acetone (0.62 g, 10.7 mmol) and borane-dimethyl sulfide (0.33 g, 4.37 mmol). After warming to room temperature the resulting solution is stirred for 16 h. The reaction mixture is cooled to 0 C, and then a 25 % aqueous ammonia solution is added until a pH of 8 is reached. After addition of water (5 ml) the aqueous phase is removed and extracted three times with dichloromethane (40 ml). The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness. Yield: 0.60 g (63 %).1H-NMR(CD2CI2, 400 MHz: delta = 1.28 (d, 6H), 3.60-3.72 (m,1 H), 4.5 (br s, 1 H), 7.02 (s, 1 H), 7.89 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; BASF (CHINA) COMPANY LIMITED; METZ, Stefan; FUCHS, Evelyn; DORMANN, Korinna; MOLT, Oliver; LENNARTZ, Christian; WAGENBLAST, Gerhard; GEssNER, Thomas; SCHILDKNECHT, Christian; WATANABE, Soichi; WO2012/172482; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64951-08-2, 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.64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.

Imidazo[l,2-a]pyridine-2-carboxylic acid (500 mg, 3.1 mmol) was dissolved in ethanol (20 ml) and platinium oxide (100 mg) was added, and the mixture hydrogenated at 4 bar overnight. The mixture was filtered, and the filtrate evaporated to dryness to afford the sub-title compound (500 mg, 97%). 1H NMR (400 MHz, DMSO-J6) delta 7.63 (s, IH), 3.96 (t, 2H), 2.70 (t, 2H), 1.85 (m, 4H).

The chemical industry reduces the impact on the environment during synthesis 64951-08-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2007/108750; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 23056-47-5, 2-Bromo-4-methyl-5-nitropyridine, 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, Product Details of 23056-47-5, blongs to pyridine-derivatives compound. Product Details of 23056-47-5

2-Bromo-4-methyl-5-nitropyridine (2.5g, 11.58mmol) was dissolved in concentrated sulfuric acid (25mL), cooled to ice bath 0C, chromium trioxide (3.88g, 38.8mmol) was added. It was slowly warmed to room temperature and stirred overnight. The reaction mixture was poured into ice water (75 mL), stirred for 10 minutes and suction filtered to give a white solid (2.5g, yield: 87.8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23056-47-5, 2-Bromo-4-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Yang Xiaoju; (118 pag.)CN109575016; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 877133-54-5, 4-Bromo-2,6-diethylpyridine, 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: 4-Bromo-2,6-diethylpyridine, blongs to pyridine-derivatives compound. Recommanded Product: 4-Bromo-2,6-diethylpyridine

Zinc cyanide (546 mg, 4.67 mmol) was added to a degassed solution of 4-bromo-2,6- diethylpyridine (500 mg, 10.8 mmol) and tetrakis(triphenylphoshpine) palladium (137 mg, 0.17 mmol) in dry DMF (5 ml_). The resulting reaction mixture was heated at 100C for 16 h. The mixture was cooled to room temperature, diluted with ethyl acetate (15 ml_) and filtered through Celite. The filter cake was washed with ethyl acetate (2 x 10 ml_). The combined organic filtrate was washed with water (10 ml_) and saturated aqueous NaCI, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with 40% to 60% ethyl acetate in petroleum ether, to afford 2,6-diethylisonicotinonitrile (270 mg, 73%). 1H NMR: 6H (300 MHz, DMSO-c/6) 7.56 (2H, s), 2.77 (4H, q, J 7.5), 1.23 (6H, t, 7.5).

The synthetic route of 877133-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MIRONID LIMITED; ADAM, Julia Mary; ADAMS, David Roger; KULKARNI, Santosh Shripad; NANDURDIKAR, Rahul Shripad; (131 pag.)WO2019/193342; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 116855-08-4, 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.116855-08-4, name is 1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H5N3O2, molecular weight is 163.13, as common compound, the synthetic route is as follows.

To a solution of 1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XV) (0.39 g, 2.4 mmol) in dry MeOH (10 mL) was added concentrated H2SO4 (4 drops) and refluxed for 6 h under nitrogen. The solution was cooled and the solvent was evaporated under vacuum. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified on a flash silica gel column (100% DCM?3:97 MeOH:DCM) to produce methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XVI) as a white solid (382 mg, 2.16 mmol, 90% yield). 1H NMR (CDCl3) delta ppm 4.08 (s, 3H), 7.38 (m, 1H), 8.63 (dd, J=8.10 Hz, J=1.51 Hz, 1H), 8.72 (dd, J=4.62 Hz, J=1.41 Hz, 1H); ESIMS found for C8H7N3O2 m/z 178.2 (M+H)

Statistics shows that 116855-08-4 is playing an increasingly important role. we look forward to future research findings about 1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; US2013/296302; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 380380-64-3, 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. 380380-64-3, name is 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, molecular formula is C7H6BrN5, 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.

Under the protection of nitrogen, add 17.7g of 2-methyl-5- (5-bromopyridin-2-yl) tetrazole, 27.7g of borate intermediate, 0.663g of tricyclohexylphosphine and 0.23L of dioxane Stir to dissolve; add a solution of potassium carbonate 175g in water 70mL at one time; add 0.88g of tris (dibenzylideneacetone) dipalladium, vacuum-nitrogen replacement three times, then heat the reaction to 70C, and keep the reaction for 1 hour, filter the reaction Liquid, rinse, add 15% saline solution to the mother liquor (the mass concentration refers to the mass of sodium chloride as a percentage of the total mass of saline solution) 100mL, separate layers, separate organic phase, and concentrate in vacuum (temperature 45 65 , pressure -0.08MPa -0.1MPa) to dry, the crude product is stirred in ethyl acetate 120mL) for 12 hours to 16 hours and filtered, and the wet product is dried in a vacuum (pressure -0.01MPa -0.1MPa) oven Dry at 45 C to 55 C for 8 hours to 12 hours to obtain 26.0 g of off-white solid as terdazolamide phosphate II, with a total yield of 55.1% (based on benzyl 3-fluoro-4-bromophenylcarbamate) ). HPLC purity 96.23%.

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 380380-64-3, 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine.

Reference:
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Chen Jian; Liu Zhenfeng; Ying Shuhuan; (16 pag.)CN110804038; (2020); A;,
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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine, molecular formula is C6H6F3N3, 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. HPLC of Formula: C6H6F3N3

[(C)] [6-TRIFLUOROMETHYL-1,] 3-diliydro-imidazo [4,5-b] pyridin-2-one, trifluoroacetic acid salt. A mixture of 5-trifluoromethyl-pyridine-2, 3-diamine from step (b) above and N, [N-CARBONYLDIIMIDAZOLE] (938 mg, 579 mmol, Aldrich) in THF (10 mL) was stirred at room temperature for 16 h. The reaction mixture was diluted with [HA0] (20 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were concentrated in vacuo and the residue was purified by preparative HPLC (gradient 0. [1 %] trifluoroacetic acid in acetonitrile) to give the title compound. MS (ESI positive ion) m/z: 204 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 107867-51-6.

Reference:
Patent; AMGEN INC.; WO2004/35549; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6945-67-1 ,Some common heterocyclic compound, 6945-67-1, molecular formula is C5H3BrN2O2, 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.

Combine 2-bromo-4-nitropyridine (1.00g, 4.93mmol), 4-methylpiperidin-4-ol(709.23mg, 6.16mmol) and cesium carbonate(2.41g, 7.39mmol) dissolved in 30mL In 1,4-dioxane solution, react overnight at 100C. LC-MS detection, the reaction is over,Cool to room temperature, filter, concentrate the filtrate and purify by column chromatography to obtain the title compound.

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. 6945-67-1, 2-Bromo-4-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Wang Yazhou; Quan Xu; Liu Haixuan; Wang Xiaowei; Zhang Yan; Li Xue; Cao Chen; Guo Zhuang; Lv Kunzhi; Wang Hai; Zheng Guochuang; (126 pag.)CN111196804; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 182181-42-6, 2-(Chloromethyl)-8-methylimidazo[1,2-a]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, 182181-42-6, blongs to pyridine-derivatives compound. SDS of cas: 182181-42-6

67(D) 8-Methyi-2-(4-(trimethyisiiyi)but-3-ynyl)-imidazo[1,2-a]pvridine ;To a solution of trimethyl(prop-1-ynyl)silane (259 mg, 2.31 mmol) in THF (7.5 mL) at -78C was added n-BuLi 2.5M in hexane (1.1 mL, 2.8 mmol). After 90min at -78C 2-(chloromethyl)-8-methyl-imidazo[1,2-a]pyridine (500 mg, 2.8 mmol) in THF (5 mL) was added dropwise. The solution became blue-green at-78C. The solution was stirred at-78C for an additional 1h. The reaction was quenched with water and the solvent was removed under reduced pressure. The crude product was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH from 100/0 to 99/1 as eluent) to afford 590 mg of 8-methyl-2-(4-(trimethylsilyl)but-3-ynyl)- imidazo[1,2-a]pyridine (Yield : 100%) as an yellow oil. LCMS (RT) : 0.59-2.61min; MS (ES+) gave m/z : 257.1 Rf (DCM/MeOH : 95/5) : 0.22

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,182181-42-6, its application will become more common.

Reference:
Patent; ADDEX PHARMACEUTICALS SA; WO2005/123703; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem