Pyridine-derivatives

Related Products of 24484-93-3, 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. 24484-93-3, name is Methyl 4-chloropicolinate, molecular formula is C7H6ClNO2, 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.

Preparation of 2-Chloromethyl-4-chloropyridine To a slurry of lithium aluminum hydride (0.45 g, 11.9 mmol) in anhydrous diethyl ether (40 mL) at 0 C., a solution of methyl 4-chloro-pyridine-2-carboxylate (2.0 g, 11.7 mmol) in diethyl ether (30 mL) was added. The resulting mixture was stirred at room temp. overnight, and quenched with successive addition of water (0.45 mL), 15% aqueous NaOH (0.45 mL), and water (1.35 mL). The resultant slurry was stirred at room temp. for 30 min., and filtered through a small plug of Celite. The filtrate was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide 4-chloro-2-hydroxymethylpyridine.

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 24484-93-3, Methyl 4-chloropicolinate.

Reference:
Patent; Merck & Co., Inc.; US5891889; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6959-47-3, Adding some certain compound to certain chemical reactions, such as: 6959-47-3, name is 2-(Chloromethyl)pyridine hydrochloride,molecular formula is C6H7Cl2N, 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 6959-47-3.

General procedure: L1 was prepared by a similar procedure as described in the literature [24,39-41]. A water solution (15.0mL) of cyclopentylamine (1.70g, 0.020mol) was added to a water solution (15.0mL) of 2-picolylchloride hydrochloride (6.58g, 0.040mol) and an added NaOH pellet (3.20g, 0.080mol). After 5days of stirring at rt, the product was extracted with dichloromethane. The reaction solution was dried over MgSO4, then the filtrate solvent was removed under reduced pressure to give a brown oil (4.01g, 75.0

According to the analysis of related databases, 6959-47-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Dongil; Kim, Sunghoon; Kim, Eunhee; Lee, Ha-Jin; Lee, Hyosun; Polyhedron; vol. 63; (2013); p. 139 – 146;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 111669-25-1, 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. 111669-25-1, name is 1-Boc-4-(3-Aminopyridin-2-yl)piperazine, molecular formula is C14H22N4O2, 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 34.1 : 4-(3-Ethylamino-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester. To a mixture of 4-(3-amrno-pyridm-2-yl)-piperazme-l-carboxylic acid tert-butyl ester (2,0 g, 7.18 mmol), acetaldehyde (0.81 mL, 0.014 mol) and methanol (30 mL) was added sodium cyanoborohydride (1.36 g, 0.022 mol). The reaction mixture was stirred at room temperature for 2 days and then diluted with ethyl acetate, washed with water and washed with brine. The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel using hexanes: ethyl acetate (80:20) to give 4-(3-ethylamino-pyridm-2-yl)-piperazme-l-carboxylic acid tert-butyl ester (2.0 g, 91 %). GC/MS mfz 306, 223, 162, 150, 137, 120, 57.

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 111669-25-1, 1-Boc-4-(3-Aminopyridin-2-yl)piperazine.

Reference:
Patent; ASTRAZENECA AB; WO2008/112440; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 58481-11-1, name is Methyl 2-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H6ClNO2

Step 3 Preparation of 1-(2-Chloroisonicotinyl)-1,3-butanedione: To solution of methyl 2-chloroisonicotinate (12.0 g, 0.07 mol) and acetone (12.2 g, 0.21 mol) in 100 mL of dry THF at 35 C was added sodium methoxide portionwise. After heating the reaction mixture at reflux for 4 h, the solvent was removed. The residue was dissolved with 500 mL of water, acidified with acetic acid to pH=6 and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give 11.46 g (83percent yield) of product was a brown solid.

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, 58481-11-1, Methyl 2-chloroisonicotinate.

Reference:
Patent; Pharmacia Corporation; US6509361; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56622-54-9, 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.56622-54-9, name is (6-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, molecular weight is 122.17, as common compound, the synthetic route is as follows.

[0557] To a solution of compound VII (0.5 g, 1.39 mmol, 1 eq) in DMF (50 mL) were added HATU (0.7 g, 1.8 mmol, 1.3 eq) and DIPEA (0.74 mL, 4.17 mmol, 3 eq) under argon atmosphere at 0 C. A DMF solution of C-(6-methyl-pyridin-3-yl)-methylamine (0.25 g, 2.09 mmol, 1.5 eq) was added and the resulting mixture was stirred at 23 C for 16 h. The mixture was diluted with ice water (40 mL) and the organic components were extracted with EtOAc (2 x 50 mL) and 10% MeOH/CH2C12 (50 mL), and the combined extracts were washed with brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide the crude compound. The crude product was purified by flash Combiflash chromatography using 100-200 mesh silica gel eluting with 5% MeOH/CH2C12 to obtain compound (0.4 g, 62%) as an orange solid. 1H NMR (400 MHz, DMSO-d6) oe 9.53 (t, 1H, J = 6 Hz), 9.18 (s, 1H), 8.47 (s, 1H), 8.37 (s, 1H), 7.94 (s, 1H),7.70-7.44 (m, 2H), 7.23 (d, 1H, J = 8 Hz), 4.53 (d, 2H, J = 5 Hz), 2.45 (s, 3H). LCMS: m/z =463.0 [M+j, 465.0 [M+21, RT = 1.94 minutes; (Program Ri, Column W).

Statistics shows that 56622-54-9 is playing an increasingly important role. we look forward to future research findings about (6-Methylpyridin-3-yl)methanamine.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott; VENKATESAN, Aranapakam; PRIESTLEY, Tony; KUNDU, Mrinal; SAHA, Ashis; WO2015/95128; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1289197-78-9, 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 1289197-78-9, name is 2-Bromo-4-chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Example 195f 4-Chloro-2-(1-oxo-6,7,8,9-tetrahydropyrazino[1,2-a]indol-2(1H)-yl)nicotinaldehyde 195f A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (15 mL), 2-bromo-4-chloronicotinaldehyde 103a (503 mg, 2.28 mmol), 195e (142 mg, 0.76 mmol), cesium carbonate (490 mg, 1.5 mmol), CuI (143 mg, 0.76 mmol), and 4,7-dimethoxy-1,10-phenanthroline (127 mg, 0.52 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 80C for 10 hrs. It was then cooled to room temperature and filtered. The filtrate was washed with brine and concentrated under reduced pressure. The resulting residue was purified with silica-gel column chromatography eluting with 1:4 ethyl acetate/petroleum ether to afford 195f (160 mg, 65%) as a yellow solid. MS-ESI: [M+H]+ 328.

According to the analysis of related databases, 1289197-78-9, the application of this compound in the production field has become more and more popular.

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

Synthetic Route of 115309-57-4, 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.115309-57-4, name is tert-Butyl 6-chloronicotinate, molecular formula is C10H12ClNO2, molecular weight is 213.6608, as common compound, the synthetic route is as follows.

General procedure: To 6-chloronicotinic acid 19a (10 g) in methylene chloride(100 ml) solution, N,N?-diisopropyl-O-tert-butylisourea (50 g) wasadded and the mixture was stirred under heating and reflux for16 h. The insoluble compound was filtered out, and the filtratewas concentrated. The residue was purified by silica gel column chromatography (chloroform/ethyl acetate = 6/1) to obtain the compound 20a (11.66 g). To the compound 20a (6.0 g) in dimethylacetoamide (30 ml) solution, tris(dibenzylideneacetone)dipalladium (0.51 g), zinc cyanide (0.22 g), diphenylphosphinoferrocene (0.62 g), and zinc powder (1.98 g) were added and the mixture was stirred under argon atmosphere at 120 C for 3 h. The reaction solution was filtered by sellite, which was then washed with ethyl acetate. Then, the filtrate was washed with distilled water and saturated saline, then the organic layer was dried over with anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate= 5/1) to obtain the compound 21a (3.59 g). To copper(I) iodide(0.93 g) in tetrahydrofuran (50 ml) suspension, ethylmagnesium bromide (0.86 M tetrahydrofuran solution)(12.5 ml) was added dropwise under cooling at 0 C, the mixture was stirred at 0 C for 30 min, then the compound 21a (1.0 g) obtained above in tetrahydrofuran (10 ml) solution was added atthe 20 C. After stirring for 30 min at that temperature, 28% ammonia solution in water and ethyl acetate were added to the mixture and the solution separated. The aqueous layer was extracted with ethyl acetate, while the combined organic layer was washed with saturated saline, then was dried over with anhydrous sodium sulfate and concentrated. The obtained residue was purifiedby silica gel column chromatography (hexane/ethyl acetate= 8/1) to obtained the compound 22a (0.47 g). To the compound 22a (200 mg) in tetrahydrofuran (1 ml) solution, (-)-B-chlorodiisopinocampheylborane (65% hexane solution) (0.92 ml) was added dropwise under cooling at 20 C, then the mixture was stirred at that temperature for 18 h. Then, ether and distilled water were added to the reaction mixture, and the solution was separated. The organic layer was extracted with distilled water and 1 M hydrogen chloride. Then, the combined aqueous layer was neutralized by sodium hydrogen carbonate, and extracted with ethyl acetate. Organic layer was washed with saturated saline, then was dried over with anhydrous sodium sulfate and concentrated to obtained the title compound (150 mg, 84% ee). The optical purity was determined using CHIRALCEL AD-H(Daicel Chemical Industries) (movement phase: hexane/ethanol= 98/2, 1.0 ml/min).

Statistics shows that 115309-57-4 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 6-chloronicotinate.

Reference:
Article; Tanaka, Taisaku; Sugawara, Hajime; Maruoka, Hiroshi; Imajo, Seiichi; Muto, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 21; 14; (2013); p. 4233 – 4249;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 939-23-1, 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 939-23-1, name is 4-Phenylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 90 4-Phenylpyridine (15.5 g., 0.1 mole) dissolved in 185 ml. of absolute ethanol and 15 ml. of concentrated hydrochloric acid was reduced with hydrogen over 2 g. of platinum oxide under a hydrogen pressure of about 55 pounds p.s.i.g. The product was worked up in the manner described above in Example 72 and isolated in the form of the hydrochloride salt to give 15.3 g. of 4-cyclohexylpiperidine hydrochloride. (The free base gives m.p. 106-109 C.)

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 939-23-1, 4-Phenylpyridine.

Reference:
Patent; Sterling Drug Inc.; US4160862; (1979); A;,
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.942947-95-7, name is 2-Amino-5-bromo-4-chloro-3-nitropyridine, molecular formula is C5H3BrClN3O2, molecular weight is 252.45, as common compound, the synthetic route is as follows.HPLC of Formula: C5H3BrClN3O2

To a solution of tert-butyl 4-(2-(methyl(thiazol-2-yl)amino)-2-oxoethyl)piperazine-1-carboxylate (0.20 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (2.0 ml). The reaction mixture was stirred at room temperature for 1.5 h, then the solvents were removed under reduced pressure to afford N-methyl-2-(piperazin-1-yl)-N-(thiazol-2-yl)acetamide as the TFA salt that was dried in vacuo. To a mixture of this material (supposedly 0.20 mmol) and isopropanol (3.8 ml) was added 2-amino-5-bromo-4-chloro-3-nitropyridine (0.050 g, 0.20 mmol) followed by diisopropylethylamine (0.126 g, 0.97 mmol). The reaction mixture was stirred at 45 C. for 20 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 20% to 40% ethyl acetate in dichloromethane. The title compound was obtained as a yellow solid (0.042 g, 46%); 1H-NMR (500 MHz, DMSO-d6) 2.69 (br s, 4H, piperazine N(CH2)2), 3.08 (br s, 4H, piperazine N(CH2)2), 3.63 (s, 2H, NCH2CO), 3.70 (s, 3H, N-CH3), 6.98 (s, 2H, NH2), 7.27 (d, J=3.6 Hz, 1H, thiazole H), 7.53 (d, J=3.6 Hz, 1H, thiazole H), 8.17 (s, 1H, 6-H);LC (Method B)-MS (ESI, m/z) Rt=2.75 min-456, 458 [(M+H)+, Br isotopic pattern].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,942947-95-7, 2-Amino-5-bromo-4-chloro-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 884495-36-7, 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 884495-36-7, name is 6-Chloro-2-methylnicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-chloro-2-methylpyridine-3-carboxaldehyde (1.87 g, 12.0 mmol), (4- hydroxy-phenylsulfanyl)-acetic acid tert-butyl ester (2.48 g, 10.7 mmol) and K2CO3 (0.830 g, EPO 6.00 mmol) in DMF (20 mL) was heated at 125 C for 1 h. The mixture was cooled to room temperature and DMF was removed. Aqueous work-up and purification by flash chromatography on basic Al2O3 gel (CH2Cl2/hexanes, 1 :1 in v/v) afforded [4-(5-formyl-6- methyl-pyridin-2-yloxy)-phenylsulfanyl]-acetic acid tert-butyi ester as a pale yellow solid (0.481 g, 13%). 1H NMR (CDCl3) delta 1.42 (s, 9H), 2.72 (s, 3H), 3.56 (s, 2H), 6.78 (d, IH, J= 8.4 Hz), 7.09-7.13 (m, 2H), 7.46-7.50 (m, 2H), 8.11 (d, IH, J= 8.4 Hz), 10.24 (s, IH).

According to the analysis of related databases, 884495-36-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANORMED INC.; WO2007/22371; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem