Day: April 15, 2022

Adding a certain compound to certain chemical reactions, such as: 1122-43-6, 2,6-Dimethyl-3-hydroxypyridine, 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, 1122-43-6, blongs to pyridine-derivatives compound. Product Details of 1122-43-6

Step A: 2,6-Dimethylpyridin-3-ol (1.0 g, 8.1 mmol) was dissolved in aqueous NaOH (4.05 mL, 2 M, 8.1 mmol). To the solution was added iodine (2.62 g, 10.3 mmol) at room temperature. The mixture was stirred at 50 C. for 2 h, then neutralized (pH ?7) with aqueous HCl (2 N). Excess reagent was quenched with sodium thiosulfate, then the solvent was removed under vacuum. The residue was suspended in 10% MeOH in CH2Cl2 (100 mL) and filtered. The filtrate was concentrated to give 4-iodo-2,6-dimethylpyridin-3-ol (0.96 g, 50%). MS m/z 250.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 403-45-2 ,Some common heterocyclic compound, 403-45-2, molecular formula is C6H4FNO2, 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.

Methyl 6-fluoronicotinate. To a solution of 6-fluoronicotinic acid (255 mg, 1.32 mmol) in methanol (5 mL) at room temperature was added (trimethylsilyl)diazomethane (4.0 mL, 2 M in diethyl ether, 8.0 mmol). The reaction mixture was stirred at room temperature for 30 min and concentrated. Methyl 6- fluoronicotinate (129 mg, 47%) was used without further purification: 1H NMR (600 MHz, DMSOd6) delta 8.79 (d, J = 2.6 Hz, IH), 8.47 (td, J = 7.9, 2.6 Hz, IH), 7.35 (ddd, J = 8.5, 2.6, 0.6 Hz, IH), 3.88 (s, 3H); ESIMS calcd 156.0 (M+ + H), found 156.1 (M+ + H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,403-45-2, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; ATON PHARMA, INC.; WO2007/2248; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75711-01-2, 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 75711-01-2, name is 6-Chloro-5-methoxypyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

To an ice-cooled suspension of 6-chloro-5-(methyloxy)-3-pyridinamine D46 (2.14 g, 13.50 mmol) in HCl 4 M in water (10.12 ml, 40.50 mmol), a solution of sodium nitrite (1.02 g, 14.84 mmol) in water (7 ml) was added dropwise over a 5 min period and the resulting mixture was vigorously stirred at 5 C. for 30 min. To the mixture at 5 C. was added a solution of NaBF4 (2.67 g, 24.29 mmol) in water (17 ml). The thick suspension was collected by filtration, washed with cold water and a little amount of cold EtOH and dried under reduced pressure at 55 C. for 8 h. The resulting black solid was taken-up in xylenes (25 ml) and allowed to reflux for 1 h. The solvent was evaporated under reduced pressure, the residue dissolved in EtOAc and washed with a saturated NaHCO3 aqueous solution. The organic phase was separated, dried (Na2SO4), filtered and the solvent removed under vacuum. The resulting black oil was purified by flash chromatography on silica gel (Biotage SP4 25M, Cy/EtOAc 95/5) to afford the title compound D47 (0.11 g, 0.69 mmol, 5% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.03 (d, 1H), 7.70 (dd, 1H), 3.92 (s, 3H).

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 75711-01-2, 6-Chloro-5-methoxypyridin-3-amine.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19230-59-2 , The common heterocyclic compound, 19230-59-2, name is 2-Methoxy-3-methylpyridine, molecular formula is C7H9NO, 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.

(lb) 2-Methoxy-3-methyl-5-nitropyridine [Formula 9]; Concentrated sulfuric acid (5 ml) and fuming nitric acid (5 ml) were added to 2-methoxy-3- methylpyridine (1.61 g, 13.1 mmol) under ice cooling, and stirred at 0C for 1 hour and further stirred at room temperature overnight. The reaction mixture was poured onto ice, neutralized with ammonia solution, extracted with ethyl acetate, dried over magnesium sulfate, the solvent was evaporated, thereby yielding the title compound (1.63 g, 9.71 mmol, and 74%). ¹H NMR(400MHz, DMSO-d6) 8 ppm; 2.25(3H, s), 4.04(3H, s), 8.37-8.40(lH, m), 8.92-8.95 (1H, m).

The synthetic route of 19230-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); 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. 4966-90-9, name is 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one, molecular formula is C6H6N2O4, 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. Recommanded Product: 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one

Part A A mixture of 6-methyl-3-nitropyridine-2,4-diol (50 g, 0.29 mol) and phosphorus oxychloride (500 mL) was heated at 90 C. overnight. The excess phosphorus oxychloride was removed under reduced pressure. The resulting black oil was poured into water (1.8 L) and ice. This mixture was extracted with chloroform (*8, 3 L total) and filtered to remove black particulates and break up an emulsion. The combined organics were washed with 10% sodium carbonate (*2) and brine, dried and then concentrated under reduced pressure to provide 52 g of an amber oil. This oil was recrystallized from heptane (115 mL) to provide 43.5 g of 2,4-dichloro-6-methyl-3-nitropyridine as large amber crystals.

With the rapid development of chemical substances, we look forward to future research findings about 4966-90-9.

Reference:
Patent; 3M Innovative Properties Company; US6545017; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 186413-75-2, Adding some certain compound to certain chemical reactions, such as: 186413-75-2, name is 3-Bromo-6-chloro-2-methyl-5-nitropyridine,molecular formula is C6H4BrClN2O2, 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 186413-75-2.

Intermediate 4: S-Bromo-l-chloro–methyl-pyridin-S-ylamine In a 250ml RB flask, 3-bromo-6-chloro-2-methyl-5-nitropyridine (1.5 g, 5.97 mmol, commerical) was dissolved in ethyl acetate (20 mL). To this solution, ammonium chloride (3.19 g, 59.65 mmol) dissolved in water (10ml) was added and stirred at RT for 10 minutes. Then zinc powder (2.340 g, 35.79 mmol) was added at once and the resulting reaction mixture was refluxed at 550C for 6hrs. The reaction mixture was filtered through ceilite and concentrated in vacuo. The residue was partitioned between ethyl acetate (150ml) and water (75). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified by Flash column chromatography using Argonaut purification system, which was eluted with 12% ethyl acetate in hexane to give 5-bromo-2-chloro-6-methylpyridin-3-amine (0.500 g, 37.8 %) as white solid. MS (ES+): 222 for C6H6BrClN2

According to the analysis of related databases, 186413-75-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84199-61-1, 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.84199-61-1, name is 3-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.

4.2. Synthesis of compounds with formula 6: Reaction 1, 2, 4 and 5 of Scheme 1 The first step was made according to the following literature: M. Tiano, P. Belmont J. Organic Chem. 2008, 73, 4101-4109. The second step was carried out according to N. Nishiwaki, S. Minakata, M. Komatsu, Y. Ohshiro, Synlett 1990, 5, 273-275. Synthesis of 7-phenylquinolin-5-ol (6.1) for Example 12.7 6.1Step 1 (= reaction 1): 66 mg 3-Acetyl-2-bromopyridine, 56 mu?, phenylacetylene, 170 mu?, DIPEA, 22.5 mg triphenylphosphinpalladium(II) chlorid, 3 mg Cu(I)I were suspended in 1 mL DMF under argon atmosphere and stirred for 16 h at 25C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and brine. The organic phase was concentrated and the mixture separated via flash chromatography (10 g Si02, cyclohexane cyclohexane /ethylacetate 70:30) to yield 40 mg l-(2-(phenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS : Rt = 1.21 min (method E), M+H = 222.

Statistics shows that 84199-61-1 is playing an increasingly important role. we look forward to future research findings about 3-Acetyl-2-bromopyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; MCCARTHY, Clive; SCOTT, John; WO2013/14060; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1097264-90-8, 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.1097264-90-8, name is 5-Fluoro-3-methoxypyridin-2-amine, molecular formula is C6H7FN2O, molecular weight is 142.13, as common compound, the synthetic route is as follows.

To a solution of 1,1-dimethylethyl (2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.19 g, 0.60 mmol) in DMF (1 ml), 5-fluoro-3-(methyloxy)-2-pyridinamine D48 (0.071 g, 0.50 mmol) was added and the mixture stirred at 80 C. for 2 h. The reaction mixture was eluted through a SCX column. Collected fractions gave 0.14 g of a crude oil containing a mixture of the title compound, the corresponding N-Boc protected derivative and some residual 5-fluoro-3-(methyloxy)-2-pyridinamine. The material was used in the next step without further purification. [N-Boc derivative data. MS: (ES/+) m/z: 364 (M+1). C19H26FN3O3 requires 363]. The crude (0.14 g) was dissolved in DCM (2 ml) and TFA (0.40 ml) was added at 0 C. The reaction was left under stirring for 1 h, then volatiles were removed under vacuum and the residue eluted through a SCX column. Collected fractions gave an oil (0.13 g) containing the title compound D49. The material was used in the next step without further purification. UPLC: rt=0.33 min, peak observed: 264 (M+1). C14H18FN3O requires 263.

Statistics shows that 1097264-90-8 is playing an increasingly important role. we look forward to future research findings about 5-Fluoro-3-methoxypyridin-2-amine.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77837-09-3, 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.77837-09-3, name is Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate, molecular formula is C13H11NO3, molecular weight is 229.23, as common compound, the synthetic route is as follows.

Step 3; 6-Oxo-l -phenyl- 1 ,6-dihydropyridine-3-carboxylic acid:; Lithium hydroxide monohydrate (0.366 g, 8.73 mmol) was added to a mixture of methyl-6-oxo-l -phenyl- 1,6- dihydropyridine-3-carboxylate (1.0 g, 4.37 mmol), tetrahydrofuran (9 mL) and water (6 mL) at 0 C. The mixture was stirred for 1 hour, diluted with water and washed with ethyl acetate. The pH of the aqueous layer was adjusted to 2 using 2 N hydrochloric acid and the precipitate was filtered to give the title compound as a brown solid (0.740 g, 79%). m.p. 256-263 C; *H NMR (400 MHz, DMSO-d6) delta 6.53 (d, / = 9.4 Hz, 1H), 7.40-7.49 (m, 5H), 7.87 (dd, / = 2.5, 9.8 Hz , 1H), 8.23 (d, / = 2.5 Hz, 1H); IR (KBr) upsilon 3446, 1708, 1645, 1577, 1263, 1228 cm”1; MS 214 (M – 1).

The chemical industry reduces the impact on the environment during synthesis 77837-09-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; SOMMERS, Andreas; WO2012/122165; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 67625-38-1, 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. 67625-38-1, name is Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

EXAMPLE 3 6-Chloro-N-(pyrazin-2-yl)imidazo[1,2-a]pyridine-2-carboxamide (No. 3 of the Table)400 mul of a 2M solution of trimethylaluminium in toluene are added dropwise to a solution, cooled to 0 C., of 120 mg of ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate and 61 mg of pyrazin-2-ylamine in 1.2 ml of toluene. The reaction mixture is heated at 70 C. for 16 hours. After evaporating the toluene, the residue is taken up in 0.1N hydrochloric acid and extracted with ethyl acetate. The combined organic phases are washed with aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue is triturated with ethyl ether to give 115 mg of 6-chloro-N-(pyrazin-2-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67625-38-1, Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS; US2010/317673; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem