Month: March 2022

Related Products of 727356-19-6, 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.727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine, molecular formula is C6H5BrClN, molecular weight is 206.47, as common compound, the synthetic route is as follows.

To a solution of (4-fluoro-phenyl)-carbamic acid terf-butyl ester (60144-53-8, 750 mg, 3.55 mmol) in tetrahydrofuran (10 mL) was added sodium hydride (60% dispersion in mineral oil, 150 mg, 3.9 mmol). After 30 minutes, tetra-n-butylammonium iodide (51 mg, 0.36 mmol) and 2-bromo-6-chloromethyl-pyridine (804 mg, 3.9 mmol) was added to the reaction and the mixture was heated to 70C. After 1 hour, the reaction was cooled to room temperature, quenched with saturated sodium bicarbonate (10 ml.) and extracted with ethyl acetate (2 x 15 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (silica gel; 10% ethyl acetate in hexanes) provided (6-bromo-pyridin-2-ylmethyl)-(4-fluoro-phenyl)-carbamic acid te/t-butyl ester (700 mg, 1.84 mmol) as an oil which solidified upon standing.

Statistics shows that 727356-19-6 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-6-(chloromethyl)pyridine.

Reference:
Patent; WYETH; WO2008/73934; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 727356-19-6, 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.727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine, molecular formula is C6H5BrClN, molecular weight is 206.47, as common compound, the synthetic route is as follows.

Step 3; Preparation of trans-4-{[5-(6-bromopyridin-2-yl)thiazol-2-ylamino]methyl}cyclohexanecarboxylic acid methyl ester A solution of trans-4-thiouredide methylcyclohexane carboxylic acid methyl ester (1.55 g, 6.73 mmol) obtained in Step 2,2-bromo-6-chloromethylpyridine (1.38 g, 6.73 mmol) obtained in Step 1 of Example 1 in ethanol (15 ml) was stirred under refluxing for 4 hours. After the reaction solution was cooled to room temperature, N,N-dimethylformamide dimethylacetal (0.9 ml, 10 mmol), triethylamine (1.8 ml, 20 mmol) were added and the mixture was stirred under refluxing for 1 hour. The reaction solution was cooled to room temperature and the solid obtained by vacuum concentration was collected by filtration. trans-4-{[5-(6-bromopyridin-2-yl)thiazol-2-ylamino]methyl}cyclohexanecarboxylic acid methyl ester (2.02 g, 73%) was obtained by sequentially washing with water (10 ml), diethyl ether (10 ml) and drying in vacuo. 1H-NMR (400 MHz, DMSO-d6) delta: 8.15(1H,t,J=5.7 Hz), 7.83(1H,s), 7.74(1H,d,J=7.9 Hz), 7.63(1H,t,J=7.9 Hz), 7.31(1H,d,J=7.9 Hz), 3.15-3.06(2H,m), 2.32-2.19(1H,m), 1.97-1.87(2H,m), 1.85-1.76(2H,m), 1.63-1.49(1H,m), 1.37-1.23(2H,m), 1.06-0.93(2H,m).

The chemical industry reduces the impact on the environment during synthesis 727356-19-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; JAPAN TOBACCO INC.; US2006/205731; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 372198-69-1 , The common heterocyclic compound, 372198-69-1, name is Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate, molecular formula is C10H9BrN2O2, 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.

[002981 Example 4[00299] Preparation of compound 8:[00300] 1. Anethanol solution of compound 5 (12400 g in 51 L of ethanol) was added to an appropriately sized stainless steel reactor at room temperature under nitrogen atmosphere.[00301] 2. Compound 6 (9500 g) was added as a solid in one portion at room temperature.[00302] 3. The reaction mixture was heated to reflux (~78C) and stirred for 1-2 days.[00303] 4. The reaction was monitored by HPLC.[00304] 5. Upon completion, the reaction mixture was allowed to cool to room temperature.[00305] 6. NaOH solution (9884 g solid pellets dissolved in 38 L of water) was added as a stream over a30 min period at an internal temperature below 35 C.[00306] 7. The reaction mixture was heated to reflux (~78C) for 3 to 4 hours.[00307] 8. The reaction was monitored by HPLC.[00308] 9. Upon completion, the reaction mixture was cooled to an appropriate temperature to start solvent removal.[00309] 10. All ethanol (approximately 5 volumes of ethanol) was removed under vacuum at 40 to 45 C.[00310] 11. The reaction mixture was cooled to room temperature.[00311] 12. Water (57 L; 6 vol) was added at room temperature.[00312] 13. The aqueous solution was washed with ethyl acetate (2 x 38 L) to remove all organic impurities.[00313] 14. The lower aqueous layer was cooled to 0-5 C and acidified with cone. HCl (~15 L) until reaching pH 1-2.[00314] 15. The reaction mixture was stirred for 1 to 2 hours at 0 to 5 C.[00315] 16. The mixturewas filtered and the cake was washed with water (2 x 38 L) and acetone (2 x 19L) followed by drying for 1-2 hours.[00316] 17. The solid collectedwas transferred back into an appropriately sized reactor.[00317] 18. Heptane (95 L; 10 vol) was addedto the reactor; the suspension was stirred for 4 to 5 hours at roomtemperature.[00318] 19. The solidwas collected by filtration and washed with heptane (2 x 19 L).[00319] 20. The solid (15 kg) was suspended in methanol (75 L; 5 vol) at room temperature for 2 hours.[00320] 21. The suspension was filtered and the solid collected was washed with methanol (2x 5L).22. The solid was dried under vacuum at 50C to constant weight to give compound 8 as an off-white to white solid (10169 g, 83.3 % yield; HPLC purity 99.2%;1HNMR (DMSO-d6, 300 MHz) ? 9.4 (s, 1H), 8.3(s, 1H), 7.85-7.67 (m, 2H)).

The synthetic route of 372198-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INTELLIKINE, LLC; MARTIN, Michael; WORRALL, Christopher, Peter; GANCEDO, Susanna, Del Rio; REN, Pingda; WO2013/71272; (2013); A1;,
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 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H3ClN2

(E)-N-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(3-hydroxyphenyl)-2-methylacrylamide (1.0 g, 2.81 mmol), 4-chloropicolinonitrile (428 mg, 3.09 mmol) and cesium carbonate (2.75 g, 8.43 mmol) were combined and stirred in DMF. The reaction mixture was heated at 100 C. overnight and then cooled to rt. The mixture was filtered to remove cesium carbonate, the collected precipitate was washed with EtOAc, and the combined filtrate was concentrated. Purification by column chromatography (SiO2, 0-80% EtOAc in hexanes) provided the title compound (883 mg). LCMS, FA: Rt=2.15 min, [MH+ 458.0].

With the rapid development of chemical substances, we look forward to future research findings about 19235-89-3.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2006/160803; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic 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, name: Imidazo[1,2-a]pyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. name: Imidazo[1,2-a]pyridine-2-carboxylic acid

Working Example 47 To a mixture of 3-methoxymethyl-1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (500 mg) obtained in Reference Example 14, imidazo[1,2-a]pyridine-2-carboxylic acid (211 mg), triethylamine (657 mg) and N,N-dimethylformamide (3 ml) is added dropwise under ice-cooling, while stirring, a solution of diethyl cyanophosphonate (277 mg) in N,N-dimethylformamide (1 ml), and the mixture is stirred for one hour. The reaction mixture is poured into ice-water and extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent: ethyl acetate), followed by recrystallization to give 2-[2-methoxymethyl-4-(3,4,5-trimethoxybenzyl)piperazin-1-ylcarbonyl]imidazo[1,2-a]-pyridine as colorless prisms (354 mg), m.p. 129-130C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP368670; (1990); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 84539-34-4, name is 4-Amino-3,5-dibromopyridine. A new synthetic method of this compound is introduced below., Safety of 4-Amino-3,5-dibromopyridine

3-Bromo-5-(2-fluoro-4-trifluoromethyl-phenyl)-pyridin-4-ylamine (Intermediate compound 10) To a solution of commercially available 4-amino-3,5-dibromopyridine (1.000 g, 3.9697 mmol) in DME (25 ml) and water (12 ml), 2-fluoro-4- (thfluoromethyl)phenylboronic acid (0.908 g, 4.3667 mmol) and sodium carbonate (0.841 g, 7.9394 mmol) were added. The reaction mixture was degassed and kept 5 under nitrogen atmosphere during the entire course of the reaction. Palladium (II) (bistriphenylphosphine)dichloride (0.139 g, 0.1985 mmol) was added and the resulting reaction mixture, heated at 9O0C for 2 hours, was worked up by addition of water and extraction with AcOEt. The organic phase, dried over anhydrous MgSO4, afforded upon evaporation a yellow gummy residue (~1.3 g), which eluted through silica gel with 10 15% AcOEt in hexane gave 0.520 g (-39% yield) of the pure title compound as a white 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, 84539-34-4, 4-Amino-3,5-dibromopyridine.

Reference:
Patent; NEUROSEARCH A/S; WO2009/112461; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 13269-19-7, name is 2-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below., Quality Control of 2-Nitropyridin-3-amine

To a stirred suspension of 2-nitro-pyridin-3-ylamine (25.0 g, 179.7 mmol) andsodium acetate (15.5 g, 188.7 mmol) in acetic acid (150 mL), a solution of bromine (13.8 mL, 269.6 mmol) in acetic acid (50 ml) was added dropwise and the reaction mixture was stirred overnight. The acetic acid was removed under reduced pressure. The residue wascooled to 0C, neutralized with saturated sodium bicarbonate solution to adjust the pH to-7, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Theresidue was triturated with ethyl acetate to afford compound (34.4 g, 88% yield) as a

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, 13269-19-7, 2-Nitropyridin-3-amine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; (90 pag.)WO2019/3143; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 56673-34-8, 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.56673-34-8, name is 3-Bromo-6-mercaptopyridine, molecular formula is C5H4BrNS, molecular weight is 190.06, as common compound, the synthetic route is as follows.

Weigh 0.591 g of Nd (OTf) 3, 0.33 g of tetraacetylated fucose,0.19 g of 5-bromo-2-mercaptopyridine in a parallel reaction tube. Nitrogen atmosphere were added 10mL1,2-dichloroethane, ionic liquid PFIL-2 [R1, R2, R3 = phenyl,n = 4, X = (CF3SO2) 2N] 0.5mL, the reaction tube was sealed, the reaction was stirred,Microwave irradiation using intermittent, power 500W,Each irradiation for 5 minutes, stop irradiation for 1 minute. Reaction for 5 hours,Temperature control at 80 degrees Celsius. The reaction was terminated by adding water.Separation by silica gel column gave 0.336 g of glycoside 1 in 73% yield.Ionic liquids can be reused, no significant change in yield.

Statistics shows that 56673-34-8 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-6-mercaptopyridine.

Reference:
Patent; Ningbo University; Chen Weiting; (9 pag.)CN106397507; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 639091-75-1, Adding some certain compound to certain chemical reactions, such as: 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate,molecular formula is C12H16N2O4, 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 639091-75-1.

Compound 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaC12 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight at ambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20mL of NaC1 (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

According to the analysis of related databases, 639091-75-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PIERRE FABRE MEDICAMENT; JOUHANNEAUD, Alexandra; GOETSCH, Liliane; BROUSSAS, Matthieu; BEAU-LARVOR, Charlotte; CHAMPION, Thierry; ROBERT, Alain; HAEUW, Jean-Francois; RILATT, Ian; PEREZ, Michel; (244 pag.)WO2017/72196; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1231930-13-4 ,Some common heterocyclic compound, 1231930-13-4, molecular formula is C6H5BrN2O2, 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.

3-bromo-2-methyl-6-nitropyridine (2.2 g, 10.1 mmol), bis(pinacolato)diboron 1.3.0 g, 12.1 mmol), Pd(dppf)Cl2 (200 mg), and potassium acetate (3.0 g, 30.4 mmol) were dissolved in 1,4-dioxane (40 mL). The reaction solution was stirred at 110 C. for 2 hrs under nitrogen protection. When the LCMS showed that the reaction completed, the reaction solution was filtered through celite, and the filtrate is concentrated to dryness. The residue was separated by a rapid silica gel column (020% EA:PE) to obtain 2-methyl-6-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.8 g, yield 67%), which was directly used in the next reaction.

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. 1231930-13-4, 3-Bromo-2-methyl-6-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Abbisko Therapeutics Co., Ltd.; ZHAO, Baowei; ZHANG, Mingming; YU, Hongping; YANG, Shuqun; CHEN, Zhui; XU, Yaochang; US2020/71302; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem