Month: July 2021

Reference of 6188-23-4 , The common heterocyclic compound, 6188-23-4, name is 6-Bromoimidazo[1,2-a]pyridine, molecular formula is C7H5BrN2, 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: 1 To a solution of 6-bromoimidazo [l ,2-a]pyridine (20 g, 101.5 mmol) in ACN (300 mL) was added N-iodosuccinimide (22.8 g, 101.5 mmol) at rt and stirred for 5 h. The reaction mixture was filtered and washed with hot acetonitrile to afford 6-bromo-3-iodoimidazo[l,2- ajpyridine (22 g, 67%) as a pale yellow solid. 1H NMR (400 MHz, CDC13) delta 8.29 (s, 1H), 7.58 (d, J= 9.2 Hz, 1H), 7.35 (d, J= 7.6 Hz, 1H), 7.27 (s, 1H).

The synthetic route of 6188-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1149-23-1, 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 1149-23-1, name is Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To the solution of HEH or BNAH (0.1 mmol) in ethanol or acetonitrile (2 mL) wasadded polysulfide 1 (0.2 mmol). The solution was incubated at r.t. or 37 C for 20 h(for HEH) or 5 h (for BNAH) under dark. After removing the solvent under reducedpressure, the yield of product 2 or 3 were determined by 1H-NMR.

According to the analysis of related databases, 1149-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Peng, Bo; Liu, Chunrong; Li, Zhen; Day, Jacob J.; Lu, Yun; Lefer, David J.; Xian, Ming; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 542 – 545;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1824-81-3, 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. 1824-81-3, name is 2-Amino-6-picoline. A new synthetic method of this compound is introduced below.

2. Dissolve 10.80 g of 2-amino-6-methylpyridine (Compound 9) in 500 mL of acetonitrile, add 33.7 g of N-iodosuccinimide, and react at room temperature for 3 h. The precipitate was filtered, washed with 200 mL of cold acetonitrile, and dried under vacuum to obtain 12.2 g (compound 10) as an off-white solid with a yield of about 52%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1824-81-3, 2-Amino-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; China Agricultural University; Wang Zhanhui; Shen Jianzhong; Wen Kai; Li Chenglong; Yu Xuezhi; Zhang Suxia; Shi Weimin; Yu Wenbo; (19 pag.)CN110713457; (2020); A;,
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. 1136-52-3, name is (2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol. A new synthetic method of this compound is introduced below., Recommanded Product: 1136-52-3

General procedure: A mixture of alpha4,3-O-isopropylidene pyridoxine, the respective saccharide and molecular sieves (4 A) was stirred under argon atmosphere in dry dichloromethane (5 mL) at rt for 1 h before it was cooled to 0 C. Silver triflate and N-iodosuccinimide (3.0 eq.) were added and the reaction mixture allowed to reach rt overnight. The mixture was diluted with dichloromethane (10 mL) and filtered through a pad of celite. Afterwards, the filtrate was washed with Na2S2O3 (10 % in water, 30 mL) and the aqueous phase was extracted with dichloromethane (3 x 40 mL). The combined organic layers were washed with distilled water (1 x 50 mL), brine (1 x 50 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product subjected to column chromatography using SiO2 (pentane/ethyl acetate 1/1 to 1/4, gradient elution) followed by C18 (methanol, isocratic) to afford the glycoside, which was used directly in the deprotection reaction.

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, 1136-52-3, (2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol.

Reference:
Article; Bachmann, Thomas; Schnurr, Christian; Zainer, Laura; Rychlik, Michael; Carbohydrate Research; vol. 489; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6188-25-6, 6-Chloroimidazo[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, Safety of 6-Chloroimidazo[1,2-a]pyridine, blongs to pyridine-derivatives compound. Safety of 6-Chloroimidazo[1,2-a]pyridine

(ii) The whole amount of 7beta-[2-(2-amino-5-chlorothiazol-4-yl)-2(Z)-(carboxymethoxyimino)acetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid, 2.5 g of 6-chloroimidazo[1,2-a]pyridine and 2 g of sodium iodide are mixed in 20 ml of 50% acetonitrile in water and the mixture is heated at 70 C. for 90 minutes with stirring, and then cooled to room temperature. Two grams of sodium bicarbonate is added to the reaction mixture and the mixture is chromatographed on a column of silica gel (50 g). The column is washed with 0.3 l of acetone and then with 0.5 l of acetone_water=8:1 and the product is then eluted with acetone_water=5:2. Fractions containing the objective compound are concentrated and the residue is placed on a column of Sephadex LH-20 (Pharmacia Inc., Sweden) and eluted with water. Fractions containing the objective compound are lyophilized to give the above-identified compound. Elemental analysis for C22 H16 Cl2 N7 NaO7 S2.2H2 O: Calcd.(%): C, 38.60; H, 2.95; N, 14.33. Found (%): C, 38.40; H, 2.99; N, 14.06. IR spectrum numaxKBr cm-1: 1770, 1680, 1620, 1520, 1440, 1320. NMR spectrum (d6 -DMSO)delta: 2.04 and 3.40(2H, ABq, J=18 Hz), 4.25(2H, br.s), 4.97(1H, d, J=5 Hz), 5.40(2H, br.s), 5.66(1H, d. d, J=5 Hz and 8 Hz), 7.31(2H, br.s), 8.05(1H, d, J=6 Hz), 8.40(1H, d, J=3 Hz), 8.58(1H, d, J=7 Hz), 9.28(1H, br. s), 9.77(1H, d, J=6 Hz).

The synthetic route of 6188-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4788185; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18820-82-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 18820-82-1 as follows.

A mixture containing 5 mL water and PdCl2 (0.4800 g,2.71 mmol) was added into a 10 mL methanol solution of Na2mnt(1.8600 g, 9.99 mmol). This mixture was stirred and refluxed forone hour, and then a 20 mL water solution of N-hydrogenpyridiniumbromide (3.3200 g, 20.70 mmol) was added into there fluxed reactants in drops, over which time a sediment appeared. Deep orange microcrystals were obtained after recrystallization of the sediment from diethyl ether (yield: 78%, based on PdCl2). IR(cm1): 3060(s), 3030(s), 1990(w), 1940(w), 1870(w), 1450(s),1150(s), 1070(s), 764(s). Elemental anal. Calcd for C18H12N6PdS4(FW 547.008): C: 39.52%; H, 2.21%; N, 15.36%; Pd, 19.45%. Found: C,39.80; H, 2.53; N, 15.01; Pd,19.93%. 13C NMR (600 MHz, DMSO e d6)d (ppm): 155.3, 139.5, 125.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18820-82-1, its application will become more common.

Reference:
Article; Qiao, Fang; Wang, Chi-Feng; Chen, Xue-Xue; Wang, Peng; Chi, Yan-Hui; Cottrill, Ethan; Pan, Ning; Shi, Jing-Min; Zhu-Ge, Wei-Wei; Fu, Yong-Xing; Qian, Xiao-Ping; Xu, Jun; Journal of Molecular Structure; vol. 1100; (2015); p. 513 – 517;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 897732-75-1, Adding some certain compound to certain chemical reactions, such as: 897732-75-1, name is 2-Methyl-6-(methylsulfonyl)pyridin-3-amine,molecular formula is C7H10N2O2S, 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 897732-75-1.

Step 1: Acetic acid 6-methanesulfonyl-2-methyl-pyridin-3-yl ester; A solution of boron trifluoride etherate (670 muL, 5.3 mmol) in dimethylformamide (2 mL) was cooled to -15 C. using an ice-acetonitrile bath, and then stirred for 15 min at this temperature. A solution of 6-methanesulfonyl-2-methyl-pyridin-3-ylamine (Intermediate 4; 653 mg, 3.5 mmol) in 1,2-dimethoxyethane (16 mL) was added dropwise to the solution at -15 C. and the stirring was continued for a further 15 min. tert-Butyl nitrite (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 90%; 483 mg, 4.2 mmol) was added dropwise, and the reaction mixture was stirred at -15 C. for 15 min and then at 0 C. for 1 h. Hexane (20 mL) was added and the solid was filtered off and washed with hexane. The solid was added to acetic anhydride (5 g, 49 mmol) and the mixture was heated at 100 C. for 1 h. The acetic anhydride was evaporated under high vacuum and then 1 M aqueous sodium carbonate solution was added. The mixture was extracted three times with dichloromethane. The dichloromethane was evaporated and the residue was purified by silica gel column chromatography, eluting with 0-40% ethyl acetate/hexane to give acetic acid 6-methanesulfonyl-2-methyl-pyridin-3-yl ester (331 mg, 41%) as a solid. 1H NMR (CDCl3) delta 2.39 (s, 3H), 2.52 (s, 3H), 3.22 (s, 3H), 7.62 (d, 1H, J=8.2 Hz), 7.98 (d, 1H, J=8.4 Hz).

According to the analysis of related databases, 897732-75-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Erickson, Shawn David; Gillespie, Paul; Guertin, Kevin Richard; Karnachi, Prabha Saba; Kim, Kyungjin; Ma, Chun; McComas, Warren William; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Tilley, Jefferson Wright; Zhang, Qiang; US2009/286812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1001413-01-9, Adding some certain compound to certain chemical reactions, such as: 1001413-01-9, name is 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid,molecular formula is C13H9F2NO3, 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 1001413-01-9.

Compound 25.5 (0.168 grams, 0.749), l-(3,4-difluoro-benzyl)-2-oxo-l,2-dihydro- pyridine-3-carboxylic acid (0.200 grams, 0.749 mmol), N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (0.172 grams, 0.899 mmol) and 1-hydroxybenzotriazole monohydrate (0.138 grams, 0.899 mmol), and diisopropylethylamine (0.652 ml, 3.75 mmol) were dissolved in dimethylacetamide (4 ml) and stirred at ambient temperature for 17 hours. The reaction was diluted with EtOAc, washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica (3% MeOH/DCM) to yield Compound 25.6 (0.066grams, 0.140 mmol, 19%). ES (+) MS m/e = 472 (M+l). IH NMR (400 MHz, DMSO-d6) delta ppm 4.59 (m, 2 H) 5.20 (m, 2 H) 6.58 (m, 1 H) 7.14 (m, 2 H) 7.40 (m, 2 H) 8.00 (m, 1 H) 8.08 (m, 1 H) 8.22 (m, 1 H) 8.29 (m, 2 H) 8.39 (m, 2 H) 8.84 (m, 1 H) 10.11 (m, 1 H) 12.06 (m, 1 H).

According to the analysis of related databases, 1001413-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNESIS PHARMACEUTICALS; BIOGEN IDEC, INC.; WO2008/5457; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3430-17-9, 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 3430-17-9, name is 2-Bromo-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

[00299] 2-Bromo-3-methylpyridine (1.0 eq) was dissolved in toluene (12 vol). K2C03 ( 4.8 eq)was added, followed by water (3.5 vol). The resulting mixture was heated to 65 oc under astream ofN2 for 1 hour. 3-(t-Butoxycarbonyl)phenylboronic acid (1.05 eq) andPd(dppf)Cb·CH2Cb (0.015 eq) were then added and the mixture was heated to 80 C. After 2hours, the heat was turned off, water was added (3.5 vol), and the layers were allowed toseparate. The organic phase was then washed with water (3.5 vol) and extracted with 10%aqueous methanesulfonic acid (2 eq MsOH, 7.7 vol). The aqueous phase was made basic with50% aqueous NaOH (2 eq) and extracted with EtOAc (8 vol). The organic layer wasconcentrated to afford crude tert-butyl-3-(3-methylpyridin-2-yl)benzoate (82%) that was useddirectly in the next step.

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 3430-17-9, 2-Bromo-3-methylpyridine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VERWIJS, Marinus, Jacobus; KARKARE, Radhika; MOORE, Michael, Douglas; WO2014/71122; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14294-11-2 ,Some common heterocyclic compound, 14294-11-2, molecular formula is C6H7N3S, 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.

Analogously to Example 1, but using pyridyl-thiourea in place of 2-imino-4-thiobiuret, there is obtained ethyl 2-(pyridin-2-ylamino)-thiazole-4-carboxylate; MS: 250 (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,14294-11-2, its application will become more common.

Reference:
Patent; Hoffman-La Roche Inc.; US6100282; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem