Tag: M.W:200-300

Electric Literature of 116986-09-5 ,Some common heterocyclic compound, 116986-09-5, molecular formula is C8H8BrNO2, 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.

A mixture of 2-hydroxyl-5-methoxybenzaldehyde (leq) and methyl 3-(bromomethyl)picolinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (1.2eq) was added to this mixture and the reaction was stirred at room temperature for 8-10 hours. The solvent was then evaporated and the reaction mixture extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using S1O2 column chromatography and eluted with the solvent system EtOAc: hexanes = 3:2 to obtain pure product as pale yellow powder with a yield of 82%. IR (Diamond, cm-1): 2897, 1712, 1671, 1607, 1567, 1490, 1445, 1398, 1365, 1275, 1232, 1 165, 1 139, 1 106; 1H-NMR (400 MHz, DMSO-d6): d 10.35 (s, 1H), 8.65 (dd, J = 4.6, 1.28 Hz, 1H), 8.2 (dd, J = 7.84, 0.76 Hz, 1H), 7.66 (dd, J= 7.88, 4.68 Hz, 1H), 7.24 (m, 3H), 5.49 (s, 2H), 3.83 (s, 3H), 3.77(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 188.81, 166.12, 154.66, 153.55, 148.49, 146.69, 136.89, 133.04, 126.43, 124.89, 122.96, 1 15.79, 1 10.68, 67.44, 55.56, 52.34. MS (ESI) m/z found 324.08 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 98% pure.

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. 116986-09-5, Methyl 3-(bromomethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); 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. 623585-74-0, name is Methyl 2,5-dichloroisonicotinate. A new synthetic method of this compound is introduced below., Quality Control of Methyl 2,5-dichloroisonicotinate

To a cold solution of methyl 2,5-dichloroisonicotinate (500 mg, 2.42 mmol) in THF (15 mL) was added N-Methyl-2-pyrrolidone (1.4 mL), iron(III)acetyl acetone (43 mg, 0.12 mmol) and methyl magnesium bromide (36 mg, 0.305 mmol) at 0C. The reaction mixture was stirred at 0C for 1 h and then at rt for 18 h. The reaction mixture was quenched with brine and was extracted with ethyl acetate. The organic layer was separated, dried, filtered and concentrated to afford 130 mg of the title product.1H NMR (300 MHz, DMSO d6): delta 8.46 (s, 1H), 7.74 (s,lH), 3.87 (s, 3H), 2.44 (s, 3H).

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, 623585-74-0, Methyl 2,5-dichloroisonicotinate.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/72825; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, Adding some certain compound to certain chemical reactions, such as: 73112-16-0, name is 2,6-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 73112-16-0.

(Synthesis of aromatic compound P2)Aromatic compound P2 was synthesized according to the following reaction formula. [Chemical Formula 119]Aromatic compound P2[0139] First, compound 2(l,4-bis-(2-bromo-4-methylpyridm-6-yl)-3,4-diaminobenzene) to be used as the starting material was synthesized via 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole.[0140] Specifically, 4.930 g of 2,6-dibromo-4-methylpyridine (0.0196 mol) and 0.762 g of 4,7-bis-pinacolato-diborane-2,l ,3-benzothiadiazole (0.00196 mol) were dissolved in 120 ml of toluene to obtain a toluene solution. To the toluene solution there were added 10 ml of an aqueous solution dissolving 10 g of K2C03, and 0.032 g of trioctylmethylammonium chloride (trade name: Aliquat336 by Aldrich Co., hereunder referred to as “Aliquat336”). After deaerating the solution with argon, 0.1132 g of tetrakis-(triphenylphosphin)-Pd(0)(0.098 mmol) was added and the mixture was heated at 80C for 1 week. This was followed by column purification (dichloromethane/hexane/ethyl acetate) to obtain 0.507 g of 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole at a yield of 54% .Results of NMR analysis and MS analysis of 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole-NMR (250 MHz, CD2C12): delta = 8.684 ppm (s, 2H); 8.625 ppm (s, 2H); 7.385 ppm (s, 2H); 2.484 ppm (s, 6H)MS(FD, 8 kV) Found: m/z 476.2 (M ), Calculated: m/z: 476.19 (M+)

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. 73112-16-0, 2,6-Dibromo-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Max Planck Gesellschaft zur Foerderung der Wissenschaften e. V.; KOSHINO, Nobuyoshi; HIGASHIMURA, Hideyuki; MUELLEN, Klaus; MALOTKI, Christian von; SU, Qi; BAUMGARTEN, Martin; NOROUZI-ARASI, Hassan; ARNOLD, Lena; LIU, Ruili; WO2011/52805; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a solution of sodium hydride [(1 .52 g, 63.17 mmol (95%)] in DMSO (20.0 mL) at 0 00 diethylmalonate (10.11 g, 63.17 mmol) was added and kept for reflux at 100 00 forlh. The reaction mixture was cooled to room temperature and intermediate 32b(10.0 g, 42.11 mmol) was added drop wise in DMSO (20 mL) to the resulting solutionand refluxed at 10000 for 3 h. The reaction mixture was quenched with ice water and extracted by using Ethyl acetate washed with water, and dried over anhydrous Na2SO4 The solvent was removed under vacuo to yield the title compound (10.0 g, 75.00%) as a brown oily product. LOMS: (M-H) = 315.0

The synthetic route of 75806-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 885168-04-7, 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 885168-04-7, name is 5-Bromo-3-chloropicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Conc. sulfuric acid (5.0 mL) was added to an ice-cold (0C) mixture of 5-bromo-3-chloropicolinaldehyde(5 g, 22.7 mmol, 1 eq) and 3-butene-1-ol (4.1 mL, 45.5 mmol, 2 eq) and the mixture was stirred for 16 h at RT. The reaction mass was poured into crushed ice, neutralized by addition of solid NaHCO3, extracted with EtOAc (2×1 00 mL) and the organic layer was washed with brine (150 ml). Combined organic layer was dried over anhydr. Na2SO4, filtered and the solvent was evaporated under reduced pressure to get crude mass which was then purified by combiflash CC to afford 2-(5-bromo-3-chloropyridin-2-yl)tetra-hydro-2H-pyran-4-ol (1.1 g, 17%) as colorless oil.

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 885168-04-7, 5-Bromo-3-chloropicolinaldehyde.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-88-9 , The common heterocyclic compound, 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine, molecular formula is C6H5ClIN, 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.

The mixture of 1.0 g of 2-chloro-4-iodo picoline, 84 mg of palladium acetate, 218 mg of 1,1′-bisdiphenylphosphino ferrocene, 990 mg of sodium hydrogen carbonate, 10 mL of N,N-dimethylformamide, and 10 ml of methanol, was stirred overnight in a carbon monoxide atmosphere at 80C. After cooling the reaction mixture back to room temperature, water and a saturated aqueous solution of sodium hydrogen carbonate were added thereto, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 522 mg of 2-chloro-3-methylisonicotinic acid methyl ester [48-1] as a colorless oily product.

The synthetic route of 153034-88-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1790650; (2007); 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. 878197-68-3, name is 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 878197-68-3

To a solution of Lambda/-methyl-5,6,7,8-tetrahydro-8-quinolinamine (500 mg, 3.1 mmol) and 5-bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (770 mg, 3.4 mmol) in dichloroethane (17 ml_) was added acetic acid (180 mul_, 3.1 mmol) and sodium triacetoxyborohydride (2.0 g, 9.3 mmol). The mixture was stirred at room temperature for 15 hours and then filtered through a silica plug and rinsed with 10% ammonium hydroxide- acetonitrile. The solvent was removed and the residue diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, and dried with magnesium sulfate to give 1.1 g (99% yield) of Lambda/-[(5-bromoimidazo[1 ,2-a]pyridin-2-yl)methyl]-Lambda/- methyl-5,6,7,8-tetrahydro-8-quinolinamine as an orange oil. 1H-NMR (CDCI3): delta 8.50 (d, 1H), 7.92 (s, 1 H), 7.49 (d, 1 H), 7.32 (d, 1 H), 7.03 (m, 2H), 6.96 (m, 1H), 4.09 (m, 1 H), 3.94 (s, 2H), 2.72 (m, 2H), 2.40 (s, 3H), 2.12 (m, 1H), 1.99 (m, 2H), 1.68 (m, 1H); MS m/z 372 (M+1).

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, 878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/26703; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 880870-13-3 ,Some common heterocyclic compound, 880870-13-3, molecular formula is C6H5BrClNO, 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: Preparation of l-(4-(6-chloro-4-methoxypyri din-3 -yl)phenyl)pyrrolidin-2-one. [0794] A mixture of l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin- 2-one (500 mg, 1.74 mmol), 5-bromo-2-chloro-4-methoxypyridine (387 mg, 1.74 mmol), Pd(dppf)Cl2 (127 mg, 0.174 mmol) and Na2C03 (554 mg, 5.22 mmol) in dioxane (6 mL) and water (1.5 mL) was degassed and purged w ith N2 for 3 times. And the resulting reaction mixture was stirred at 100 C for 2 hours under N2 atmosphere. A black suspension was formed. LCMS showed the purity of the desired product is 51% (Rt = 0.649 min; MS Calcd: 302.1; MS Found: 302.8 [M+H]+). The reaction mixture was diluted with water (10 mL). The aqueous layer was extracted with EtOAc (30 mL x3). The combined organic layer was washed with water (20 mL x2), brine (40 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by Combi Flash (20% to 60% EtOAc in PE) to give 1-(4- (6-chloro-4-methoxypyridin-3-yl)phenyl)pyrrolidin-2-one (450 mg, yield: 78%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; KESICKI, Edward A.; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (450 pag.)WO2019/126731; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 186203-81-6, tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of tert-but l hexahydro- l H-pyrrolo[3,4-b]pyridine-6(2H)- carboxylate (1.60 g), l -bromo-3-chloropropane (1.50 mL) and 2C03 (3.00 g) in acetone was heated to reflux for 9 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 1 : 1 (v/v) PE/EA) to give the title compound as yellow oil (0.53 g, 65.00 %), HPLC: 89.00 %. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 303.2 (M+l ).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,186203-81-6, tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Jiancun; ZHANG, Yingjun; ZHANG, Weihong; LIU, Bing; ZHANG, Jiquan; LIU, Jinlei; ZHANG, Lu; WO2013/71697; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884494-51-3, 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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid, molecular formula is C6H3FINO2, 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.

Step 1 : Methyl 2-(((3R.6R)-l-(ter?-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4- iodonicotinate A solution of 2-fluoro-4-iodonicotinic acid (4.43 g, 16.61 mmol) in DMSO (75 ml) was treated with sodium hydride (0.471 g, 19.62 mmol) in portions. After stirring a few minutes, (2R,5R)-tert-butyl 5-hydroxy-2-methylpiperidine-l-carboxylate (8, 3.25 g, 15.10 mmol) was added. Additional sodium hydride (0.362 g, 15.10 mmol) was added in portions and, after stirring for a few minutes, the reaction was heated at 40 C for 2 days. The reaction was cooled and quenched with saturated, aqu. NH4C1, then rapidly diluted with H2O and EtOAc. Cone. HCl was added until the the solution was acidic, then rapidly extracted 3x with EtOAc. The organics were washed 2x with H20, lx with brine, dried over MgS04, filtered, concentrated, and dried to provide the crude carboxylic acid. The crude foam was dissolved in DMF (76 mL) and cooled at 0 C and treated with sodium hydride (0.55 g, 23 mmol) in portions. After stirring ~10 mins, iodomethane (1.34 mL, 21.4 mmol) was added and the reaction was warmed to RT overnight. The reaction was cooled at 0 C and quenched by additon of saturated, aqu. NH4C1 and stirred well. Saturated, aqu. aHC03 was added and the reaction was extracted 2x with EtOAc. The organic fractions were washed with brine, dried over MgS04, filtered, and concentrated to provide the title compound as a crude oil. LRMS m/z (M+H) 477.3 found, 477.1 required.

According to the analysis of related databases, 884494-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/62533; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem