Day: August 9, 2021

Electric Literature of 6602-32-0, 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 6602-32-0 as follows.

Synthesis of T131 proceeded from the known intermediate 131-3 (Schlosser, M. et. al. Tetrahedron 2005, 61, 717-725) via the multi-step sequence illustrated. For the key RCM step, either Grubb’s second generation catalyst (Ru-1) or the Grubbs-Hoveyda catalyst (Ru-2) could be employed. The yield for the synthesis of 131-8 was complicated by concurrent elimination side reaction. In order to avoid this, an alternative synthetic route conducting the RCM prior to the displacement reaction can be employed.1H NMR (CDCl3, 300 MHz): delta 7.97 (d, J=4.7, 1H), 6.84 (d, J=5.0, 1H), 5.02 (s, br, 1H), 4.14 (m, 1H), 3.83 (m, 2H), 3.13 (m, 2H), 2.80 (m, 5H), 1.90 (m, 4H), 1.44 (s, 9H)13C NMR (CDCl3, 75 MHz): delta 156.14, 150.12, 149.36, 140.12, 129.59, 122.20, 79.19, 77.20, 65.19, 40.13, 29.42, 28.42, 28.24, 24.06, 22.94MS: 323 (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,6602-32-0, its application will become more common.

Reference:
Patent; Tranzyme Pharma Inc.; US2008/194672; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-78-7, 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. 153034-78-7, name is 2-Fluoro-3-iodo-5-methylpyridine. A new synthetic method of this compound is introduced below.

(2) Synthesis of 2-fluoro-4-iodo-3,5-dimethylpyridine Diisopropylamine (88 mL) was added to THF (1.2 L), and the mixture was cooled to -18 C. in a nitrogen atmosphere. A 2.69 M solution of n-butyllithium in hexane (215 mL) was added dropwise to the solution. After completion of the dropwise addition, the mixture was warmed to -5 C. with stirring over 30 minutes. The reaction mixture was cooled to -72 C. A solution of 2-fluoro-3-iodo-5-methylpyridine (109.69 g) in TIE (240 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -74 C. for 1.5 hours. A solution of methyl iodide (36 mL) in THF (160 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -70 C. to -74 C. for two hours. After completion of the reaction, water (200 mL) was added to the reaction mixture at the same temperature. The mixture was stirred at the same temperature for two minutes. The reaction mixture was returned to room temperature, and water (1.2 L) was then added. The mixed solution was stirred for three minutes. Water (300 mL) was further added. The mixture was extracted with MTBE (1.2 L). The organic layer was washed with brine (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. n-heptane (100 mL) was added to the residue, followed by cooling. The precipitated solid was collected by filtration. The residue was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. This operation was repeated twice to give the title compound (86.9 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.39-2.40 (m, 6H), 7.80-7.82 (m, 1H). ESI-MS m/z 252 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-78-7, 2-Fluoro-3-iodo-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 951626-91-8, 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]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, Recommanded Product: 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine, blongs to pyridine-derivatives compound. Recommanded Product: 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine

5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine (235 mg) was dissolved in dichloromethane (5 ml). Di-tert-butyl dicarbonate (248 mg) and N,N-dimethylaminopyridine (1.2 mg) were added and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (297 mg).MS (ESI) m/z: 331 (M+H)+.1H-NMR (CDCl3) delta: 1.67 (9H, s), 7.65 (1H, s), 8.05 (1H, d, J=2.2 Hz), 8.58 (1H, d, J=2.2 Hz).

The synthetic route of 951626-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; US2011/82138; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13603-44-6, 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. 13603-44-6, name is 2,6-Dimethylpyridin-4-ol. A new synthetic method of this compound is introduced below.

2,6-Dimethyl-pyridin-4-yl trifluoromethanesulfoiiate (91)A suspension of pyridone 90 (5.0 g, 40.6 mmol) in DCM (100 mL) at O0C was treated with triethylamine (8.50 mL, 60.9 mmol) followed by trifluoromethane- sulfonic anhydride (10.2 mL, 60.9 mmol), added dropwise via syringe over 5 minutes. After warming to RT and stirring 2 h, the reaction mixture was washed with aqueous NaHCO3 (3 x 100 mL) and reduced in vacuo to afford the title compound.Yield: 9.25 g (quant.).LC/MS ttau 0.96 min.MS(ES+) m/z 256 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13603-44-6, 2,6-Dimethylpyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; WYETH; WO2007/89669; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 884495-39-0, 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. 884495-39-0, name is 5-Bromo-2-methoxypyridin-3-amine, molecular formula is C6H7BrN2O, 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.

A mixture of 1.80 g (8.8 mmol) C-5, 2.29 mL (17 mmol) 2,4-difluorobenzenesulphonyl chloride, 1.07 mL (13.3 mmol) pyridine and 20 mL DCM is stirred at RT over night.100 mL DCM is added and the reaction mixture is extracted three times with 50 mL aqueous 1M HCl. The organic layer is dried over MgS04 and the solvent is removed under reduced pressure. The solid is dissolved in water/MeCN and further purified by RP- chromatograpy. Yield: 2,9 g (86%).

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 884495-39-0, 5-Bromo-2-methoxypyridin-3-amine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WUNBERG, Tobias; VEEN, VAN DER, Lars; KRAEMER, Oliver; WO2012/101184; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54221-95-3, 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. 54221-95-3, name is 2-Acetylaminoisonicotinic acid, molecular formula is C8H8N2O3, 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.

2-Amino-isonicotinic acid methyl ester (2-3) 2-Acetylamino-isonicotinic acid (3.10 g, 17.2 mmol) was stirred in 35 mL MeOH at 0° C. HCl (g) was bubbled through the solution for 10 minutes and then the reaction was heated to reflux. After 16 hours the reaction was concentrated in vacuo. The residue was diluted with water and the pH was adjusted to 7 with Na2CO3 (s). A white precipitate formed which was filtered to afford a portion of pure desired product. The aqueous phase was extracted three times with 95:5 dichloromethane (DCM)/nBuOH. The organic phases were dried over Na2SO4, filtered and concentrated to afford more of the pure product as a white solid. 1H NMR (CDCl3) delta8.19 (d, 1H, J=5.3 Hz), 7.17 (dd, 1H, J=1.4, 5.3 Hz), 7.07 (d, 1H, J=1.3 Hz), 4.64 (bs, 2H), 3.92 (s, 3H). MS [M+H]+=153.0.

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 54221-95-3, 2-Acetylaminoisonicotinic acid.

Reference:
Patent; Ren, Yu; Karki, Shyam B.; Zhao, Matthew M.; Bidodeau, Mark T.; US2004/23981; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7356-60-7 , The common heterocyclic compound, 7356-60-7, name is Nicotinimidamide hydrochloride, molecular formula is C6H8ClN3, 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.

Put compound A (10g, 23.03mmole) and 3,5-dibromobenzaldehyde (6.63g, 25.12mmole) in the reaction tank. After fully removing the water, add 150 ml of ethanol and start stirring. Then, sodium methoxide (0.33 g, 6.2 mmole) was added, and the mixture was stirred at room temperature for 16 hours. Thereafter, 3-Amidinopyridinium chloride (3.96 g, 25.13 mmole) and sodium hydroxide (1.6 g, 40.3 mmole) were added, and 30 ml of toluene was added thereto. The heating device was turned on and heated until 75 C and reacted overnight. After the reaction was completed, the solid was collected by filtration, heated and stirred with 250 ml of toluene, and the solid was filtered to obtain a milky white compound G (about 4.7 g).

The synthetic route of 7356-60-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yulei Optoelectric Technology Co., Ltd.; Huang Helong; Zhao Dengzhi; Xu Bowei; Lai Zhenchang; Yin Lijia; Zhang Minzhong; (32 pag.)CN110746412; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1211540-92-9, Adding some certain compound to certain chemical reactions, such as: 1211540-92-9, name is 3-Bromo-4-chloro-5-fluoropyridine,molecular formula is C5H2BrClFN, 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 1211540-92-9.

Preparation 9: (l-(3-amino-5-fluoropyridin-4-yl)piperidin-4-yl)(4-methylpiperazin-l- yl)methanone (hydrochloride) 17 Scheme 4 Step 1: 3-bromo-4-chloro-5-fluoropyridine hydrochloride 18 [00264] To a solution of diisopropylamine (6.899 g, 9.555 mL, 68.18 mmol) in THF (75 mL) cooled to -78C, was added butyllithium (25 mL of 2.5 M in hexanes, 62.5 mmol). The reaction mixture was allowed to warm to -20C then cooled back down to -78C. A solution of 3-bromo-5-fluoro-pyridine (10 g, 56.82 mmol) in THF (25 mL) was added dropwise keeping temperature below -70C (approx 30 mins). The reaction mixture was stirred at – 78C for 30 min and a solution of 1, 1, 1,2,2,2-hexachloroethane (14.8 g, 62.5 mmol) in THF (20 mL) was then added dropwise, keeping temperature below -70C (over approx 30 mins). The mixture was stirred at -78C for 20 minutes, allowed to warm to room temperature, cooled back to 0C and quenched with water (100 mL). EtOAc (400 mL) was then added, and organic layer separated, washed with water (2x), brine (lx), dried (MgS04), filtered and concentrated in vacuo to leave a brown solid. The solid was triturated in pentane (lOOmL) for 10 minutes, then filtered. The filtrate was concentrated in vacuo to afford product as a brown 011 that turned to a crystalline solid on standing, 11.85 g, 89%). 1H NMR (DMSO-d6) delta 8.78 (s, 1H), 8.76 (s, 1H). [00265] To a solution of 3-bromo-4-chloro-5-fluoro-pyridine (7.56 g, 32.18 mmol) in pentane (100 mL) was added hydrogen chloride (2M in ether) (17.7 mL of 2 M, 35.4 mmol). An off-white precipitate formed instantly. The mixture was stirred for 5 minutes then the solid was collected by filtration, washed with pentane and dried by suction to afford the desired product as an off-white solid (4.79 g, 60%). 1H NMR (DMSO-d6) delta 8.77 (s, 1H), 8.75 (s, 1H).

According to the analysis of related databases, 1211540-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DAVID, Chris; DURRANT, Steven; FRAYSSE, Damien; JIMENEZ, Juan-Miguel; KAY, Dave; KNEGTEL, Ronald; O’DONNELL, Michael; PIERARD, Francoise; PINDER, Joanne; STORCK, Pierre-Henri; TWIN, Heather; WO2014/143242; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 20173-24-4, 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.20173-24-4, name is 2-(Pyridin-3-yl)ethanamine, molecular formula is C7H10N2, molecular weight is 122.1677, as common compound, the synthetic route is as follows.

Reference Example 19 (4-Chloro-6-morpholin-4-yl-pyrimidin-2-yl)-(2-pyridin-3-yl-ethvD-amine; 4-(2,6-Dichloro-pyrimidin-4-yl)-moipholine was prepared as described inWO2006/060194.To a stirred solution of 4-(2,6-dichloro-pyrimidin-4-yl)-morpholine (936 mg; 4.0 mmol) and DIPEA (0.77 ml; 4.4 mmol) in dioxane (10 ml) at 5C was added 3-(2- aminoethyl)pyridine (0.53 ml; 4.4 mmol). The cooling bath was removed and the reaction mixture stirred at r.t. for 5 h then heated at 70C for 40 h. Volatiles were removed in vacuo and the residue purified by flash chromatography (95:5 EtOAc/MeOH as eluent) to afford the title compound as a white crystalline solid (963 mg; 75 %). deltaH (400 MHz, CDCl3) 2.91 (t, J = 7.2, 2H), 3.57 (t, J = 4.8, 4H), 3.66 (q, J = 7.2, 2H), 3.77 (t, J = 4.8, 4H), 5.00 (br s, IH), 5.90 (s, IH), 7.24 (dd, J = 7.6 and 4.8, IH), 7.55 (d, J = 7.6, IH), 8.49-8.51 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 20173-24-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125839; (2008); A2;,
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. 1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Synthesis of methyl 6-bromo-5-fluoropicolinate To a solution of 6-bromo-5-fluoropicolinic acid (1.0 equiv.) in methanol (0.2 M) was added H2SO4 (4.2 equiv.) and the reaction was stirred at room temperature for two hours. Upon completion of the reaction as monitored by LC/MS, the reaction was diluted with ethyl acetate and quenched slowly with saturated aqueous NaHC03. The reaction was poured into a separatory funnel and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate, filtered, and concentrated in vacuo to provide methyl 6-bromo-5-fiuoropicolinate as a white solid (>99%). LC/MS = 233.9/235.9 (M+H), Rt = 0.69 min.

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, 1052714-46-1, 6-Bromo-5-fluoropicolinic acid.

Reference:
Patent; NOVARTIS AG; BURGER, Matthew; DRUMM III, Joseph; NISHIGUCHI, Gisele; RICO, Alice; SIMMONS, Robert Lowell; TAFT, Benjamin; TANNER, Huw; WO2013/175388; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem