Category: pyridine-derivatives

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.609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, molecular formula is C6H5NO3, molecular weight is 139.1088, as common compound, the synthetic route is as follows.609-71-2

This compound was prepared according to the procedure of Y. S. Lo (Synthetic Communications, 1989, 553). Bromine (0.77 eq) was added dropwise at 0C to a stirred solution of 50% NAOH (2.4 eq) in water (1 M solution). After 5 min, 50% NAOH (3 eq) followed by solid 2- hydroxynicotinic acid (1 eq) was added to the mixture and the resulting solution was stirred at 50C. After 20 h, a solution prepared by adding bromine (0. 38 eq) to 50% NAOH (1. 2 eq) in water (1 M solution) was added to the reaction mixture and stirring continued for another 24 h at 50C. After that time the reaction mixture was cooled to 0C and acidified to pH 2 with concentrated hydrochloric acid to allow the formation of a solid which was isolated by filtration, washed with warm water/isopropanol (3: 1), then with diethyl ether and dried to afford 5-bromo-2- hydroxynicotinic acid (87%) as an off-white solid. OH (400 MHz; DMSO) 8.25 (1H, d, J 2.7), 8.33 (1H, d, J 2.7), 13.84 (2H, bs) ; BC (400 MHZ ; DMSO) 99.45, 117.97, 142.01, 147.42, 163.22, 163.88 ; M/Z (ES-) 218-216 (M-H)-.

Statistics shows that 609-71-2 is playing an increasingly important role. we look forward to future research findings about 2-Oxo-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2004/110442; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-18-8, Adding a certain compound to certain chemical reactions, such as: 5470-18-8, 2-Chloro-3-nitropyridine, 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, 5470-18-8, blongs to pyridine-derivatives compound.

General procedure: To a solution of amine (1.2 mmol) dissolved in 20% DES,aryl halide (1 mmol) was added at room temperature andstirred for appropriate time. The progress of the reactionwas monitored by TLC. After completion of the reactioncold water was added to the reaction mixture. The precipitatedsolid was filtered off, and recrystallized using ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5470-18-8, its application will become more common.

Reference:
Article; Pant, Preeti Lalit; Shankarling, Ganapati Subray; Catalysis Letters; vol. 147; 6; (2017); p. 1371 – 1378;,
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. 626-64-2, name is Pyridin-4-ol, the common compound, a new synthetic route is introduced below. 626-64-2

A solution of an alcohol (0.4 mmol), a phenol/thiophenol (0.4 mmol), diisopro-pylethylamin (0.44 mmol) and tributylphosphine (0.52 mmol) in THF (5 mL) was stirred undernitrogen at rt. 1,1′-(Azodicarbonyl)dipiperidine (ADDP, 0.52 mmol) dissolved in THF (5 mL)was added and the reaction mixture was stirred at rt for 16 h. The reaction mixture was fil- tered and the filtrate was evaporated to dryness, which gave a crude which was either puri- fied by flash chromatography (Quad flash 25, EtOAc-heptane) or redissolved in MeCN andpurified by preparative HPLC (Gilson).Example 1 (General procedure 1)Methyl-phenyl-carbamic acid 4-[2-(pyridin-4-yloxy)-ethyl]-phenyl esterThe title compound (99%) was prepared as an oil using methyl-phenyl-carbamic acid 4-(2-hydroxy-ethyl)-phenyl ester and 4-hydroxypyridine.HPLC-MS : mlz = 349.2 (M+1); R, = 2.64 min.

Statistics shows that 626-64-2 is playing an increasingly important role. we look forward to future research findings about Pyridin-4-ol.

Reference:
Patent; NOVO NORDISK A/S; WO2004/111006; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16063-70-0, 2,3,5-Trichloropyridine, 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, 16063-70-0, blongs to pyridine-derivatives compound. 16063-70-0

To a solution of ethyl (2E) -3- [2-hydroxy-4- (2- methoxyethoxy) phenyl] acrylate (900 mg) in N,N- dimethylformamide .(15 ml) was added sodium hydride (60% in oil, 188 mg) , and the mixture was stirred at room temperature for 1 hr. 2, 3, 5-Trichloropyridine (925 mg) was added to the reaction mixture, and the. mixture was stirred at 800C for 36 hr. After cooling, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) , and concentrated. The obtained residue was subjected to silica EPO gel column chromatography, and eluted with ethyl acetate- hexane (1:4, v/v) . The obtained crude crystals were recrystallized from ethyl acetate-hexane to give ethyl (2E) -3- [2- [ (3, 5-dichloropyridin-2-yl) oxy] -4- (2- methoxyethoxy) phenyl] acrylate (1.01 g, yield: 72%) as colorless crystals, melting point 70.7-71.30C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16063-70-0, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/18314; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0 , The common heterocyclic compound, 766-11-0, name is 5-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, 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.

Example 51; 4-[{2-[(6-Fluoro-3-pyridinyl)oxy]ethyl}(2,2,2-trifluoroethyl)amino]-2- (trifluoromethyl)benzonitrile; A. 6-Fluoro-3-pyridinol; To a solution of 5-bromo-2-fluoropyridine (0.26 mL, 2.5 mmol) in dry Et2O (10 mL) at -78C was added n-BuLi (1.06 mL of a 2.5 M solution in hexanes, 2.7 mmol), dropwise over 3 min. The mixture was stirred 15 min and B(O/-Pr)3 (0.64 mL, 2.8 mmol) was added dropwise. The mixture was gradually warmed to rt over 30 min, 1 M NaOH (2 mL) was added, followed by H2O2 (0.5 mL of a 30 wt% solution) and the mixture was stirred 30 min. Excess H2O2 was quenched by dropwise addition of a 10% solution of Na2S2O3, the mixture was poured into water and the layers were separated. The aqueous layer was adjusted to pH 3.5 by addition of 1M KHSO4 and extracted with EtOAc (x3). Combined organics portions were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.242 g of the title compound as a colorless solid: MS (APCI) m/z 114 (M+H).

The synthetic route of 766-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/44707; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-70-2, 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.5470-70-2, name is Methyl 6-methylnicotinate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.

A mixture of methyl 6-methylnicotinate (5.0 g, 33.0 mmol), 12 (8.4 g, 33.2 mmol) andTFA (7.5 mL, 11.5 g, 0.1 mol) in DMSO (100 mL) was heated to 160¡ãC for 2 h. Themixture was allowed to cool to RT and poured into a 1 N solution ofNa2S2O3 (aq.) (0.5L) solution, made alkaline using NaOH (2 N) and extracted with EtOAc (3 x 0.2 L).The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in DCM and applied on a short pad of silica. The product was eluted with EtOAc to afford the product as a yellowish solid (3.8 g, 23 mmol, 70percent).

Statistics shows that 5470-70-2 is playing an increasingly important role. we look forward to future research findings about Methyl 6-methylnicotinate.

Reference:
Patent; AAPA B.V.; HEERES, Andre; WILLIGERS – HOGG, Sandra; BORST, Marcus Leonardus Gerardus; DROeGE, Melloney Joyce; WO2015/69110; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-70-2, 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. 5470-70-2, name is Methyl 6-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 6-methylnicotinate (30 g, 197 mmol) and NBS (52.7 g, 296 mmol) in CC14 (300 mL) was added AIBN (3 g). Then the reaction mixture was heated to 80 C and stirred overnight. Then the reaction mixture was cooled and filtered, and the filtrate was concentrated under vacuum to give a crude residue. The crude residue was purified by silica gel column chromatography (PE/EA = 5/1) to give methyl 6-(bromomethyl)nicotinate (10 g, yield 22.2 %). 1H NMR (400MHz, CDC13) 5 = 9.17 (d, J=1.5 Hz, 1H), 8.30 (dd, J=2.0, 8.0 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 4.58 (s, 2H), 3.96 (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 5470-70-2, Methyl 6-methylnicotinate.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); 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. 65753-47-1, name is 2-Chloro-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. 65753-47-1

EXAMPLE 2Synthesis of Additional Representative Substituted Biaryl Ouinolin-4-ylamine AnaloguesA. 5-Trifluoromethyl-6-[8-(‘5-trifluoromethyl-pyridm-2-ylammo)-pyrido[2,3-&lpyrazin-3-yll- nicotinamide (compound 4) 1. 2-Methoxy-3-trifluoromethyl-pyridine Heat a mixture of 2-chloro-3-trifluoromethyl-pyridine (1.8 g, 10 mmol) and sodium methoxide (4M, 5 mL, 20 mmol) in MeOH (20 mL) at reflux for 18 hours. Cool the mixture and remove the volatiles by rotary evaporation. Dissolve the residue in EtOAc (50 mL) and wash with water (50 mL), saturated NaHCO3(aq) (50 mL) and brine (50 mL). Dry the organic extract overMgSO4 and remove the solvent under reduced pressure to yield the title compound.

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, 65753-47-1, 2-Chloro-3-(trifluoromethyl)pyridine.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/42289; (2006); A2;,
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. 117977-21-6, name is 2-[[[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl ]methyl]thio]-1H-benzimidazole. A new synthetic method of this compound is introduced below., 117977-21-6

Example 3 Preparation of 2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridinyl]methyi]- sulfinyl]-lH-benzimidazole sodium (Rabeprazole Sodium) 2-[[ [4 -(3 -methoxy-propoxy)-3 -methyl-2-pyridinyl]methyl] -thio]-1 H benzimidazole (25 g) was suspended in 500 ml of Purified Water, Sodium hydroxide (5 g) and Pyridine (12.5 ml). To this was slowly added about 160 g of Sodium hypochlorite solution having a chlorine content of 3.2 % at 5-10 C in 2 hours. The reaction mass was maintained at 5 – 8 C for 2 hours. After completion of the reaction, excess Sodium hypochlorite was decomposed using 5% aqueous Sodium thiosulphate solution. The reaction mass was then saturated with 150 g of Sodium chloride and extracted with 250 ml of dichloromethane twice. The organic layer was then dried over anhydrous Sodium sulphate. Concentrating the organic layer under vacuum yielded a residue to which 125 ml of Ethyl acetate was added and heated to 45 – 50 C for dissolution. This solution was slowly added to 500 ml of n-Heptane under stirring and stirred for 2 hours. EPO The solids were filtered under nitrogen atmosphere, washed with n-Heptane and dried in an oven at 45-50 C to give 20 g of Rabeprazole sodium.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117977-21-6, 2-[[[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl ]methyl]thio]-1H-benzimidazole, and friends who are interested can also refer to it.

Reference:
Patent; CIPLA LIMITED; PATHI, Srinivas, Laxminarayan; KANKAN, Rajendra, Narayanrao; RAO, Dharmaraj, Ramachandra; WO2006/117802; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

6419-36-9, 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. 6419-36-9, name is 2-(Pyridin-3-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

Example 3; Preparation of 3-pyridyl-1-hydroxyethylidene-1, 1-bisphosphonic acid monosodium salt in the presence of olive oil; The procedure of Example I is repeated except olive oil is used as the emulsifying agent instead of sunflower oil. The analysis confirmed the identity of the product and the absence of impurities. Overall yield of 27.0 % is obtained.

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. 6419-36-9, 2-(Pyridin-3-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EOS Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ti Caret A.S.; EP1798236; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem