Tag: M.W:100-200

100-48-1 , The common heterocyclic compound, 100-48-1, name is Isonicotinonitrile, molecular formula is C6H4N2, 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.

NaOMe (5.4 g, 100 mmol) was added to a stirred solution of 4-pyridinecarbonitrile (10.0 g, 96.1 mmol) in dry MeOH (50 mL) and the mixture stirred at reflux temperature for 2 h. NH4Cl (11.0 g, 211 mmol) was added and the mixture stirred at reflux temperature for 2 h. The solvent was evaporated and the residue crystallised from water to give amidine*HCl 58 (7.54 g, 65percent) as a white powder: mp (H2O) 235-238 ¡ãC (lit.2 mp [H2O] 236-242 ¡ãC); 1H NMR d 9.51 (br s, 4 H, NH, NH2*HCl), 8.87 (dd, J = 4.4, 1.7 Hz, 2 H, H-2, H-6), 7.78 (dd, J = 4.4, 1.7 Hz, 2 H, H-3, H-5).

The synthetic route of 100-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bonnet, Muriel; Flanagan, Jack U.; Chan, Denise A.; Lai, Edwin W.; Nguyen, Phuong; Giaccia, Amato J.; Hay, Michael P.; Bioorganic and Medicinal Chemistry; vol. 19; 11; (2011); p. 3347 – 3356;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

4926-28-7 , The common heterocyclic compound, 4926-28-7, name is 2-Bromo-4-methylpyridine, molecular formula is C6H6BrN, 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-bromo-4-methylpyridine (1 g, 5.81mmol), NBS (1.1 g, 6.39 mmol) and a catalytic amount of AIBN (100 mg) in CCL (10 mL) was stirred at 80 C overnight. The resulting mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: PE/EtOAc = 200/1) to give the desired product (500 mg).

According to the analysis of related databases, 4926-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; CIANCHETTA, Giovanni; LIU, Tao; PADYANA, Anil, Kumar; SUI, Zhihua; CAI, Zhenwei; CUI, Dawei; JI, Jingjing; (294 pag.)WO2019/35863; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

636-73-7, Adding a certain compound to certain chemical reactions, such as: 636-73-7, Pyridine-3-sulfonic 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, 636-73-7, blongs to pyridine-derivatives compound.

Pyridine-3-sulfonic acid (125 g, 0.78 m) was placed in a 1L, 3-necked flask equipped with mechanical stirrer, reflux condenser, thermometer and nitrogen inlet. Next, the phosphorus pentachloride (250 g, 1.19 m, 1.5 eq) was added, followed immediately by the phosphorus oxychloride (330 ml, 3.8 m, 4.5 eq). The contents of flask were initially stirred at ambient temperature for 30 min, then brought slowly to gentle reflux (internal temp. approx. 110¡ã C.) over the next hour, kept at this temperature for approx. 3.5 hr then allowed over the next 12 hr to cool back to ambient temperature. Gas evolution was observed during this time. The volatiles were stripped under reduced pressure (at 12 mmHg/40¡ã C.) and yellow semi-solid residue was diluted with DCM (1 L). The slurry was poured slowly into the stirred, ice-cold sat. aq. bicarbonate, maintaining pH=7. Gas evolution was observed. The organic layer was separated and aqueous layer was back-extracted with DCM. The combined extracts were washed with cold sat. aq. bicarbonate, brine and dried with magnesium sulfate. The solids were filtered off and filtrate evaporated, leaving pyridine-3-sulfonyl chloride as a pale yellow, oily liquid, 123 g (93percent pure; 88percent theory).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,636-73-7, its application will become more common.

Reference:
Patent; Elan Pharmaceutical Inc.; US2006/13799; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A common compound: 108-75-8, name is 2,4,6-Trimethylpyridine,molecular formula is C8H11N, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 108-75-8

Step A. A solution of 2,4,6-collidine (1 mmole) in carbon tetrachloride was treated with NBS (5 mmole) and dibenzoyl peroxide (0.25 mmole) at 80 C. for 12 h.. The reaction mixture was cooled to 0 C. and the precipitate was filtered.. The filtrate was concentrated under vacuum.. Chromatography gave 2-bromomethyl-4,6-dimethylpyridine.

With the rapid development of chemical substances, we look forward to future research findings about 108-75-8.

Reference:
Patent; Metabasis Therapeutics, Inc.; US6756360; (2004); B1;,
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 823-56-3, name is 2-Fluoro-3,5-dichloropyridine. This compound has unique chemical properties. The synthetic route is as follows. 823-56-3

5.0Og (0.030 mol) of 3,5-dichloro-2-fluoropyridine and 5.01g of 1-(1- cyclohexen-l-yl)pyrrolidine (0.033 mol) are stirred neat together at room temperature for Ih and are left at room temperature overnight. The reaction mixture is quenched with 40ml of sulfuric acid 2M. Water is added to the reaction mixture (100 ml) which is extracted thrice with ethyl acetate (50 ml). The combined organic phases are washed with water (150 ml) and brine (100 ml). After separation, the organic phase is dried over magnesium sulfate filtered, concentrated to dryness and purified on silica gel to yield to 0.22 g of 2-[3,5-dichloro-2-pyridinyl]cyclohexanone

Statistics shows that 823-56-3 is playing an increasingly important role. we look forward to future research findings about 2-Fluoro-3,5-dichloropyridine.

Reference:
Patent; BAYER CROPSCIENCE SA; WO2006/122952; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 108-48-5, name is 2,6-Dimethylpyridine, molecular formula is C7H9N, 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. 108-48-5

2,6-Lutidine (i) (5.1 g, 47.5 mmol, 1 equiv.) was dissolved in 300 mL of carbon tetrachloride, and the solution was degassed with argon. Azobisisobutyronitrile (AIBN, 0.8 g, 4.8 mmol, 0.1 equiv.) and N-bromosuccinimide (NBS, 9.3 g, 52.3 mmol, 1.1 equiv.) were added to the solution of i in small portions over a period of 3 h, while the reaction mixture was heated at 60 C (Scheme S1). The reaction mixture was irradiated with UV light throughout the reaction. After the addition was complete, the reaction mixture was refluxed for another 8 h. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated in vacuo producing a brown residue, which was subject to SiO2 column chromatography using a gradient of ethyl acetate from 10 to 20% in hexanes. Pure fractions were combined, and solvent was removed in vacuo to afford a yellow oil. The product solidified in the freezer producing slightly pinkish white needles. Yield: 4.0 g, 46%. 1H NMR, 400 MHz (CDCl3, ppm): delta = 7.55 t (1H, Ar), 7.22 d (1H, Ar), 7.04 d (1 H, Ar), 4.49 s (2H, CH2), 2.53 s (3 H, CH3). 13C NMR, 75 MHz (CDCl3, ppm): delta = 158.38, 156.04, 137.16, 122.59, 120.39, 34.08, 24.36. ESI-MS (m/z): [M + H]+, calculated: 186.0, found: 186.0.

The chemical industry reduces the impact on the environment during synthesis 108-48-5, I believe this compound will play a more active role in future production and life.

Reference:
Conference Paper; Dorazio, Sarina J.; Tsitovich, Pavel B.; Gardina, Stephanie A.; Morrow, Janet R.; Journal of Inorganic Biochemistry; vol. 117; (2012); p. 212 – 219;,
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 74115-13-2, name is 5-Bromo-3-pyridinol. This compound has unique chemical properties. The synthetic route is as follows. 74115-13-2

Di-tert-butyl dicarbonate (4.3 g, 19.7 mmol) was added to a cold (O0C) mixture of 2-(S)- pyrrolidinemethanol 4 (2 g, 19.7 mmol) and triethylamine (2.8 mL, 20 mmol). After the mixture was stirred at room temperature for 30 min, 20 mL of dichloromethane were added and washed with saturated NaHCCbeta (2 x 20 mL) and water (1 x 20 mL). The organic layer was dried (MgSO4), filtered, and concentrated to provide l-BOC-2-(S)-pyrrolidinemethanol 5 (3.5 g, 88%) in >95% purity (MS, m/z, 224 (65%, [M+Na]+). Diethyl azodicarboxylate (DEAD) (1.8 mL, 12 mmol) was added to a solution of triphenylphosphine (3.1 g, 12 mmol) in anhydrous tetrahydrofuran (THF) (30 mL) at O0C, and the mixture was stirred for 30 min. A solution of l-BOC-2-(S)-pyrrolidinemethanol (5) (2 g, 10 mmol) in 5 mL THF and 3- bromo-5-hydroxypyridine (3) (2 g, 11.4 mmol) in 5 mL THF was added at O0C. The reaction mixture was allowed to stand at room temperature for 24 h. The solvent was removed by rotary evaporation and the residue was dissolved in dichloromethane (100 mL) and washed with saturated NaHCO3 (50 mL) and water (3 x 50 mL). The organic solution was dried over anhydrous MgSO4, filtered, and concentrated to oil. The crude oil was purified by silica column chromatography (hexane/ethyl acetate, 1 :1) to afford the title compound 6 (1.56 g, 44%). NMR: (CDC13, 500 MHz) -ppm: 8.26 (dd, 2H, J = 15, 1.8 Hz), 7.37 (t,lH, J = 2.4 Hz), 3.92 (dm, 2H, J = 34.7 Hz), 3.54 (m, IH), 3.01 (m, 2H), 1.93 (m, 2H), 1.79 (m, 2H), 1.65 (s, 9H). MS, m/z, 379, 381 (5%, [M+Na]+).

Statistics shows that 74115-13-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-pyridinol.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2006/86068; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-70-2, 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 5470-70-2 as follows.

A solution of methyl 6-.methylnicolinate (15 g, 9934 n:imoi) and m-CPBA (18,8 g, 109.3mmol) in DCM (100 rnL) was stirred at room temperature for 4 hours. The reaction mixture wasquenched with 200 mL of saturated aqueous Na2SO3 and 100 mL of saturated aqueous NaHCO3. The resulting mixture was extracted with EA (20() mLx3), The combined EA layer was washed with brine and dried over Na2SO4. Filtered and the filtrate was concentrated. The residue was purified by colunm chromatography on silica gel (PE/EtOAc = 5/i) to afford 5-(methoxycarbonyi)-2-methylpyridine 1-oxide as a solid. MS-ESI (m/z): 168.2 (M+1) (LC-MSmethod 1); Ret. time: 0.32 mm).

The chemical industry reduces the impact on the environment during synthesis 5470-70-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (261 pag.)WO2016/106628; (2016); 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 98-98-6, name is Picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. 98-98-6

[00091] 4-Chloropicolinic acid methyl ester (CYD-1-1). A mixture of picolinic acid (10.0 g, 81.0 mmol, 1 equiv.) and sodium bromide (16.7 g, 162.0 mmol, 2 equiv.) in thionyl chloride (41 mL) was refluxed for 5 h at 80C. After that, the solvent was removed under the vacuum at 85C to afford the brown residue. 80 mL of anhydrous methanol was slowly added into the residue and the mixture was stirred at room temperature for half an hour. The solvent was evaporated, and the residue was taken up in the saturated sodium bicarbonate and extracted with ethyl acetate (three times). The organic layers were combined, washed with saturated brine, dried over anhydrous Na2S04 and evaporated. The residue was purified by silica gel column; eluting with 33% EtOAc in hexane afforded 4-chloropicolinic acid methyl ester (CYD-1-1) (8.0 g, 64%) as a brown solid; silica gel TLC Rf = 0.15 (1 :3 EtOAc/hexane); mp 55-56C; 1H NMR (600 MHz, CDC13) delta 8.67 (d, 1H, J = 4.8 Hz), 8.16 (d, 1H, J = 1.8 Hz), 7.51 (m, 1H), 4.04 (s, 3H).

Statistics shows that 98-98-6 is playing an increasingly important role. we look forward to future research findings about Picolinic acid.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHOU, Jia; DING, Chunyong; CUNNINGHAM, Kathryn, A.; WO2013/86266; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5223-06-3, Adding some certain compound to certain chemical reactions, such as: 5223-06-3, name is 2-(5-Ethylpyridin-2-yl)ethanol,molecular formula is C9H13NO, 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 5223-06-3.

General procedure: To a solution of A1B1 (1.0mmol) and triphenylphosphine (1.5mmol) in anhydrous tetrahydrofuran (3mL), added C1 or C2 (2.0mmol) and dropwise added diethyl azodicarboxylate (DEAD, 1.5mmol) in anhydrous and anoxybiotic conditions. The reaction mixture was stirred at-2C for 30min, and then stirred at room temperature for 24h. After completion of reaction was monitored through TLC, the reaction mixture was filtered and washed with ether and saturated salt water to get products because there would be a solid precipitate.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5223-06-3.

Reference:
Article; Wang, Fang; Sun, Jun-Rong; Huang, Mei-Yan; Wang, Hui-Ying; Sun, Ping-Hua; Lin, Jing; Chen, Wei-Min; European Journal of Medicinal Chemistry; vol. 72; (2014); p. 35 – 45;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem