Day: November 13, 2020

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 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

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

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

Adding a certain compound to certain chemical reactions, such as: 626-64-2, Pyridin-4-ol, 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, 626-64-2, blongs to pyridine-derivatives compound. 626-64-2

To a mixture of 4-hydroxypyridine (0.953 g, 10 mmol) and DBU (2.3 mL, 15 mmol, 1.5 equiv) in DMF (20 mL) was added p-methoxybenzyl chloride (2.0 mL, 15 mmol, 1.5 equiv). The reaction mixture was stirred at 66 C for 4 h. After cooling to the room temperature, the solvent was removed under reduced pressure. The residue was partitioned between CHCl3 and H2O. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous MgSO4, and then concentrated under reduced pressure. The residue was purified by flash column chromatography (CHCl3/MeOH=9:1, Rf=0.30) to give the white solid (11, 1.89 g, 8.8 mmol, 88%). Mp 166-168 C (from column); 1H NMR (CDCl3, 400 MHz) delta 7.35 (d, 2H, J=7.6 Hz, CH), 7.12 (d, 2H, J=8.8 Hz, CH), 6.88 (d, 2H, J=8.8 Hz, CH), 6.31 (d, 2H, J=7.6 Hz, CH), 4.87 (s, 2H, CH2), 3.77 (s, 3H, CH3); 13C NMR (CDCl3, 100 MHz) delta 178.8, 159.9, 139.9 (CH), 129.1 (CH), 126.7, 118.5 (CH), 114.5 (CH), 59.5 (CH2), 55.3 (CH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,626-64-2, its application will become more common.

Reference:
Article; Cheng, Chien; Shih, Yu-Chiao; Chen, Hui-Ting; Chien, Tun-Cheng; Tetrahedron; vol. 69; 4; (2013); p. 1387 – 1396;,
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

571188-59-5 , The common heterocyclic compound, 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, molecular formula is C14H22N4O2, 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.

Toluene (432.0 mL) and 4-(6-amino-pyridine-3-yl)-piperazine-l -carboxylic acid tert-butyl ester (34.3g, 0.123 moles) were charged into 2L 4N RB flask under nitrogen atmosphere at 30¡À5C and stirred for 5-10 min to get brown colored suspension. Reaction mass was cooled to 0¡À5C. Lithium hexamethyldisilazane 1M solution in THF (259.0 mL, 0.258 moles) was added dropwise to the reaction mass through addition funnel by maintaining the reaction mass temperature at 0 ¡À5C. And stirred the reaction mass for 10-15 min at 0 ¡À 5Cto get clear brown colored solution. Add the solution of 2-chloro-7-cyclopentyl-N,N-dimethyl-pyrrolo[2,3-d]pyrimidine- 6-carboxamide (36.0g, 0.123 moles) in 324.0 mL of toluene dropwise to the reaction mass through addition funnel at 0 ¡À5C. Reaction mass temperature was raised to 25- 35C and stirred for lh for reaction completion. (0107) After completion of reaction (by TLC), solvent was distilled off on rotavapor under vacuum at 55-60C to get the brown colored solid. DM water (360.0 mL) and aq. sodium bicarbonate solution (36.0g of sodium bicarbonate was dissolved in 720.0 mL of DM water) were added to the above solid and stirred for 10-15 min. Then methylene chloride (720 mL) was charged to the above solution and stirred for 5-l0min. Layers were separated. Organic layer washed with DM water (720 mL) and layers Separated. Solvent was distilled off from organic layer completely under vacuum at 45-50C on rotavapor to obtain brown colored solid. The solid was leached with methanol (180 mL) at 30 ¡À 5C to afford title compound as pale brown colour solid. Weight of the product: 57.0g (86.6% by theory). Purity by HPLC > 98.0%. (0108) H1 NMR (DMSO-d6): d 9.412 (S, 1 H), 8.167-8.190 (d, 2 H), 8.02-8.03 (d, 1 H), 7.449-7.479 (dd, 1 H), 6.603 (S, 1 H), 4.690-4.778 (m, 1 H), 3.472-3.484 (d, 4 H), 3.062-3.073 (d, 10H), 2.413-2.465 (m, 12 H), 1.92-1.991 (m, 4 H), 1.427-1.65 (m, 10H); Mass m/z (M+l): 535.25

According to the analysis of related databases, 571188-59-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; ARUNKUMAR, Thiriveedhi; SWAPNA, Kondaveeti; SATHISH, Thumati; NARESH, Ghanta; JANAKI RAMA RAO, Ravi; DURGA PRASAD, Konakanchi; PULLA REDDY, Muddasani; VENKAIAH CHOWDARY, Nannapaneni; (36 pag.)WO2019/142206; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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

Adding some certain compound to certain chemical reactions, such as: 109-04-6, name is 2-Bromopyridine, 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 109-04-6. 109-04-6

To a 250 mL flask were charged 2-bromopyridine (4.8 mL, 49 mmol), 2-bromophenylboronic acid (9.85 g, 49 mmol), triphenylphosphine (1.09 g, 4.17 mmol), and ethylene glycol dimethyl ether (55 mL). A homogeneous solution was formed. To this solution was added 2 M K2CO3 (60 mL, 120 mmol). The mixture was purged with nitrogen then Pd(OAc)2 (0.24 g, 1 mmol) was added. The mixture was refluxed for 5 h then cooled to room temperature. The reaction mixture was transferred into a separating funnel and the organic layer was separated and retained. The aqueous phase was extracted with ethyl acetate (EtOAc) (4¡Á100 mL). The combined organic layers were washed with water (200 mL) and brine (200 mL) and dried over MgSO4. Filtration and evaporation produced a dark brown oil, which was purified by chromatography on silica gel with CH2Cl2_heptane=2:1 and CH2Cl2 to provide a light yellow oil, 7.57 g, 65%.

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 109-04-6.

Reference:
Patent; Eastman Kodak Company; US6835835; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

13472-85-0, 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 13472-85-0, name is 5-Bromo-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2. 5-Hydroxy-2-methoxypyridine To a stirred solution of 5-bromo-2-methoxypyridine (8.9 g, 47.9 mmol) in THF (175 mL) at -78 C. was added an n-butyllithium solution (2.5 M in hexane; 28.7 mL, 71.8 mmol) dropwise and the resulting mixture was allowed to stir at -78 C. for 45 min. Trimethyl borate (7.06 mL, 62.2 mmol) was added via syringe and the resulting mixture was stirred for an additional 2 h. The bright orange reaction mixture was warmed to 0 C. and was treated with a mixture of a 3 N NaOH solution (25 mL, 71.77 mmol) and a hydrogen peroxide solution (30%; approx. 50 mL). The resulting yellow and slightly turbid reaction mixture was warmed to room temp. for 30 min and then heated to the reflux temp. for 1 h. The reaction mixture was then allowed to cool to room temp. The squares layer was neutralized with a 1N HCl solution then extracted with Et2O (2*100 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to give a viscous yellow oil (3.5 g, 60%).

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 13472-85-0, 5-Bromo-2-methoxypyridine.

Reference:
Patent; BAYER CORPORATION; US2003/207914; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem