Month: September 2021

Electric Literature of 73027-79-9, 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.73027-79-9, name is 4,6-Dichloronicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

To a 5000-mL 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed 4,6-dichloropyridine-3-carboxylic acid (95 g, 494.79 mmol, 1.00 equiv) and tetrahydrofuran (1000 mL), followed by the addition of BH3.THF (1 M) (2111 mL, 4.20 equiv) dropwise with stirring at 0 C. The reaction mixture was stirred at 0 C for 30 min and at room temperature overnight, quenched by the addition of 1000 mL of water/ice, and extracted with 3×1000 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 78.4 g (89%) of (4,6-dichloropyridin-3-yl)methanol as a white solid.

The chemical industry reduces the impact on the environment during synthesis 73027-79-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; VERMA, Vishal; SHORE, Daniel; VOLGRAF, Matthew; ESTRADA, Anthony A.; LYSSIKATOS, Joseph; (153 pag.)WO2018/15410; (2018); 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. 3430-27-1, name is 3-Amino-4-methylpyridine. A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2

F) Preparation of 3-Amino-2-Chloro-4-Methylpyridine STR16 3-Amino-4-methylpyridine (21.6 g, 0.2 mole) was suspended in 75 ml of water at room temperature. The mixture was dissolved by the addition of 25 ml conc. hydrochloric acid. The solution was cooled to 20 C. and 15.6 g (0.22 mole) of chlorine gas was introduced through an inlet tube reaching below the surface of the reaction mixture over 25 minutes. The mixture was stirred under a nitrogen purge for an additional 30 minutes, then cooled to 10 C. and basified by the addition of 70 mL of a 12.5 N. sodium hydroxide solution. Additional water (100 mL) was added to maintain efficient agitation of the mixture. The precipitate was collected, washed with water and dried to give 14.5 g of the title product. The aqueous phase was extracted with 3 times 100 mL of methylene chloride. The organic phases were washed with water, dried over magnesium sulfate, and concentrated to give an additional 9.4 g, mp 62-64 C. Total yield, 23.9 g (84%).

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, 3430-27-1, 3-Amino-4-methylpyridine.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US5668287; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62226-17-9 , The common heterocyclic compound, 62226-17-9, name is 4-Chlorothieno[2,3-b]pyridine, molecular formula is C7H4ClNS, 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.

To a solution of 4-chlorothieno[2,3- Z>]pyridine (450 mg, 2.65 mmol, 1 eq.) in DCM (14.7 mL) was added 3-chloroperoxybenzoic acid (1.78 g, 7.95 mmol, 3 eq.) over 15 minutes. After three hours, the reaction was quenched with 10% NaS2C>3 solution and washed with 10% K2CO3. The aqueous layer was back extracted with 3: 1 CHCI3/IPA solution. The organic layers were combined, dried (MgS04), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 500 mg (99%) of the title compound. XH NMR (400 MHz, DMSO-c) delta 8.42 (d, J = 6.6 Hz, 1H), 8.06 (d, J = 5.7 Hz, 1H), 7.65 (d, J = 6.6 Hz, 1H), 7.54 (d, J= 5.7 Hz, 1H); ES- MS [M+l]+: 186.4.

The synthetic route of 62226-17-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P., Jeffrey; BOLLINGER, Katrina A.; ENGERS, Darren W.; BLOBAUM, Anna L.; ENGERS, Julie L.; ROOK, Jerri M.; (96 pag.)WO2018/63552; (2018); 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. 126717-59-7, name is 3-Bromo-6-methoxy-2-picoline. A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrNO

The compound 3-bromo-6-methoxy-2-methylpyridine (15 g, 0.076 mol), N-bromosuccinimide (40 g, 0.22 mol),Tetrahydrofuran (100 mL), acetic acid (7.5 mL),Azobisisobutyronitrile (0.45 g, 2.7 mmol) was added to a 500 ml single-mouth flask equipped with a reflux apparatus, and the reaction system was heated to reflux for 12 hours.Cool to room temperature and add ethyl acetate (150 mL).Adjust the pH to about 8 with a saturated aqueous solution of sodium bicarbonate (40 mL).The organic phase was washed with saturated brine (30 mL) and dried over anhydrous sodium sulfate.Dry to give a clear oily mixture of compound 3-bromo-2-(dibromomethyl)-6-methoxypyridine and 3-bromo-2-(bromomethyl)-6-methoxypyridine (26 g ),Used directly in the next step.3-Bromo-2-(dibromomethyl)-6-methoxypyridine in sequence at room temperaturea mixture with 3-bromo-2-(bromomethyl)-6-methoxypyridine (26 g),Anhydrous tetrahydrofuran (100 mL), N,N-diisopropylethylamine(25.8 mL, 0.19 moL), added to a 500 ml three-neck bottle,Nitrogen protection, cooling to 0 C, diethyl phosphite(18.6 mL, 0.14 mol) was added dropwise to the reaction system.After completion, the reaction solution was stirred at normal temperature for 12 hours.Ethyl acetate (200 mL) was added to the reaction system.Wash twice with saturated brine (20 mL) and dry over anhydrous sodium sulfate.Spin dry, pass through the column (petroleum ether (v) / ethyl acetate (v) = 50:1)3-bromo-2-(bromomethyl)-6-methoxypyridine (15.5 g, two-step yield: 77%)Transparent oil.

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, 126717-59-7, 3-Bromo-6-methoxy-2-picoline.

Reference:
Patent; Wanbangde Pharmaceutical Group Co., Ltd.; Zhang Kai; (10 pag.)CN104151240; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13466-43-8, 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. 13466-43-8, name is 3-Bromopyridin-2(1H)-one, molecular formula is C5H4BrNO, 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-(Benzyloxy)-3-bromopyridine 3-bromo-2-hydroxypyridine (1.74 g, 10 mmol) was added to a suspension of NaH (440 mg of 60% dispersion in mineral oil, 11 mmol) in DMF (10 mL), and the resultant mixture was stirred at rt for 30 min. Benzyl bromide (1.3 mL, 11 mmol) was then added, and the reaction was stirred at rt overnight. It was then quenched by the addition of water, and the product extracted with ethyl acetate (2*50 mL). The extracts were combined, washed with 1N HCl solution, then dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography using hexanes to 100% ethyl acetate in hexanes as eluent to give the title compound as a colorless thick oil, (1.37 g, 52% yield). MS m/z 264, 266(MH+); 1H NMR (500 MHz, CDCl3) delta ppm 5.17 (s, 2 H) 6.05 (t, J=7.02 Hz, 1 H) 7.27-7.88 (m, 6 H) 7.70 (dd, J=7.17, 1.98 Hz, 1 H)

According to the analysis of related databases, 13466-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hudyma, Thomas W.; Zheng, Xiaofan; He, Feng; Ding, Min; Bergstrom, Carl P.; Hewawasam, Piyasena; Martin, Scott W.; Gentles, Robert G.; US2006/46983; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19798-77-7, 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.19798-77-7, name is 4-Amino-3-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

General procedure: To a solution of substituted acetylsalicyloyl chlorides (0.022 mol) in anhydrous chloroform (100 mL) was added triethylamine (0.023 mol) at 4 C. After the mixture was stirred for 5-15 min and then substituted 4-amino pyridinewas added portion wise in the ice bath. After warmed to room temperature, the solution was stirred for 24-48 h and then quenched by 1 mL of 1 M hydrochloric acid. The reaction mixture was extracted with 10 % hydrochloric acid (50, 30and 30 mL) and the combined aqueous was basified to pH 7-9 with cooled saturated sodium bicarbonate solution. The yellow precipitation was filtered producing the crude products. After recrystallized in ethanol, the products were isolated as pure form in more than 85 % yields.

Statistics shows that 19798-77-7 is playing an increasingly important role. we look forward to future research findings about 4-Amino-3-chloropyridine.

Reference:
Article; Dian, He; Zhou, De-Bin; Mou, Jian-Ping; Yang, Zhu-Qing; Zhong, Jia; Ding, Xiao-Quan; Li, Chong; Wang, Xiao-Hong; Zhang, Jian-Gang; Asian Journal of Chemistry; vol. 26; 21; (2014); p. 7269 – 7275;,
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. 56026-36-9, name is Methyl 6-(hydroxymethyl)nicotinate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Methyl 6-(hydroxymethyl)nicotinate

Step 1.; Preparation of methyl 6-((methylsulfonyloxy)methyl)nicotinate; [0121] A Catalytic amount of DMPA (dimethylol propionic acid), triethylamine (2.Og, 19.7mmol) in 20 mL CH2C12, and methanesulfonyl chloride (1.95g, 17.0mmol) are added dropwise to a solution of 6-hydroxymethyl-nicotinic methyl ester 6 (2.2g, 13.1mmol), at -78C under argon. The mixture is stirred for 5 hours at -78C and then quenched with 30 mL saturated aqueous sodium bicarbonate. The organic layer is collected and the water phase extracted with CH2C12 (2x30mL). The organic phases are combined and washed with water. The CH2C12 solution is dried over MgSO4 and concentrated to give compound 7, which is used without further purification.

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, 56026-36-9, Methyl 6-(hydroxymethyl)nicotinate.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WO2006/122011; (2006); A2;,
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. 100866-13-5, name is 2-(Pyridin-4-yl)-1-(p-tolyl)ethanone, molecular formula is C14H13NO, 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. COA of Formula: C14H13NO

General procedure: To the intermediate ketone product (10 mmol) dissolved in MeOH (1 M) was addedhydroxylamine hydrochloride (1.04 g, 15 mmol, 1.5 equiv.) and NaOMe (0.81 g, 15 mmol,1.5 equiv.). This suspension is stirred at room temperature for 8 h until complete conversionof the substrate into the desired oxime is achieved (monitored by tlc and/or 1H-NMR).Aqueous extraction (3 × DCM/water) followed by drying the combined organic layers oversodium sulfate, filtration and evaporation to yield the oxime products as solids or oils thatsolidify upon storage.

With the rapid development of chemical substances, we look forward to future research findings about 100866-13-5.

Reference:
Article; Baumann, Marcus; Baxendale, Ian R.; Synlett; vol. 27; 1; (2016); p. 159 – 163;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5470-18-8, Adding some certain compound to certain chemical reactions, such as: 5470-18-8, name is 2-Chloro-3-nitropyridine,molecular formula is C5H3ClN2O2, 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.

A 5 L round bottom flask fitted with a condenser, mechanical stirrer and a nitrogen inlet was charged with 152.3 g (0.96 mol) of 2-chloro-3-nitropyridine and 1.65 L of 1,2-dimethoxyethane. The solution was degassed by bubbling nitrgen through the solution for 10 min and 56.7 g (0.49 mol, 0.05 equiv) of tetrakis (tliphenylphosphine)-palladium (0) was added. The mixture was degassed for an additional 45 min during which time the catalyst dissolved leaving a clear dark red solution. A degassed solution of 180.3 g (1.48 mol, 1.54 equiv) of phenylboronic acid in 800 [ML] of absolute ethanol was added followed by 1.65 L of degassed 2M aqueous sodium carbonate solution. The cloudy mixture was heated to reflux, and refluxed for 1.5 h. While at reflux a yellow suspension formed. The suspension was cooled to ambient temperature, diluted with 1 L of ethyl acetate, and filtered through [CELITE THE] cake was washed with 2 L of ethyl acetate and the filtrate washed with water (2 x 3 L), saturated sodium bicarbonate solution [(1 X 3] L), and saturated sodium chloride solution (1 x 3 L). The organic layer was dried with magnesium sulfate, filtered and the filtrate concentrated. The residue was dissolved in 1.5 L of ether, washed with 2.5N [NAOH] (2 x 500 mL) and brine (500 mL). The solution was dried with magnesium sulfate, filtered through 400 g of silica and the cake washed with additional ethyl acetate. The filtrate was concentrated to an oil which was chromatographed [5 kg Silica Gel 60,70-230 mesh, hexanes/ethyl acetate 80: 20 (12 L), 75: 25 (8 L), 70: 30 (11 L) and 60: 40 (7 L) ]. The product fractions were concentrated yielding 188.0 g (97% yield) of the title compound 2-phenyl-3-nitropyridine, as a pale yellow oil: [IH] NMR [(CDCL3)] 8 7.39-7. 49 (m, [4H),] 753-7.95 (m, 2H), 8.12 (m, 1H) 8.84 (m, [1H).] MS [(EI)] [M/Z] 200. Anal. Calcd for [CLLH8N204] : C, 66.00 ; H, 4.03 ; N, 13.99. Found: C, 66.19 ; H, 4.09 ; N, 13.98.

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. 5470-18-8, 2-Chloro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2004/29024; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1083181-26-3, 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.1083181-26-3, name is 3-Iodo-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5IN2, molecular weight is 244.03, as common compound, the synthetic route is as follows.

To a mixture of 3-iodo-1H-pyrrolo[3,2-b]pyridine (Intermediate 1), (350 mg) and potassium carbonate (791 mg) in DMF (8 mL) stirred at 0 C. under nitrogen was added 2-(4-(bromomethyl)-3-fluorophenyl)-6-methylpyridine hydrobromide (Intermediate 65), (620 mg). The reaction mixture was allowed to warm to rt and was stirred overnight. Water (50 mL) was added to the reaction mixture and the reaction mixture was extracted with EtOAc (100 mL). The organic phase was washed with brine (75 mL), dried (Na2SO4), filtered and evaporated under vacuum. The crude product was purified by column chromatography (silica) eluting with 28:72 EtOAc:hexanes to afford the title compound (580 mg) which was taken on as such. LCMS: m/z 444.11 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1083181-26-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem