Tag: M.W:100-200

Electric Literature of 100-26-5 ,Some common heterocyclic compound, 100-26-5, molecular formula is C7H5NO4, 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.

PREPARATION 1 dimethyl Pyridine-2,5-dicarboxylate To a stirred slurry of 2,5-pyridinedicarboxylic acid (2407 g; 14.4 mol) in methanol (8.0 liter) at -5 to -10C, thionylchloride (3430 g; 2.10 liters; 28.8 mol) was added dropwise while maintaining the temperature in the -5 to -10C range. After completing the addition, the reaction was allowed to warm to ambient temperature, and stirred for 18 hours. The resulting solution was concentrated in vacuo to a volume of 4 liters, and an equal volume of water was added. The PH of the well-stirred mixture was then adjusted to 10 with saturated aqueous sodium carbonate. Solids were removed by filtration. The organic layer of the filtrate was separated, washed with water (8 liters), and dried in vacuo to afford the title compound (2250 g; 80% yield) as an amorphous solid.

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. 100-26-5, 2,5-Pyridinedicarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; EP536173; (1995); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, molecular weight is 174, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4BrNO

Preparation 1022-Bromo- -difluoromethoxypyridineTo a solution of 2-bromo-3-pyridinol (1 .26 g, 7.23 mmol) in DMF (35 mL) and water (5 mL) was added sodium chlorodifluoroacetate (2.93 g, 18.1 mmol) followed by cesium carbonate (4.71 g, 14.5 mmol). The reaction was heated to 100 C for 36 hours before partitioning between EtOAc and water. The organic layer was collected, dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with EtOAc:heptane 1 :3 to afford the title compound as a colourless oil (570 mg, 35%).1H NMR (400 MHz; DMSO-d6): delta 7.15-7.55 (t, 1 H), 7.55 (m, 1 H), 7.80 (m, 1 H), 8.25 (m, 1 H).LCMS Rt = 1 .91 minutes MS m/z 226 [M79BrH]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6602-32-0, 2-Bromo-3-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan Daniel; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/7869; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128072-93-5, 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. 128072-93-5, name is Ethyl 5-chloropicolinate, molecular formula is C8H8ClNO2, 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.

Intermediate A-28A: tert-Butyl (2-(5-chloropicolinoyl)-6-methoxyphenyl)carbamate [0351] tert-butyl 2-methoxyphenylcarbamate (548 mg, 2.454 mmol) in ether (6 mL) under N2 was added t-BuLi (3.2 mL, 5.44 mmol). After stirring for 2.5 h, the reaction mixture was cooled to -78 C. To the reaction mixture was added a solution of ethyl 5-chloropicolinate (564.5 mg, 3.04 mmol) in ether (12 mL) dropwise via cannula over 5 min. The reaction mixture was stirred for 60 min, and then warmed to room temperature. After 1.5 h, to the reaction mixture was added H2O with vigorous stirring. The reaction mixture was diluted with EtOAc, and the organic phase was separated, washed with sat NaCl then dried (Na2SO4), filtered and concentrated to yield the product Intermediate A-29A (511.5 mg, 57.4% yield)) as a yellow solid: 1H NMR (400 MHz, chloroform-d) delta ppm 8.55 (1H, dd, J=2.3, 0.6 Hz), 8.08 (1H, dd, J=8.4, 0.7 Hz), 7.80 (1H, dd, J=8.4, 2.4Hz), 7.16-7.25 (2H, m), 7.06 (1H, dd, J=7.5, 2.2Hz), 6.90 (1H, s), 3.92 (3H, s), 1.28 (9H, s).

According to the analysis of related databases, 128072-93-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gavai, Ashvinikumar V.; DeLucca, George V.; O’Malley, Daniel; Gill, Patrice; Quesnelle, Claude A.; Fink, Brian E.; Zhao, Yufen; Lee, Francis Y.; US2014/87992; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 585-48-8, 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. 585-48-8, name is 2,6-Di-tert-butylpyridine. A new synthetic method of this compound is introduced below.

c Trifluoromethanesulfonic acid 2-amino-5-fluoro-6-furan-2-yl-pyrimidin-4-yl ester To a stirred suspension of 0.5 g (2.58 mmol) 2-amino-5-fluoro-6-furan-2-yl-3H-pyrimidin-4-one in 5 ml dichloromethane was added 1.16 ml (5.17 mmol) 2,6-di-tert-butylpyridine and the mixture was ultrasonicated for 30 minutes. 0.42 ml (2.55 mmol) triflic anhydride was then added dropwise at 0 C. with stirring and stirring continued at room temperature for 16 hours. The reaction mixture was then partitioned between water and dichloromethane and the organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was recrystallized from ether/hexane and the resulting crystals (2,6-di-tert-butylpyridinium triflate) were removed by filtration. The mother liquor was concentrated in vacuo to afford 0.84 g (99%) trifluoromethanesulfonic acid 2-amino-5-fluoro-6-furan-2-yl-pyrimidin-4-yl ester as a brown crystalline solid. ES-MS m/e (%): 326 ([M-H]-, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,585-48-8, its application will become more common.

Reference:
Patent; Borroni, Edilio Maurizio; Huber-Trottmann, Gerda; Kilpatrick, Gavin John; Norcross, Roger David; US2001/27196; (2001); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14667-47-1 ,Some common heterocyclic compound, 14667-47-1, molecular formula is C7H8N2O2, 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 solution of 2-amino-3-nicotinic acid methyl ester (4 g, 26 mmol) in a mixture of concentrated HN03 (2.8 mL) and H2S04 (10 mL) was stirred for 45 min at 0 C, followed by room temperature for 19 h, and at 70 C for 4 h. The reaction mixture was cooled to 0 C and a saturated aqueous solution of NaHC03 (40 mL) was added till basic (pH 8). Extraction with EtOAc (3X40 mL), filtered and concentration of the combined organics afforded the title compound (3.5 g, 68%) which was used in the next step without further purification. 1H NMR (DMSO-cfe, 400 MHz): delta 9.05 (1 H, d, J = 2.8 Hz), 8.69 (1 H, d, J = 2.8 Hz), 8.64 (1 H brs), 8.15 (1 H, brs), 3.88 (3H, s). MS: mlz 198 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14667-47-1, its application will become more common.

Reference:
Patent; UNIVERSITY OF DUNDEE; MEDIVIR AB; CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS; SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE; SYNGENE INTERNATIONAL LIMITED PLC; KAHNBERG, Pia; JOHANSSON, Nils-Gunnar; GILBERT, Ian; HAMPTON, Shahienaz; HARRISON, Justin; SARKAR, Sandipan; GONZALES, Dolores; WO2015/189595; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 2402-77-9, 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 2402-77-9 as follows.

2,3-Dichloro-isonicotinic acid[00195] To a solution of diisopropylamine (7.0 niL, 50 mmol) in anhydrous THF (100 rnL) at -25C was added a 1.6M solution of nBuLi in hexanes (31 rnL, 50 mmol) dropwise under an inert atmosphere. The reaction mixture was then cooled to -78C and 2,3- dichloropyridine was added. The reaction mixture was stirred at -78C for 3 hours, then poured onto solid carbon dioxide and aged for 18 hours at room temperature. The mixture was diluted with water (100 mL) and washed with diethyl ether (3 x 40 mL) then cooled to 00C, acidified with concentrated HCl (ca. 5 mL) and extracted with diethyl ether (3 x 50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to give the title compound as a white solid (7.7 g, 80%). 1H NMR (d6-DMSO, 400MHz) 8.49 (d, J = 5.0 Hz, IH), 7.72 (d, J = 5.0 Hz, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2402-77-9, its application will become more common.

Reference:
Patent; GENENTECH, INC.; WO2009/85980; (2009); A1;,
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. 16063-70-0, name is 2,3,5-Trichloropyridine, the common compound, a new synthetic route is introduced below. Formula: C5H2Cl3N

To a solution of tert- butyl N-(2-amino-5-fluoro-phenyl)-N-methyl-carbamate (80 g, 333 mmol, compound A 1.4) and 2,3,5 -trichloropyridine (66.8 g, 366 mmol, CAS: 16063-70-0) in dioxane (2 L) were added cesium carbonate (217 g, 666 mmol), palladium(II) acetate (3.74 g, 16.7 mmol), and BINAP ( 20.7 g, 33.3 mmol, CAS: 98327-87-8). The reaction mixture was stirred at 120 C for 16 h under nitrogen atmosphere. After the reaction mixture was cooled back to room temperature, it was diluted with EtOAc (800 mL). The precipitate was removed by filtration and the filtrate was concentrated in vacuo, and the crude product was purified by silica gel flash chromatography (0.2% to 5% EtOAc in petroleum ether) to give intermediate fe/7-butyl N-[2-[(3,5-dichloro-2-pyridyl)amino]-5-fluoro-phenyl]-N-methyl-carbamate (75 g, 58% yield) as a white solid. MS (ESI): 390.1 ([{37C1}M+H]+), 388.1 ([{37C1+35C1 }M+H]+), 386.1 (0192) ([{35C1}M+H]+).

The synthetic route of 16063-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; SHEN, Hong; TAN, Xuefei; ZHOU, Chengang; ZHOU, Mingwei; HU, Yimin; SHI, Houguang; DEY, Fabian; LIU, Yongqiang; DING, Xiao; (86 pag.)WO2020/104436; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55676-21-6, 1-(2-Chloropyridin-3-yl)ethanone, 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, 55676-21-6, blongs to pyridine-derivatives compound. Product Details of 55676-21-6

KOH (0.5 N MeOH, 6.0 mL, 3.0 mmol) was added to a solution of the compound 6 (467 mg, 3.0 mmol) prepared in Example 1 and 2-methoxybenzaldehyde (408 mg, 3.0 mmol) in THF The reaction was stopped by adding 0.5 N HCl (6 mL) to the mixed light yellow solution at 0 ° C and mixing at 0 ° C to room temperature for 3 hours. After evaporation of the solvent from this solution, the mixture was taken up in saturated NaHCO3 solution (30 mL) and extracted three times with dichloromethane (20 mL). The concentrated residue was purified by silica gel column chromatography using 30percent EtOAc / n-hexane as the extraction solvent to give compound 7l (673 mg, 82percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55676-21-6, its application will become more common.

Reference:
Patent; Duksung Women’s University Industry-Academic Cooperation Foundation; Jae, In Lee; (15 pag.)KR101766414; (2017); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69008-70-4, N,N-Dipropylpyridin-4-amine, 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, SDS of cas: 69008-70-4, blongs to pyridine-derivatives compound. SDS of cas: 69008-70-4

To a solution of 4-dipropylaminopyridine (1.16 g, 6.50 mmol) in benzonitrile (2.0 mL) was added 1-iodoadamantane (2.04 g, 7.80 mmol).Was added and stirred at 145 C. for 60 hours. After cooling to room temperature,The reaction solution was purified by silica column chromatography (chloroform / methanol),Brown solid 1- (1-adamantyl) -4-dipropylaminopyridinium iodide(0.717 g, yield 25%) was obtained.

The synthetic route of 69008-70-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ???????????????; ???????; Araki Keisuke; Nakamura Maki Tsukasa; Yoshioka Masato; Naranoki Yuusuke; (35 pag.)JP2019/210213; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 115170-40-6, 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 115170-40-6 as follows.

To a solution of 5-bromo-2,3-dihydro-1 H-pyrrolo(2,3-b)pyridine (CAS Number 1 15170-40-6; 0.300 g, 1 .507 mmol) in 1 ,4-dioxane:water (1 : 1 , 8 ml) were added phenylboronic acid (0.294 g, 2.412 mmol) and K2CO3 (0.624 g, 4.52 mmol) at rt. The reaction mixture was degassed for 30min before addition of Pd(PPh3)4 (0.087 g, 0.075 mmol) thenheated at 80C for 1 h. The reaction was cooled to rt, poured into water (100 ml) and extracted with EtOAc (3 x 50 ml). The combined organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure yielding 5-phenyl-2,3-dihydro-1 H-pyrrolo[2,3-b]pyridine (0.440 g, 2.24 mmol). MS: ES+ 197.1 .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115170-40-6, its application will become more common.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (167 pag.)WO2018/65768; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem