Month: April 2022

Reference of 95652-80-5, 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 95652-80-5 as follows.

To a stirred solution of 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.To a suspension of the crude material including 12and NaOAc (3.78 g, 46.1 mmol) in the 1 : 1 mixture of n-BuOH and toluene (total 120 mL) was added Pd(dppf) Cl2 (1.12 g, 1.54 mmol) at room temperature. The resulting mixture was stirred under ordinary CO pressure (balloon) at 100C for 18 h. The reaction was quenched with saturated aqueous NH4Cl, filtered through a pad of Celite and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, n-hexane-EtOAc=2 : 1) to afford 13(4.75 g, 65% 2 steps) as a yellow oil.13: IR (film, cm-1): 2963, 2876, 1721, 1692, 1595, 1481, 1337, 1277, 1261, 1219, 1138, 1072, 1022; 1H-NMR (CDCl3, 500 MHz) delta: 10.39 (s, 1H), 8.18 (d, J=8.50 Hz, 1H), 6.94 (d, J=8.50 Hz, 1H), 4.44 (t, J=6.80 Hz, 2H), 4.06 (s, 3H), 1.83-1.76 (m, 2H), 1.54-1.45 (m, 2H), 0.99 (t, J=7.37 Hz, 3H); 13C-NMR (CDCl3, 125 MHz) delta: 189.1, 166.1, 165.2, 150.7, 138.6, 125.9, 114.1, 66.3, 54.5, 30.5, 19.2, 13.7; HR-MS (ESITOF): Calcd for C12H15NO4Na [(M+Na)+] 260.0893. Found 260.0891.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,95652-80-5, its application will become more common.

Reference:
Article; Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 723 – 732;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1187322-51-5, 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. 1187322-51-5, name is 6-Amino-5-iodonicotinonitrile. A new synthetic method of this compound is introduced below.

To the degassed mixture of 6-amino-5-(prop-l -yn-l-yl)pyridine-3-carbonitrile (329 mg, 1.34 mmol), bis'(triphenylphosphine)dichloropailadium(0) (95 mg, 0.134 mmol), copper (I) iodide (128 mg, 0.671 mmol) and triethylamine (976 mg, 1.34 mL, 9.64 mmol) in ahs. THF (18 mL) a propyn solution (3-4 % in THF; 13.2 mL) was added via septum at 0-5 C. The mixture was stirred for 30 minutes at 0-5 C, then for a further 18 hours at room temperature. The reaction was quenched by the addition of NFLCl solution. The solid was removed by filtration and the cake was washed with CH2CI2. The combined organic layer was dried with anhydrous NaiSOr, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica, eluted by 40 % EtOAc in cyclohexane to give 150 mg of the title compound as a yellow solid (71 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1187322-51-5, 6-Amino-5-iodonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; ELES, Janos; DUDASNE MOLNAR, Katalin; LEDNECZKI, Istvan; TAPOLCSANYI, Pal; HORVATH, Anita; NEMETHY, Zsolt; LEVAY, Gyoergy Istvan; (0 pag.)WO2020/12422; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 36953-37-4, 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 36953-37-4, name is 4-Bromopyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Example 26i 4-Bromo-2-(difluoromethoxy)pyridine 4-Bromopyridin-2(1H)-one (200 mg, 1.15 mmol) and sodium 2-chloro-2,2-difluoroacetate (210 mg, 1.38 mmol) were slurried in dry acetonitrile (8 mL). The mixture was refluxed overnight, allowed to cool to r.t. and directly extracted with pentane (3*5 mL). The combined organic phases were evaporated to give 219 mg (85% yield) of the title compound: 1H-NMR (500 MHz DMSO-d6) delta 8.18 (d, 1H), 7.70 (t, 1H), 7.56 (d, 1H), 7.50 (s, 1H); MS (CI+) m/z 226 224 [M+1]+

According to the analysis of related databases, 36953-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/125087; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1137-67-3, Adding some certain compound to certain chemical reactions, such as: 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole,molecular formula is C12H9N3, 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 1137-67-3.

, weighing 0.25g cobalt chloride hexahydrate,0.2 g of 2- (3-pyridyl) benzimidazole,0.2 g of 1,3-benzenedicarboxylic acid and 15 mL of water in a 50 mL flask,The flask was placed on a magnetic stirrer and stirred for 30 minutes.(2)The mixed homogeneous solution was transferred to a 25 mL autoclave.,The autoclave was placed in an oven,Heated from room temperature to 170 C at a rate of 1 C / min,At this temperature for 72h,And then to 5 / h rate down to room temperature,Solid-liquid separation is shown in Figure 1-3,The dinuclear cobalt complex shown in Figures 4-6,The yield was about 65%.

According to the analysis of related databases, 1137-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Heifei University; Zhang, Quanzheng; Cheng, Xuan; Ding, Dong; Chen, Ying; (13 pag.)CN103923126; (2016); B;,
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. 57963-08-3, name is 5,6-Dimethylpyridin-2-amine, the common compound, a new synthetic route is introduced below. Safety of 5,6-Dimethylpyridin-2-amine

Example 130 Synthesis of 5,6-dimethylpyridin-2-amine. To a solution of 5,6-dimethylpyridin-2-amine (1.0 g, 8.2 mmol) in DMF (10 mL) was added 1,3-dichloropropan-2-one (4.2 g, 32.8 mmol). The resulting mixture was stirred at 90 C. for 2 h. The reaction mixture was diluted with H2O (150 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash column chromatography to give 2-(chloromethyl)-5,6-dimethylimidazo[1,2-a]pyridine (1.0 g, yield: 63%). ESI-MS [M+H]+: 195.1.

The synthetic route of 57963-08-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 21427-61-2, 5-Chloro-2-hydroxy-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, 21427-61-2, blongs to pyridine-derivatives compound. Quality Control of 5-Chloro-2-hydroxy-3-nitropyridine

a) 3-amino-5-chloropyridin-2-ol A mixture of 5-chloro-3-nitropyridin-2-ol (30.0 g), iron (14.5 g), ammonium chloride (46.5 g) and ethanol/water (300 mL, 3/1, v/v) was stirred at 90 C. for 2 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (20.0 g). MS: [M+H]+ 145.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21427-61-2, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59942-87-9, 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. 59942-87-9, name is Pyrazolo[1,5-a]pyridin-2(1H)-one, molecular formula is C7H6N2O, 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.

A solution of pyrazolo[1,5-a]pyridin-2-ol (776 mg, 5.78 mmol), K2CO3 (2.4 g, 17.3 mmol), 1-bromo-4-chlorobutane (1.35 mL, 11.6 mmol) and sodium iodide (catalytic amount) in 20 mL of DMF was stirred for 18 h at room temperature. The resulting mixture was filtered, the solid washed with DMF and the organic filtrate concentrated. The residue was poured into diethyl ether and the generated precipitate filtered and discarded. The organic filtrate was washed with water and the organic layer dried (Na2SO4) and concentrated under vacuum to afford 1.35 g (quantitative) of brown oil.

According to the analysis of related databases, 59942-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratorios del. Dr. Esteve, S.A.; Diaz-Fernandez,Jose-Luis; Cuberes-Altisent,Mª Rosa; EP2631236; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59290-81-2, 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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid, molecular formula is C7H6N2O4, 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.

REFERENTIAL EXAMPLE 12 synthesis of N,N-diethyl 2-bromomethyl-5-nitronicotinamide To a solution of 0.6 g of 2-methyl-5-nitronicotinic acid and 3 ml of diethylamine in 100 ml of chloroform was added 20 g of phosphorus pentachloride and the resulting mixture was stirred at 60 C. for 3 hours. After cooling, the chloroform layer was separated, the solvent was distilled off under reduced pressure, the residue was mixed with water, neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was dried, concentrated and chromatographed over silica gel to give 0.4 g of the desired product as oil. Analysis for C11 H15 N3 O3: Calcd. (%): C, 55.68; H, 6.37; N, 17.71. Found (%): C, 55.57; H, 6.43; N, 17.56. To a solution of 0.4 g of N,N-diethyl-2-methyl-5-nitronicotinamide in 1.5 ml of acetic acid was added a solution of 0.27 g of bromine in 1.0 ml of acetic acid and the resulting mixture was stirred at 120 C. for 1.5 hours. The reaction mixture was poured into ice-water, made alkaline with sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off to give brown oily substance. This substance was chromatographed over silica gel to give 0.1 g of unreacted starting material and 0.28 g of N,N-diethyl 2-bromomethyl-5-nitronicotinamide. mp 62 – 64 C.

According to the analysis of related databases, 59290-81-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company Limited; US4053608; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1072-98-6 , The common heterocyclic compound, 1072-98-6, name is 2-Amino-5-chloropyridine, molecular formula is C5H5ClN2, 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.

Step 1. Ethyl 6-Chloroimidazo[1,2-a]pyridine-2-carboxylate To 2-amino-5-chloropyridine (Aldrich; 2.19 g) in dimethoxyethane (Aldrich; 25 mL) is added ethyl 2-bromopyruvate (Aldrich; 2.37 mL). After stirring overnight, the solid is collected and washed with diethyl ether. The solid is dried under reduced pressure at 45 C. and then is partitioned between dichloromethane and aqueous sodium bicarbonate. The organic phases are dried over sodium sulfate and concentrated to give 3.05 g of ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate. 1 H NMR (CDCl3) delta1.44, 4.46, 7.23, 7.64, 8.16, 8.21.

The synthetic route of 1072-98-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacia & Upjohn Company; US5912246; (1999); A;,
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.884494-82-0, name is 5-Fluoro-2-methoxynicotinic acid, molecular formula is C7H6FNO3, molecular weight is 171.13, as common compound, the synthetic route is as follows.Quality Control of 5-Fluoro-2-methoxynicotinic acid

PREPARATION 45-Fluoro-2,N-dimethoxy-N-methyl-nicotinamideTo a solution of 5-fluoro-2-methoxynicotinic acid (1 g, 5.8 mmol) in tetrahydrofuran (10 mL) was added 1 , 1 ‘-carbonyldiimidazole (1.4 g, 8.77 mmol, 1.5 eq.) portionwise over a 5 min period. The resulting solution was stirred at room temperature for 20 min before adding O, N-Dimethyl-hydroxylamine hydrochloride (0.63 g, 6.43 mmol, 1.1 eq.) and then stirred for a further 72 hr. The resulting mixture was then partitioned between ethyl acetate (30 mL) and 2M aqueous hydrochloric acid (30 mL). The organic phase was washed with 1 M aqueous sodium hydrogen carbonate (30 ml_), followed by brine (30 ml_) and then dried over magnesium sulphate. The resulting mixture was filtered and concentrated under reduced pressure to produce the title compound as a colourless oil (0.53 g, 43%).1H NMR (400 MHz, CDCI3): delta ppm 3.36 (br. s., 3 H) 3.55 (br. s., 3 H) 3.97 (s, 3 H) 7.33 – 7.44 (m, 1 H) 8.06 (d, J=2.73 Hz, 1 H).LRMS: APCI, m/z = 215 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-82-0, 5-Fluoro-2-methoxynicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem