Month: April 2022

Synthetic Route of 947249-27-6 , The common heterocyclic compound, 947249-27-6, name is 2-Bromo-3-(difluoromethoxy)pyridine, molecular formula is C6H4BrF2NO, 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 1032-Cvclopropyl-3-(difluoromethoxy)pyridineCyclopropylboronic acid (383 mg, 4.5 mmol) and potassium phosphate tribasic (1 .89g, 8.9 mmol) were added to a solution of 2-bromo-3-difluoromethoxypyridine (Preparation 102, 570 mg, 2.5 mmol). The mixture was heated to 80 C and degassed thoroughly by bubbling nitrogen through the mixture. After 30 minutes, the reaction was heated to 95 C and tricyclohexylphosphine (84 mg, 0.30 mmol) was added followed by palladium acetate (32 mg, 0.14 mmol). The reaction was stirred at 95 C for 18 hours then cooled to room temperature. The mixture was filtered through arbocel, washing with EtOAc and the filtrate concentrated in vacuo. The residue was then purified by flash column chromatography eluting with EtOAc:heptane 1 :5 to afford the title compound as a colourless oil (273 mg, 58%).1H NMR (400 MHz; DMSO-d6): delta 0.95 (m, 4H), 2.30 (m, 1 H), 7.05-7.42 (t, 1 H), 7.15 (m,1 H), 7.5 (m, 1 H), 8.25 (m, 1 H).LCMS Rt = 2.09 minutes MS m/z 186 [MH]+

The synthetic route of 947249-27-6 has been constantly updated, and we look forward to future research findings.

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

Related Products of 947249-13-0, 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.947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, molecular formula is C6H5BrF2N2O, molecular weight is 239.02, as common compound, the synthetic route is as follows.

A mixture of 5-bromo-3-(difluoromethoxy)pyridine-2-amine (88 mg, 0.37 mmol), bis(pinacolato)diboron (102 mg, 0.40 mmol), potassium acetate (0.215 mg, 2.2 mmol), and Pd(dppf)-CH2Cl2 (30 mg, 0.037 mmol) in dry dioxane (2.0 mL) was sparged with argon, and heated at 120 C. for 30 min. After cooling to rt, the reaction mixture was centrifuged and the supernatant decanted, and used in the next step without further purification: LCMS (m/z, MH+, boronic acid): 205.0, tR=0.27 min.

Statistics shows that 947249-13-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-(difluoromethoxy)pyridin-2-amine.

Reference:
Patent; Huang, Zilin; Jin, Jeff; Machajewski, Timothy; Antonios-McCrea, William R.; McKenna, Maureen; Poon, Daniel; Renhowe, Paul A.; Sendzik, Martin; Shafer, Cynthia; Smith, Aaron; Xu, Yongjin; Zhang, Qiong; Chen, Zheng; US2013/210818; (2013); 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 880870-13-3

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mE) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, succes30 sively. The resulting suspension was stirred at 95 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to providethe crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate/hexanes to afford theproduct.?H NMR (500 MHz, DMSO-d5), oe 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); EC/MS (M+1)=169.

The synthetic route of 880870-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Walsh, Shawn P.; Pasternak, Alexander; Shi, Zhi-Cai; Cato, Brian; Kim, Esther Y.; (32 pag.)US9493474; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1019021-85-2, 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 1019021-85-2, name is 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a stirring suspension of 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (24b) (150 mg, 0.833 mmol) in anhydrous dichloromethane (3 ml_) at 0 C under argon was added dropwise oxalyl chloride (74 muIota_, 0.874 mmol). Then, a drop of anhydrous DMF was added and the reaction mixture was stirred at 0 C for 1 .5 hours. The solvent was concentrated and the crude solid was added to a stirring solution of methyl (3-(3-amino- 4-methylphenyl)-1 ,2,4-oxadiazol-5-yl)methylcarbamate (155) (120 mg, 0.416 mmol) in anhydrous pyridine (3 mL) at 0 C. The reaction was stirred at room temperature under argon for 20 minutes. The solvent was concentrated and the crude product was purified by silica chromatography to give methyl (3-(3-(6-fluoroimidazo[1 ,2-a]pyridine-3- carboxamido)-4-methylphenyl)-1 ,2,4-oxadiazol-5-yl)methylcarbamate (F167). 1 H NMR (400MHz, c/6-DMSO) delta 10.12 (s, 1 H), 9.48 – 9.46 (m, 1 H), 8.63 (s, 1 H), 8.07 (t, J = 5.6 Hz, 1 H), 8.06 (d, J = 1 .6 Hz, 1 H), 7.90 – 7.86 (m , 1 H), 7.82 (dd, J = 2.0, 8.0 Hz, 1 H),7.67 – 7.62 (m, 1 H), 7.50 (d, J = 8.0 Hz, 1 H), 4.57 (d, J = 6.0 Hz, 2H), 3.59 (s, 3H), 2.36 (s, 3H). MS m/z 425.39 (M+1 )+.

According to the analysis of related databases, 1019021-85-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153747-97-8, 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, 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.

Step II: tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylate (Intermediate 1-XIII) A mixture of 1-11 (4.30 g, 12.57 mmol), bis(pinacolato)diboron (3.82 g, 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1-bis(diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100 C. for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate (50 mL*3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50% EtOAc in hexanes to give the desired product Intermediate 1-XIII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98%) as a yellow solid; LCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M++1].

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; BHOSALE, Sandeep; NAIK, Keshav; SALUNKHE, Videsh; MUNOT, Yogesh; BHUNIYA, Debnath; (132 pag.)US2017/8885; (2017); A1;,
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.89026-78-8, name is 6-Chloro-N-methylpyridin-2-amine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.Formula: C6H7ClN2

2-Chloro-N-(6-chloropyridin-2-yl)-N-methyl-pyrimidin-4-amine used as starting material was made as follows: NaHMDS (1.5 ml, 1.5 mmol, IN in THF) was added dropwise to a mixture of 2-chloro-6- methylaminopyridine (142 mg, 1 mmol, German Patent, DE3318560, p 9) and 2,4- dichloropyrimidine (222 mg, 1.5 mmol) in THF (20 ml) cooled at -200C. The mixture was stirred at -200C for 2 hours. Acetic acid (a few drops) were added and the mixture was concentrated. The mixture was taken in DCM, filtered and concentrated. The residue was purified by chromatography on silica gel (eluant: 40% to 50% ethyl acetate in petroleum ether) to give 2-chloro-N-(6-chloropyridin-2-yl)-N-methyl-pyrimidin-4-amine (86 mg, 34%). NMR Spectrum: (CDCl3) 3.61 (s, 3H), 6.93 (d, IH), 7.18 (d, IH), 7.28 (m, IH), 7.72 (t, IH), 8.17 (d, IH); Mass spectrum: MH+ 255.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89026-78-8, 6-Chloro-N-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/10794; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1211523-71-5, Adding some certain compound to certain chemical reactions, such as: 1211523-71-5, name is 2-(2-Bromopyridin-3-yl)acetonitrile,molecular formula is C7H5BrN2, 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 1211523-71-5.

To 0C2-(2-Bromopyridin-3-yl)acetonitrile (2.21 g, 11.21 mmol) in DMF (20 mL)Sodium hydride (60% mineral oil dispersion, 1.12 g, 28.03 mmol) was added portionwise to the solution.The reaction system was warmed to 60 C and stirred for 1.5 h.tert-Butyl bis(2-chloroethyl)carbamate (3.26 g, 13.46 mmol) was added to the mixture and stirred at 60 C for 2 h.After cooling to RT, the reaction was quenched with brine (50 mL).Extract with EA (3 x 100 mL). The combined organic phases were washed with brine (3×40 mL).Dry over anhydrous Na2SO4, filtered and evaporated.The residue was purified by silica gel chromatography eluting with EtOAc:EtOAc:4-(2-Bromopyridin-3-yl)-4-cyanopiperidine-1-carboxylic acid tert-butyl ester (1.56 g) was obtained.

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. 1211523-71-5, 2-(2-Bromopyridin-3-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Jiakesi Drug Discovery Co., Ltd.; Ma Cunbo; Gao Panliang; Hu Shaojing; Xu Zilong; Han Huifeng; Wu Xinping; Kang Di; Long Wei; (147 pag.)CN110143949; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 90145-48-5, Adding some certain compound to certain chemical reactions, such as: 90145-48-5, name is 5-Bromopyridine-2-carboxamide,molecular formula is C6H5BrN2O, 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 90145-48-5.

Step 1 5-Triotabutylstannanyl-pyriotadiotane-2-carboxyhc acid amide[00294] A degassed mixture of 5-bromo-py?dme-2-carboxylic acid (0 2g, lmmol), t?butyltm(1 16g, 2mmol) and PdCl2(PPh3)2 (0 07g, 0 lmmol) in DMF (4mL) is stirred at 1150C Additional 20% of PdCl2(PPh3)2 (0 14g, 0 2mmol) is added and the reaction stirred for 24 hours The reaction mixture is partitioned between EtOAc and water, the organic layer is washed with water (4x), d?ed over MgSO4, filtered and concentrated in vacuo The crude is purified by silica gel column chromatography eluting with 9 1 petroleum ether-ethyl acetate to afford the title compound (O 132 mg, 32%)

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. 90145-48-5, 5-Bromopyridine-2-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 696-42-4, 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.696-42-4, name is 5-Fluoronicotinonitrile, molecular formula is C6H3FN2, molecular weight is 122.0998, as common compound, the synthetic route is as follows.

To a stirred solution of 5-fluoropyridine-3-carbonitrile (2.0 g, 16.38 mmol) in methanol (20 mL) at RT was added NaOMe (88mg, 1.64 mmol) and the reaction stirred at RT overnight. Ammonium chloride (1 .40g, 26.21 mmol) was added in a single portion and the reaction mixture stirred overnight at RT. The reaction mixture was filtered and the filtrate concentrated to dryness under reduced pressure. The residue was suspended in EtOH (50 mL) and then heated at reflux. The undissolved solid was filtered off and the filtrate concentrated to 1/3 of its volume and then left to stand at RT. The resultant crystals were filtered off, washed with EtOH and air-dried to give the desired product (2.1 1 g, 73%) as white crystals. 1H NMR (400 MHz, d6-DMSO) o 8.93 (d, 1 H), 8.88 (s, 1 H), 8.29-8.23 (m, 1 H).

Statistics shows that 696-42-4 is playing an increasingly important role. we look forward to future research findings about 5-Fluoronicotinonitrile.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WAILES, Jeffrey, Steven; BRIGGS, Emma; CARTER, Neil, Brian; MORRIS, Melloney; TATE, Joseph, Andrew; (61 pag.)WO2019/57722; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15103-48-7 ,Some common heterocyclic compound, 15103-48-7, molecular formula is C5H5NO3S, 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.

1 g of the compound Slic-CJH-5 prepared in the fourth step of Example 2,And 200mgof2-pyridine sulfonic acid and 530 mg of anhydrous sodium carbonate were dispersed in 40 ml of ethylene glycol ether,Under nitrogen protection,The temperature was refluxed for 12 hours,Cooled to room temperature, diluted with dichloromethane, washed three times with water, dried in organic phase,Filtered, the filtrate was concentrated under reduced pressure,The residue was purified by silica gel column and recrystallized from ether-petroleum ether,To obtain 460 mg of the compound Slic-CJH-DB011-VII02,Yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15103-48-7, its application will become more common.

Reference:
Patent; Shijiazhuang Chengzhi Yonghua Xianshi Material Limited Company; Cao, Jianhua; Pang, Hui; Huang, Hongliang; Hua, Ruimao; (36 pag.)CN103896990; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem