Day: April 12, 2022

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

Adding a certain compound to certain chemical reactions, such as: 886364-94-9, 5-Bromo-4-methylpicolinaldehyde, 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, COA of Formula: C7H6BrNO, blongs to pyridine-derivatives compound. COA of Formula: C7H6BrNO

To a solution of ethylene glycol (310 mg, 5.00 mmol, 280 pL, 2.00 equiv), 5-bromo-4- methyl-pyridine-2-carbaldehyde (500 mg, 2.50 mmol, 1.00 equiv) in toluene (20.0 mL) was added / oluenesul fonic acid (47.6 mg, 250 pmol, 0.10 equiv). The mixture was stirred at 110 C for 12 h and was subsequently concentrated in vacuo to give a residue. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate = 1/0 to 5: 1) to afford 5-bromo- 2-(l, 3-dioxolan-2-yl)-4-methylpyridine (320 mg, 1.24 mmol, 49.6% yield) as a colorless oil. 1H NMR (400MHz, CDCI3) d = 8.64 (s, 1H), 7.42 (s, 1H), 5.80 (s, 1H), 4.19 – 4.14 (m, 2H), 4.10 – 4.05 (m, 2H), 2.42 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886364-94-9, 5-Bromo-4-methylpicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
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. 1073159-75-7, name is N-(3-(Aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide acetate, molecular formula is C10H17N3O4S, 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. name: N-(3-(Aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide acetate

Step 2. A solution of tert-butanol (20.0 mL), DCE (20.0 mL) and DIEA (3.13 mL, 18.0 mmol) was treated with C8 (5.60 g, 15.0 mmol) and B5 (5.02 g, 15.0 mmol), and the resulting mixture was stirred at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was cooled to 25 C. and concentrated. The resultant residue was partitioned between EtOAc and 1 N sodium hydroxide, and the organic phase was collected. The aqueous layer was extracted with EtOAc, and the combined organic phases were dried over MgSO4 and filtered. The resultant filtrate was concentrated under reduced pressure, and the resultant residue was triturated with hot EtOAc to provide 9 as a white solid. Yield: 7.83 grams, 95%. LC/MS (standard) 250=3.0 min., m/z 553.6 (MH+). HPLC (FAK1) 250=8.14 min. 1H NMR (d6-DMSO) : 9.75 (bs, 1H), 8.44 (d, J=5.2 Hz., 1H), 8.29 (s, 1H), 8.05 (bs, 1H), 7.82 (d, J=7.8 Hz., 1H), 7.60 (t, J=5.7 Hz., 1H), 7.44-7.40 (m, 2H), 7.17 (t, J=5.7 Hz, 1H), 4.82 (d, J=5.7 Hz., 2H), 3.16 (s, 3H), 3.13 (s, 3H), 1.51 (s, 9H) ppm. FAK IC50: 0.0006 muM

With the rapid development of chemical substances, we look forward to future research findings about 1073159-75-7.

Reference:
Patent; Pfizer Inc.; US2009/54395; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156072-84-3 ,Some common heterocyclic compound, 156072-84-3, molecular formula is C7H5ClN2, 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 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH (110 mL of 5 N solution, 550 mmol). The resulting mixture was refluxed at 90 C. for 18 h. After cooling to RT, the reaction mixture was concentrated. The residue was diluted with water and the pH of the solution was adjusted to 4 by addition of 5 N HCl. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2×). The aqueous layer was again acidified with 5 N HCl to pH 4 and extracted with EtOAc (2×). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a high vac oven at 40 C. for 12 h to give 5-chloro-3-methylpicolinic acid (268) (24.1 g, 140 mmol, 89% yield). LC/MS (ESI+) m/z=172.0 (M+H)+. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 11.29 (br. s., 1H), 8.41 (d, J=1.76 Hz, 1H), 7.73 (d, J=1.76 Hz, 1H), 2.75 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156072-84-3, its application will become more common.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); 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.135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.category: pyridine-derivatives

General procedure: Reference Example 24 6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile [0267] To a solution of 5-methoxy-2-phenyl-1H-indole (200 mg) in N,N-dimethylformamide (5 mL) was added sodium hydride (dispersed in liquid paraffin, 50% or more, 45 mg) under ice-cooling. This mixture was stirred for 30 minutes at room temperature. Subsequently, 6-chloromethylpyridine-2-carbonitrile (216 mg) was added thereto, followed by stirring at 80C overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (228 mg). [0268] 1H-NMR (DMSO-d6) delta ppm: 3.77 (3H, s), 5.55 (2H, s), 6.55-6.65 (1H, m), 6.77 (1H, dd, J = 2.4, 8.8 Hz), 6.91 (1H, dd, J = 1.5, 7.4 Hz), 7.13 (1H, d, J = 2.4 Hz), 7.26 (1H, d, J = 8.8 Hz), 7.35-7.55 (5H, m), 7.85-7.95 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Kyorin Pharmaceutical Co., Ltd.; TATANI, Kazuya; KONDO, Atsushi; KONDO, Tatsuhiro; KAWAMURA, Naohiro; SETO. Shigeki; KOHNO, Yasushi; EP2669271; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem