Day: April 20, 2022

Adding a certain compound to certain chemical reactions, such as: 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, 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, 1026796-81-5, blongs to pyridine-derivatives compound. HPLC of Formula: C7H7BrN2O

00569] Step 1: N-(4-bromopyridin-2-yl)-N-(4-methoxybenzyl)acetamide [00570] To a 20 mL vial charged with Sodium hydride (0.196 g, 7.76 mmol) was added dry N,N- Dimethylformamide (5.0 mL, 64 mmol), cooled with ice bath. N-(4-bromopyridin-2-yl)acetamide (1.50 g, 7.00 mmol) was added portionwise in ~ 3 min. The suspension was stirred at the same temperature for 15 min and turned into a clear solution. 4-methoxybenzyl bromide (1.55 g, 7.70 mmol) was added dropwise with a syringe and rinsed down with dry N,N-Dimethylformamide (2.0 mL, 26 mmol). The MPI09-013P1RNWOM PCT FILING mixture was stirred at r.t. for 17 hours. The mixture was poured into ice chilled saturated NaHCO3 (80 mL), extracted with EtOAc (2 x 100 mL), washed with water, brine, dried over anhydrous Na2SO4, filtered, evaporated in rotavpor to give a crude. Chromatograph using EtOAc/hexane (1/9 to 7/3) gave an oily product (1.80 g, yield 76.7%). LCMS: (AA) ES+, 335, 337. 1H NMR (400 MHz, d, -chloroform) delta:8.28-8.30 (d, J = 5.27 Hz, IH), 7.43 (s, IH), 7.31-7.33 (dd, J = 5.52, 1.51 Hz, IH), 7.13-7.15 (d, J = 8.78Hz, 2H), 6.80-6.82 (d, J = 8.78 Hz, 2H), 5.05 (s, 2H), 3.77 (s, 3H), 2.12 (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,1026796-81-5, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANNO, Hiroshi; HIROSE, Masaaki; KURASAWA, Osamu; LANGSTON, Steven, P.; MIZUTANI, Hirotake; SHI, Zhan; VISIERS, Irache; VOS, Tricia, J.; VYSKOCIL, Stepan; WO2010/90716; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133928-73-1, 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. 133928-73-1, name is 2-Chloro-3-methyl-4-pyridinecarboxylic Acid. A new synthetic method of this compound is introduced below.

[01652] Step 4: Synthesis of methyl 2-chl hylpyridine-4-carboxylate[01653] To a stirred solution of 2-chloro-3-methylpyridine-4-carboxylic acid (780 mg, 4.5 mmol) in anhydrous DMF (5.0 ml), was added potassium carbonate (1 .25 g, 9.1 mmol), followed by methyl iodide (0.42 ml, 6.8 mmol) dropwise. A further 4 ml of DMF was added and the reaction mixture was stirred at room temperature under nitrogen for 18.5 hours. The solvent was removed in-vacuo and the residue was then partitioned between CI b b (20 ml) and water (20 ml). The layers were separated and the aqueous layer was extracted with CH2C12 (3 x 15 ml). The combined organic layers were washed with water (2 x 30 ml), brine (40 ml), dried (MgS0 ), filtered and concentrated in-vacuo. The residue was purified by column chromatography (l Og SNAP cartridge, Isolera, 0-6% ethyl acetate:heptanes) to give the title compound (591 mg, 59%) as a colourless oil. LC-MS 84%, m/z = 185.9, 1 87.9; NMR (500 MHz, Chloroform-d) delta ppm 8.33 (d, J=5.04 Hz, 1 H) 7.54 (d, J=5.04 Hz, 1 H) 3.95 (s, 3 H) 2.60 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,133928-73-1, 2-Chloro-3-methyl-4-pyridinecarboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, the common compound, a new synthetic route is introduced below. Computed Properties of C13H17NO4

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

The synthetic route of 1149-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75073-11-9, 5-Iodo-6-methylpyridin-2-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, Recommanded Product: 75073-11-9, blongs to pyridine-derivatives compound. Recommanded Product: 75073-11-9

5-Iodo-6-methylpyridin-2-ylamine (2.00 g, 8.55 mmol), IH-[1, 2,4] triazole (590 mg, 8.55 mmol), CuI (80.0 mg, 430 mumol), K3PO4 (3.80 g, 18.0 mmol) and N,N-dimethylethane- 1,2-diamine (190 muL, 1.71 mmol) in DMF (20 mL) were heated in the microwave at 15O0C for 9 h. The reaction mixture was cooled to ambient temperature and diluted with H2O and EtOAc. The aqueous layer was extracted with EtOAc (6x) and the combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (EtOAc-IH; 1:9) afforded the title compound: RT = 0.26 min; mlz (ES+) = 175.97 [M + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75073-11-9, 5-Iodo-6-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; PROSIDION LIMITED; BERTRAM, Lisa, Sarah; FYFE, Matthew, Colin, Thor; WO2010/4345; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1155847-42-9, Adding some certain compound to certain chemical reactions, such as: 1155847-42-9, name is 2-Bromo-4-chloro-3-fluoropyridine,molecular formula is C5H2BrClFN, 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 1155847-42-9.

[00409] Intermediate 4 IB. 4-Chloro-3-fluoro-2-hydrazinylpyridine, 2HC1: In microwave vial was added toluene (3 mL) and purged with N2 for 5 min. tert-Butyl carbazate (128 mg, 0.950 mmol), Intermediate 101 A (200 mg, 0.950 mmol), Cs2C03 (310 mg, 0.950 mmol), DPPF (20 mg, 0.036 mmol), and Pd2(dba)3 (25 mg, 0.027 mmol) were added sequentially into the solution. The sealed tube was heated at 100 C for 12 h. The reaction was diluted with brine, and extracted with EtOAc (2x). The combined organic layer was concentrated in vacuo, yielding oily residue, which was purified by silica gel chromatography to provide tert-butyl 2-(4-chloro-3-fluoropyridin-2- yl)hydrazinecarboxylate (41 mg, 16%) as orange solid. MS(ESI) m/z: 262.1 (M+H) . To the solid was added EtOH (1 mL) and 4 N HCl in dioxane (4 mL) and the reaction mixture was stirred for 2 h at rt. The mixture was concentrated to dryness to the desired product. MS(ESI) m/z: 162.1 (M+H)+.

According to the analysis of related databases, 1155847-42-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 824-51-1, Adding some certain compound to certain chemical reactions, such as: 824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine,molecular formula is C8H8N2, 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 824-51-1.

To a solution of 6-methyl-1H-pyrrolo[2,3-b]pyridine (500 mg) in dichloroethane (6 mL) were added aluminumchloride (1.09 g) and acetyl chloride (0.40 mL), and then the mixture was stirred at room temperature for 1.5hours. The reaction solution was poured into aqueous saturated sodium hydrogen carbonate solution, andextracted with chloroform. The organic layer was washed with saturated saline, dried over magnesium sulfate,and then concentrated under reduced pressure. The resulting residue was triturated with isopropyl ether to give1-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone [REx(8-1)] (481 mg) as a yellow powder.APCI-MS m/z: 175[M+H]+.

According to the analysis of related databases, 824-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; Shanghai Pharmaceuticals Holding Co., Ltd.; IIJIMA, Toru; SUGAMA, Hiroshi; KAWAGUCHI, Takayuki; SHEN, Jingkang; XIA, Guangxin; XIE, Jianshu; EP2687518; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75893-75-3, 6-Cyclopropylnicotinic acid, 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, 75893-75-3, blongs to pyridine-derivatives compound. Formula: C9H9NO2

Step-6: Synthesis of N-[3-bromo-2-[[tert-butyI(dimethyl)siIyl]oxymethyl]phenyl]-6- cyclopropyl-pyridine-3-carboxamide: To a solution of 6-cyclopropylpyridine-3-carboxylic acid (0.5 g, 3.06 mmol), 3-bromo-2-[[tert- butyl(dimethyl)silyl]oxymethyl]aniline (1.16 g, 3.67 mmol) and HOBt (0.495 g, 3.67 mmol) in DCM (15 mL) was added NMM (0.5 mL, 4-59 mmol) and EDCI.HCl (0.876 g, 4.59 mmol). The reaction mixture was stirred at room temperature for 16 h. After completion of the reaction (as indicated by TLC), water (10 mL) was added to it and extraction was carried out using DCM (50 mL x 2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified using column chromatography (Si02, 10% ethyl acetate in hexanes) to afford title compound (0.5 g, 35%). LCMS: m/z 461.2 (M + 1)+. NMR (400 MHz, CDC13) delta 0.15 (s, 6H), 0.87 (s, 9H), 1.05-1.10 (m, 2H), 1.1 1-1.51 (m, 2H), 2.06-2.16 (m, 1H), 5.1 1 (s, 2H), 7.19-7.23 (aromatics, 2H), 7.33 (d, J = 8.0 Hz, 1H), 8.03 (dd, J = 8.0, 2.0 Hz, 1H), 8.33 (d, J = 8.0 Hz, 1H), 8.99 (d, J = 2.0 Hz, lH), 9.99 (s, lH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75893-75-3, its application will become more common.

Reference:
Patent; ADVINUS THERAPEUTICS LIMITED; THAKKAR, Mahesh; KOUL, Summon; BHUNIYA, Debnath; SINGH, Umesh; WO2013/157021; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 372198-69-1, 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 372198-69-1, name is Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl 6-bromoimidazo[l,2-a]pyridine-3-carboxylate (180 mg, 0.67 mmol) THF (2 mL) and methanol (2 mL) was added LiOH (56 mg 1.34 mmol) in water (2 mL) and stirred at 60 C overnight. After removal of volatile solvent by rotary evaporation, the mixture was diluted with water and acidified to pH 4 with an aqueous solution of IN HC1. The resulting precipitate was collected by filtration, washed with water, and dried under vacuum to afford the title compound (108 mg, 67%). This intermediate was used in subsequent reactions without further purification. LC-MS: single peak at 254 nm, MH+ calcd. for C8H6BrN202: 241, obtained: 241.

According to the analysis of related databases, 372198-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1092286-30-0, 5-Chloro-2-methyl-3-pyridinecarboxylic acid, 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, Recommanded Product: 1092286-30-0, blongs to pyridine-derivatives compound. Recommanded Product: 1092286-30-0

5-Chloro-2-methylnicotinoyl chloride5-Chloro-2-methyl-nicotinic acid (4.15 g, 24.2 mmol) was placed in a flask with DCM (100 ml) and oxalyl chloride (3.68 g, 29 mmol). DMF (200muIota) was added and the reaction mixture was stirred at RT for 1 hour (gas evolution). The mixture was filtered and the solvent was removed in vacuo to afford the title product which was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1092286-30-0, 5-Chloro-2-methyl-3-pyridinecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BEATTIE, David; BRUCE, Ian; COLSON, Anny-Odile; CULSHAW, Andrew James; SHARP, Thomas; WO2011/95450; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72093-04-0, 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. 72093-04-0, name is 3-Chloro-4-methylpyridine. A new synthetic method of this compound is introduced below.

EXAMPLE 32 Compound CM A solution of diisopropylamine (1.23 mL) in dry tetrahydrofuran (15 mL) is stirred and cooled to -70 C. under a nitrogen atmosphere. To this is added a 2.5M solution of n-butyl lithium in hexanes (3.52 mL) at -70 C. The mixture is stirred for 30 minutes then a solution of 3-chloro-4-methylpyridine (1.02 g) in dry tetrahydrofuran (10 mL) is added. The mixture is stirred for a further 40 minutes. A solution of 3-cyclopentyloxy-4,N-dimethoxy-N-methylbenzamide (2.23 g) in dry tetrahydrofuran (10 mL) is added and the mixture stirred at -70 C. for 30 minutes, -40 C. for 30 minutes, 0 C. for 30 minutes, and room temperature for 1 hour. A mixture of ethanol and hydrochloric acid 19:1 (40 mL) is added and then the reaction mixture is partitioned between brine (40 mL) and diethyl ether (40 mL). The ethereal phase is dried over sodium sulfate and concentrated in vacuo to give a pale yellow solid (3.0 g). The solid is triturated with diethyl ether and then purified by flash chromatography (ethyl acetate eluent on a silica column) to give a solid (1.6 g). The solid is triturated with diethyl ether, collected and dried to afford 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(3-chloropyrid-4-yl)ethanone (1.35 g) as a cream solid m.p. 124-125 C. ?Elemental analysis: C,66.2; H,5.89; N,4.12%; calculated for C19 H20 ClNO3: C,65.99; H,5.83;[N,4.05%.]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72093-04-0, 3-Chloro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Rhone-Poulenc Rorer Limited; US5935978; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem