Month: April 2022

Synthetic Route of 29681-44-5, Adding some certain compound to certain chemical reactions, such as: 29681-44-5, name is Methyl 5-bromonicotinate,molecular formula is C7H6BrNO2, 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 29681-44-5.

To a solution methyl 5-bromonicotinate (5 g, 23 mmol) in ethanol (40 mL) was added hydrazine hydrate (6 mL, 115 mmol). The reaction mixture was refluxed at 90 C for 4 h. After this time, the reaction mixture was evaporated to dryness and then redissolved in ethyl acetate. The organic layer was washed with water, dried and evaporated to yield 5 -bromonicotinohydrazide (3.4 g, 72 %). LCMS Method T: retention time 0.573 min; [M+l] = 216.0, 218.0.

According to the analysis of related databases, 29681-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JOHNSON, James A.; LLOYD, John; FINLAY, Heather; JIANG, Ji; NEELS, James; DHONDI, Naveen Kumar; GUNAGA, Prashantha; BANERJEE, Abhisek; ADISECHAN, Ashokkumar; WO2011/28741; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 929617-30-1, Adding some certain compound to certain chemical reactions, such as: 929617-30-1, name is 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine,molecular formula is C7H6BrN3, 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 929617-30-1.

To a solution of 5-Bromo-3-methyl-lH-pyrazolo[3,4-c]pyridine from Example 102 (106 mg, 0.5 mmol) in DMF (5 mL) was added Pd(dppf)Cl2 ( 20 mg ), saturated solution of Na2C03 ( 1 mL ) and lH-pyrazol-3-ylboronic acid ( 67 mg, 0.6 mmol ). The mixture was stirred under argon for 16 h at 80 C. After cooling down, the solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE = 1 : 1) to afford 103 (15 mg, 15% ). 1H NMR (500 MHz, MeOD) delta 8.96 (s, 1H), 8.23 (s, 1H), 7.71 (s, 1H), 6.90 (d, J= 1.5, 1H), 2.65 (s, 3H). ESI MS m/z = 200.1 (M+l)

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. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; LEE, Wendy; TSUI, Vickie Hsiao-Wei; WANG, Xiaojing; WEN, Zhaoyang; WO2013/24002; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 112110-07-3, 5-(Trifluoromethyl)pyridin-3-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, 112110-07-3, blongs to pyridine-derivatives compound. Formula: C6H5F3N2

A mixture of Pd2(dba)3 (11 mg, 0.012 mmol) and BrettPhos (13 mg, 0.025 mmol) in l,4-dioxane (1 mL) was stirred at 50 C for 10 min. l-(3-chloro-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (80 mg, 0.25 mmol), 5-(trifluoromethyl)pyridin-3-amine (49 mg, 0.30 mmol) in dioxane (5 mL) and CS2CO3 (248 mg, 0.762 mmol) were added and the resulting mixture was stirred at 100 C for 16 h. A black brown mixture was formed. LCMS (Rt = 0.702 min; MS Calcd: 440.2; MS Found: 440.9 [M+H]+). The reaction mixture was diluted with DCM (10 mL), filtered and concentrated. The residue was purified by prep-HPLC (0.05% NH32O as an additive) and lyophilized to give l-(5-methyl-3-((5- (trifluoromethyl)pyridin-3-yl)amino)-5H-chromeno[4,3-c]pyridin-8-yl)pynOlidin-2-one (25.0 mg, yield: 22%) as a white solid. (1164) NMR (400 MHz, DMSO-r/e) d 1.53 (3H, d, J= 6.8 Hz), 2.00-2.09 (2H, m), 2.52 (2H, overlap with DMSO), 3.83 (2H, t , J= 7.6 Hz), 5.29 (1H, q, J= 6.8 Hz), 6.77 (1H, s), 7.30 (1H, dd, J = 8.4, 2.0 Hz), 7.39 (1H, d, J= 2.0 Hz), 7.91 (1H, d, J= 8.4 Hz), 8.42 (1H, s), 8.74 (1H, s), 9.79 (1H, t, J = 2.0 Hz), 8.94 (1H, d, J= 2.4 Hz), 9.85 (1H, brs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,112110-07-3, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89282-03-1, 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 89282-03-1 as follows.

A reaction mixture containing 3-ethynyl-5-nitro-1 -trityl-1 H-indazole (215 mg, 0.5 mmol), 3-iodo-pyridin-4-ol (132 mg, 0.6 mmol), copper (I) iodide (4.5 mg, 0.025 mmol), PdCI2(PPh3)2 and triethylamine (120 mg, 1.2 mmol) in DMF (3 ml_) was heated at 100 C overnight under argon. After the completion of reaction (shown by TLC), ethyl acetate (50 mL)was added and the reaction mixture was added to water. The organic layer was collected, washed with water, brine and concentrated under vacuum. After purification using silica (7% methanol in dichloromethane), the desired product was obtained (210 mg, 0.4 mmol ) in 80% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89282-03-1, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2008/153858; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 188425-85-6, 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. 188425-85-6, name is 2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide. A new synthetic method of this compound is introduced below.

Add in a 100ml round bottom flask11-bromodecanoic acid 1 g (3.77 mmol),EDCI (0.72 g, 3.77 mmol) and HoBT (0.5 g, 3.77 mmol),Add 40 ml of dichloromethane to react for 15 min.Then, Boscalid {2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide} 1.24 g (3.6 mmol) was added. After 4 h of reaction, 1.5 g of 2-chloro-N-(4-chlorobiphenyl-2-yl)-N-(11-bromoundecyl)nicotinamide was obtained in a yield of 93%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,188425-85-6, its application will become more common.

Reference:
Patent; China Agricultural University; Tan Zhaohai; Wang Jiayao; Liu Xuelian; Tang Dachao; Xiao Yumei; Li Jiaqi; (46 pag.)CN109053801; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1149-24-2 , The common heterocyclic compound, 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, 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.

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

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. 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate, the common compound, a new synthetic route is introduced below. Formula: C8H8BrNO2

(2-Fluoro-4-methoxyphenyl)boronic acid (177 mg, 1.043 mmol), methyl 5-bromo-4- methylpyridine-2-carboxylate (200 mg, 0.869 mmol), 1,3 bis(di-tert-butylphosphino)ferrocene palladium dichloride (89 mg, 0.130 mmol), cesium carbonate (623 mg, 1.913 mmol) and THF (5 mL) were sealed in a microwave vessel and subject to microwave irradiation at 140 C for 20 min. The reaction crude was combined with the crude from an identical probe reaction (44.3 mg scale). Volatiles were removed under reduced pressure. The resulting pot residue was purified by preparative HPLC (reverse phase, Kromasil 100-5C18, 100×21.1 mm) eluting with acetonitrile/water + 0.1% TFA (30% to 100% organic in 10 min, then to 100% for 2 min, 20 mL/min). Related fractions were pooled and evaporated under reduced pressure to afford a dark solid. This solid was further purified by flash chromatography (Si02, Biotage SNAP Cartridge, silica gel, KP-Sil, 50 g cartridge). The column was eluted with an EtOAc hexanes mixture (0% to 100%). Related fractions were pooled and evaporated to afford a light yellow oil as the titled compound. LCMS calc. = 275.10; found = 276.11 (M+H)+.

The synthetic route of 886365-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LU, Zhijian; CHEN, Yi-Heng; SMITH, Cameron; LI, Hong; THOMPSON, Christopher, F.; SWEIS, Ramzi; SINCLAIR, Peter; KALLASHI, Florida; HUNT, Julianne; ADAMSON, Samantha, E.; DONG, Guizhen; ONDEYKA, Debra, L.; QIAN, Xiaoxia; SUN, Wanying; VACHAL, Petr; ZHAO, Kake; WO2012/58187; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1110782-41-6, 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. 1110782-41-6, name is 6-Chloro-5-(trifluoromethyl)nicotinic acid. A new synthetic method of this compound is introduced below.

To a stirred solution of the appropriate amine (0.72 mmol), EDC (1.14 mmol) and HOBT (0.76 mmol) in DCM (5 mL) were added DIPEA (1.52 mmol) and the relevant carboxylic acid (0.76 mmol). The reaction mixture was stirred at r.t. for 18 h, then quenched with water (10 mL). The organic layer was separated, dried (magnesium sulphate), concentrated in vacuo and purified using preparative HPLC, to yield the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1110782-41-6, 6-Chloro-5-(trifluoromethyl)nicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA S.A.; ALI, Mezher, Hussein; BROWN, Julien, Alistair; DE CANDOLE, Benjamin, Charles; HUTCHINSON, Brian, Woodside; LANGHAM, Barry, John; NEUSS, Judi, Charlotte; QUINCEY, Joanna, Rachel; TREVITT, Graham, Peter; WO2010/146351; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6945-67-1, 2-Bromo-4-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, Computed Properties of C5H3BrN2O2, blongs to pyridine-derivatives compound. Computed Properties of C5H3BrN2O2

Preparation 35 To a suspension of 2-bromo-4-nitropyridine (1.0 g) in ethanol (5 ml) was added a solution of sodium ethoxide in ethanol (20%, 2 ml), and the resultant mixture was stirred at 85 C. for 1.5 hours. After cooling, the mixture was diluted with dichloromethane and washed with water and brine. The separated organic layer was dried over sodium sulfate and evaporated under reduced pressure to give 2-bromo-4-ethoxypyridine (927 mg). 1H-NMR (CDCl3): delta1.43(3H,t,J=7.0 Hz), 4.08(2H,q,J=7.0 Hz), 6.76(1H,dd,J=5.8 Hz,2.3 Hz), 6.98(1H,d,J=2.3 Hz), 8.15(1H,d,J=5.8 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6945-67-1, 2-Bromo-4-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6521643; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide. This compound has unique chemical properties. The synthetic route is as follows. Formula: C10H13ClN2O

To a solution of N-(6-chloropyridin-2-yl)-2,2-dimethylpropanamide (10.6 g, 50 mmol) in THF (100 mL) n-butyllithium (2.5 M solution in hexane, 50 mL, 125 mmol) was added. The resulting mixture wasstirred at -20C for 3 h. After the addiction of DMF (4 mL) the reaction mixture was allowed to warm to room temperature and then was quenched with 0.5 M HCI. Ethyl acetate was added, the organic phase was washed with water, sat. K2003 and with brine. The crude material was purified by Si-column eluting with cy to cy/ethyl acetate 7:3 toobtain the title product (6.7 g, 27.8 mmol, 56% yield). LC-MS (M-H) =241.3

With the rapid development of chemical substances, we look forward to future research findings about 86847-84-9.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem