Category: pyridine-derivatives

Synthetic Route of 164341-39-3, Adding some certain compound to certain chemical reactions, such as: 164341-39-3, name is (5-(Trifluoromethyl)pyridin-2-yl)methanamine,molecular formula is C7H7F3N2, 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 164341-39-3.

To a solution of triphosgene (0.07 g, 0.37 mol eq) in anh. CH2C12 (10 mL) was slowly added the amine If (0.2g, 1 mmol) solubilized in CH2C12 (10 mL) and DIEA (2.2 mol eq, 0.4 mL). After the addition was completed, the reaction mixture was stirred at room temp, for 15 min. Then the [5-(trifluoromethyl)-2- pyridyljmethanamine (1 mol eq, 0.18g) solubilized in CH2C12 (10 mL) and DIEA (2.2 mol eq, 0.4 mL) was added in one portion. The mixture obtained was stirred at room temp, for 12 h. The solvent was removed at reduced pressure, water was added and the mixture was extracted with EtOAc (3×20 mL). The recombined organic phases were anhydrified over sodium sulfate and evaporated to dryness. The residue was purified by crystallization from EtOAc to obtain the product as yellow solid (0.132g, 37% Yield). 1HNMR (DMSO, 400 MHz) delta 4.47 (d, 2H, J=6), 4.63 (s, 2H), 6.46 (dd, 1H, J=2), 6.80 (t, 1H, J=8), 7.57m, 2H), 7.72 (dd, 1H, J=2), 8.18 (dd, 1H, J=2), 8.22 (s, 1H), 8.90 (m, 1H), 10.66 (s, 1H). [M+1] 366.94 (C16H13F3N4O3 requires 366.29).

According to the analysis of related databases, 164341-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); 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.131803-48-0, name is Methyl 6-(bromomethyl)nicotinate, molecular formula is C8H8BrNO2, molecular weight is 230.06, as common compound, the synthetic route is as follows.category: pyridine-derivatives

NaH (60%, 48.5mg, 1.2lmmol) was added to a solution of (3) (200mg, 1.lSmmol) inDMF (7mL) at 5C under N2(g). The reaction mixture was stirred for 20mm thenmethyl 6-(bromomethyl)pyridine-3-carboxylate (345mg, 1 .Smmol) was added as asolution in DMF (3mL). The stirring was continued at 70C for lh. Reaction cooled toand poured onto water (lOOmL). Brine (25mL) was added and the aqueous wasextracted with EtOAc (2 x lOOmL). Combined organics were dried over Na25O4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography with CH2CI2/EtOAc (1:0-0:1) then EtOAc/MeOH (1:0-4:1) to give (4) (129mg, 35%).1H NMR (500 MHz, Chloroform-d), OH ppm: 9.04-9.13 (m, 1H), 8.70 (5, 2H), 8.19 (5,2H), 8.13 (dd, J=5.6, 2.3 Hz, 3H), 7.32 (d, J=8.2 Hz, 1H), 5.55 (5, 2H), 3.86 (5, 3H). LCMS (ES): Found 322.9 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131803-48-0, Methyl 6-(bromomethyl)nicotinate, and friends who are interested can also refer to it.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/181137; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, 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, Product Details of 571189-16-7, blongs to pyridine-derivatives compound. Product Details of 571189-16-7

Example 2: Preparation of 4-(6-Nitro-pyridin-3yl)-piperazine-1-carboxylic acid tert-butyl ester (2); 60.0 g of 20% Pd(OH)2/C, 1213.1 g (3.9 moles) of intermediate 2a, and isopropanol were charged and stirred in a Parr reactor, then purged under gas, followed by removal of the catalyst under pressure. The filtrates were concentrated in vacuo at -20 0C leaving 917 g of dry brown powder (crude yield -84%).

The synthetic route of 571189-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/32157; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 84249-14-9, name is 2-Amino-4-bromopyridine. A new synthetic method of this compound is introduced below., Product Details of 84249-14-9

Step 1 Preparation of 7-Bromo-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester To a stirred solution of 4-Bromo-pyridin-2-ylamine (4 g, 23.12 mmol) in toluene (40 mL) is added 3-Bromo-2-oxo-propionic acid ethyl ester (4.5 g, 23.12 mmol). The reaction mixture is heated at 115 C. for 16 hours. Reaction mixture is cooled to 0 C. then diluted with water and extract with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo to afford the title compound (6.5 g). 1H-NMR (400 MHz, DMSO-d6) delta: 1.31 (t, J=7.2 Hz, 3H), 4.26-4.33 (q, J=7.2 Hz, 2H), 7.18-7.20 (dd, J1=1.92 Hz, J2=7.16 Hz, 1H), 7.98 (s, 1H), 8.53 (d, J=7.32 Hz, 1H), 8.57 (s, 1H). LC-MS (m/z): [M+H]=271.0.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 84249-14-9, 2-Amino-4-bromopyridine.

Reference:
Patent; Curtis, Michael; Duclos, Brian A.; Ewin, Richard A.; Johnson, Paul D.; Johnson, Timothy Allen; Vairagoundar, Rajendran; Billen, Denis; Goodwin, Richard M.; Haber-Stuk, Andrea K.; Kyne, Graham M.; Sheehan, Susan M. K.; US2013/237502; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6443-85-2, Adding some certain compound to certain chemical reactions, such as: 6443-85-2, name is 2-(Pyridin-3-yl)acetonitrile,molecular formula is C7H6N2, 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 6443-85-2.

EXAMPLE 8 (Z)-3-(9-Ethyl-9H-carbazol-3-yl)-2-(pyridin-3-yl) acrylonitrile 9-Ethyl-9H-carbazol-3-yl-carboxaldehyde (4.46 g; 0.02 mol) and 3-pyridylacetonitrile (2.36 g; 0.02 mol) were dissolved in ethanol (25 mL). Sodium methoxide (1 mL of 25% methanol solution) was added. The mixture was then left standing at ambient temperature for 24 hours. The formed precipitate was collected by filtration and dried to give 2.4 g (37% yield) of the title compound as a yellow solid, m.p. 131-133 C. Anal. Calcd. for C22 H17 N3: C, 81.71; H, 5.30; N, 12.99. Found: C, 81.38; H. 5.49; N, 12.84. Mass spectrum (EI; M+) m/z 323. 1 H-NMR (DMSO-d6; 400 MHz) delta 8.98 (d, 1H), 8.75 (d, 1H), 8.60 (dd, 1H), 8.28 (s, 1H)1, 8.18 (dd, 1H), 8.12-8.16 (m, 2H), 7.8 (d, 1H), 7.68 (d, 1H), 7.51-7.56 (m, 2H), 7.29 (t, 1H), 4.49 (q, 2H), and 1.34 ppm (t, 3H).

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. 6443-85-2, 2-(Pyridin-3-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Home Products Corporation; US5710164; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6295-87-0 ,Some common heterocyclic compound, 6295-87-0, molecular formula is C5H7IN2, 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: A clean, washed boiling tube equipped with a magnetic stir bar was charged with 1-aminopyridinium iodide (1a) (0.0665 g, 0.3 mmol),(E)-chalcone (2a) (0.0520 g, 0.25 mmol) and NMP (1 mL). The mixture was stirred for 24 h at r.t. under O2 (balloon). After completion of the reaction, the mixture was poured into hypo solution (10 mL). The mixture was extracted with EtOAc (3 × 10 mL), dried over anhydrous Na2SO4 and the solvent removed under reduced pressure. The residue was purified through column chromatography using silica gel (20%EtOAc/hexane) to afford 3a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6295-87-0, its application will become more common.

Reference:
Article; Ravi, Chitrakar; Samanta, Supravat; Mohan, Darapaneni Chandra; Reddy, N. Naresh Kumar; Adimurthy, Subbarayappa; Synthesis; vol. 49; 11; (2017); p. 2513 – 2522;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89167-19-1, 3-Bromo-4-iodopyridine, 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, name: 3-Bromo-4-iodopyridine, blongs to pyridine-derivatives compound. name: 3-Bromo-4-iodopyridine

A mixture of 1-(oxan-2-yl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.94 g, 10.57 mmol), 3-bromo-4-iodopyridine (2.00 g, 7.05 mmol), potassium carbonate (2.92 g, 21.12 mmol) and Pd(dppf)Cl2.CH2Cl2 (580 mg, 0.710 mmol) in N,N-dimethylformamide (20 mL)/water (4 mL) was heated at 80 C. for 6 h under nitrogen. The resulting solution was extracted with ethyl acetate, and the combined extracts were dried over Na2SO4, filtered, and concentrated under vacuum. Purification by silica gel chromatography (7:3 ethyl acetate/petroleum ether) provided 3-bromo-4-[1-(oxan-2-yl)-1H-pyrazol-4-yl]pyridine (2.75 g) as a yellow oil. LCMS (ESI): [M+H]+=308.2.

The synthetic route of 89167-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 189449-41-0, (4-Chloropyridin-3-yl)methanol, 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, Product Details of 189449-41-0, blongs to pyridine-derivatives compound. Product Details of 189449-41-0

Example 21 3-chloromethyl-4-chloropyridine hydrochloride Thionyl chloride (0.714 mL, 9.78 mmol) was added at room temperature to dry DMF (7 mL). After 30 min the above solution was cannulated into the solution of 3-hydroxymethyl-4-chloropyridine (700 mg, 4.89 mmol) in DMF (3 mL). After 45 min, the product was precipitated by addition of dry ether (100 ml), washed with ether, and dried in vacuum to yield 813 mg (84percent) of the title compound. 1H NMR (CD3 OD) delta5.00 (s, 2H), 8.31 (d, 1H, J=5), 8.99 (d, 1H, J=5), 9.18 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189449-41-0, (4-Chloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Microcide Pharmaceuticals, Inc.; US6025352; (2000); A;; ; Patent; Microcide Pharmaceuticals, Inc.; US6057312; (2000); A;; ; Patent; Microcide Pharmaceuticals, Inc.; US6030965; (2000); A;,
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. 151509-03-4, name is Imidazo[1,5-a]pyridine-8-carbaldehyde, molecular formula is C8H6N2O, 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. Quality Control of Imidazo[1,5-a]pyridine-8-carbaldehyde

To a solution of imidazo[1,5-a]pyridine-8-carbaldehyde (60 mg, 0.41 mmol) in H20 (10 mL) was added 1-cyclohexylethan-1-one (52 mg, 0.41 mmol) and NaHCO3 (18 mg, 0.21 mmol),the reaction was warmed to reflux and stirred at for about 40 hours. Extracted with CH2C12 (3*10 mL), the combined organic phases were washed with sat. NaC1 (5 mL), dried overanhydrous Na2504, filtered, concentrated, the crude product was purified by Pre-TLC (DCM:MeOH = 15:1), got the product (10 mg, 9.6%) as a pale yellow solid. MS (ESI) m/e [M+1] 255.1.

With the rapid development of chemical substances, we look forward to future research findings about 151509-03-4.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; ZHANG, Guoliang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHOU, Changyou; (219 pag.)WO2016/161960; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1186647-69-7, 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A solution of 4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (103) (50 mg, 0.179 mmol) in DMF (1 mL) was cooled to 0 C, NaH (8.6 mg, 1.2 eq, 0.215 mmol) was added slowly and then 2-bromopropane was added dropwise. The solution was stirred overnight at room temperature. The mixture was concentrated in vacuo. The crude product was then purified by column chromatography using a gradient of CH2Cl2 in hexanes to afford 4-chloro-3-iodo-1-isopropyl-1H-pyrazolo[4,3-c]pyridine (301) (30 mg, 53% yield) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1186647-69-7, 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Intellikine, LLC; LIU, Yi; REN, Pingda; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; (58 pag.)EP2252293; (2018); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem