Category: pyridine-derivatives

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. 67938-76-5, name is (5-Chloropyridin-2-yl)methanamine, molecular formula is C6H7ClN2, 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: (5-Chloropyridin-2-yl)methanamine

To a mixture of A-l (2.00 g, 14.03 mmol) in THF (30 mL) was added TFAA (4.42 g, 21.05 mmol), then the mixture was stirred at 20 °C for 16 hours. The mixture was concentrated and the resulting residue was diluted with 0 (50 mL), and extracted with EtOAc (100 mL x 2). The combined organic phase was washed with sat. Na2C03 (30 mL), water (50 mL) and brine (50 mL), dried over Na2S04, filtered and concentrated to give A-2 (3.10 g, 12.99 mmol) as a solid. 1H NMR (400MHz, CDC13) = 8.54 (d, 1H), 7.85 – 7.60 (m, 2H), 7.25 (d, 1H), 4.63 (d, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 67938-76-5.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (141 pag.)WO2018/98491; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 142896-15-9, Methyl 2,6-dimethylisonicotinate, 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 C9H11NO2, blongs to pyridine-derivatives compound. Computed Properties of C9H11NO2

General procedure: Compound 100: 3-(2,6-Dimethyl-pyridin-4-yl)-3-oxo-propionitrile. Compound 100 was obtained according to general procedure VII(ii) starting from compound 99. Compound 100 was used in the next step without further purification. M/Z (M+H)+ = 175.2. Method (ii): Under anhydrous condition, to a solution of acetonitrile (2.0 equiv.) in THF (c=0.4 mol.L-1) cooled at -78C, BuLi (1.6N in hexane – 2 equiv.) was added dropwise. The reaction mixture turned light beige. The mixture was stirred for 1 hour at -78C, then the acid derivative (acid chloride or ester – 1.0 equiv.) was added dropwise. The reaction mixture was stirred at -78C for 1 hour, after which time it was allowed to warm to 0C and hydrolysed with AcOH. The reaction mixture was concentrated, dried under reduced pressure at 50C with P2O5 for 18 hours.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,142896-15-9, Methyl 2,6-dimethylisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Domain Therapeutics; Mayer, Stanislas; Schann, Stephan; EP2666775; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 891855-87-1, 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.891855-87-1, name is 4-Amino-2-ethylaminopyridine, molecular formula is C7H11N3, molecular weight is 137.18, as common compound, the synthetic route is as follows.

0.94 g of the compound described under INT12) is dissolved in 50 ml 1-propanol. 1.85 g of the compound described under INTT5) is added and it is stirred for 4 hours under reflux. After cooling, the reaction mixture is filtered. After purification by chromatography on silica gel, the solid substance yields 1.48 g of title compound as pH-dependent 5-(E/Z)-isomer mixture. 1 H-nMR (DMSO-d6, stored over K2CO3, main isomer): delta=1.13 (t, 3H); 1.26 (t, 3H); 3.24 (pentuplet, 2H); 4.25 (q, 2H); 4.72 (d, 1H); 5.28 (d, 1H); 5.39 (d, 1H); 5.90-6.07 (m, 1H); 6.25 (d, 1H); 6.44 (dd, 1H); 6.49 (t, 1H); 7.85 (d, 1H); 8.13 (s, 1H); 10.47 (s, 1H) ppm.

Statistics shows that 891855-87-1 is playing an increasingly important role. we look forward to future research findings about 4-Amino-2-ethylaminopyridine.

Reference:
Patent; Schulze, Volker Klaus; Eis, Knut; Wortmann, Lars; Kosemund, Dirk; Prien, Olaf; Siemeister, Gerhard; Hess-Stumpp, Holger; Eberspaecher, Uwe; Brittain, Dominic E.A.; Islam, Imadul; US2007/15759; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 59713-58-5, 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. 59713-58-5, name is Ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate, molecular formula is C10H8ClNO2S, 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.

REFERENCE EXAMPLE 11 4-Chlorothieno[2,3-b]pyridine-5-carboxylic acid A mixture of ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate (800 mg, 3.31 mmol) [Khan, M. A.; Guarconi, A. E., J. Heterocyclic Chem., 14, 807 (1977)] in 15 mL of ethanol and 5 mL of 2.5 N sodium hydroxide is heated at reflux for 90 minutes. The mixture is cooled to 0C and the pH is adjusted to 4 by the addition of 2 N hydrochloric acid. The mixture is stirred at room temperature and the resulting precipitate is collected by filtration and washed with water to provide 250 mg of 4-chlorothieno[2,3-b]pyridine-5-carboxylic acid as a white solid, mp 172-174 C.; 1H NMR (DMSO-d6) delta7.62 (d, J=6 Hz, 1H), 8.14 (d, J=6 Hz, 1H), 8.94 (s, 1H); MS 212.0 (M-H)-. Analysis for C8H4ClNO2S: Calcd: C, 44.98; H, 1.89; N, 6.56 Found: C, 44.99; H, 2.14; N, 6.43.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 59713-58-5, Ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate.

Reference:
Patent; Wyeth; US2004/242883; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1000025-07-9, 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 1000025-07-9, name is Vadadustat. This compound has unique chemical properties. The synthetic route is as follows.

Vadadustat (4.0g), L-Proline (2.85g) and acetone (60mL) were charged in a RBF at 25±5C and the contents were heated to 60-65C and stirred for 60 minutes at 60-65C. The reaction mass was slowly cooled to 25±5C and maintained under stirring at 25±5C for 16 hours. The product obtained was filtered, washed with acetone (8 mL) and dried under vacuum for 16 hours at 40C. The solid obtained was identified as 1 :2 co-crystal of Vadadustat L-Proline. Yield: 6.1 g

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1000025-07-9, Vadadustat.

Reference:
Patent; MYLAN LABORATORIES LIMITED; JETTI, Ramakoteswara Rao; PILLI, Narasimha Murty; PATHURI, Srinivasarao; GOLIVI, Ramamohana Rao; JAYACHANDRA, Sureshbabu; (36 pag.)WO2020/75199; (2020); A1;,
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 67367-24-2, name is Methyl 4-hydroxynicotinate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H7NO3

Reference example 30: methyl 5-bromo-4-hydroxypyridine-3-carboxylate To a suspension of methyl 4-hydroxypyridine-3-carboxylate (CASNo.67367-24-2) (1.96 g) in acetonitrile (20 mL)/acetic acid (4 mL) was added N-bromosuccinimide (CASNo.128-08-5) (2.39 g) at room temperature, and the mixture was stirred at 60 degrees C for 4 hours followed by concentration. To the obtained residue was added acetone, and the mixture was stirred for 5 min. The insoluble matter was collected by filtration to obtain the title compound having the following physical property values. Description: white powder; TLC: Rf 0.53 (ethyl acetate : methanol = 4 : 1);

With the rapid development of chemical substances, we look forward to future research findings about 67367-24-2.

Reference:
Patent; ONO Pharmaceutical Co., Ltd.; ISHIDA, Akiharu; MATSUSHITA, Takeshi; SEKIGUCHI, Tetsuya; KOMAGATA, Tatsuya; NISHIO, Takuya; EP2871179; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60186-13-2, 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 60186-13-2, name is 2,4,6-Trichloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1 (1.00 mmol) in DMF (3 mL) was added (PPh3)2PdCl2 (21 mg, 0.030 mmol) under an N2 atm and the reaction mixture was stirred for 5 min, before 2-furyl(tributyl)tin (0.32 mL, 1.0 mmol) was added. The resulting mixture was stirred for the time and at the temperature given in Table 1. H2O (40 mL) was added and the aqueous mixture extracted with EtOAc (2 × 30 mL). The combined organic phases were washed with brine (30 mL), dried (MgSO4) and evaporated in vacuo. The 1H NMR spectrum of the crude reaction mixture was recorded. The residue was dissolved in THF (8 mL), KF (ca. 200 mg) was added and the resulting suspension was stirred at ambient temperature for 18-20 h, evaporated with a small amount of silica gel and purified by flash chromatography on silica gel.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 60186-13-2, 2,4,6-Trichloro-3-nitropyridine.

Reference:
Article; Khoje, Abhijit Datta; Gundersen, Lise-Lotte; Tetrahedron Letters; vol. 52; 4; (2011); p. 523 – 525;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10273-89-9, Adding some certain compound to certain chemical reactions, such as: 10273-89-9, name is 2-(o-tolyl)pyridine,molecular formula is C12H11N, 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 10273-89-9.

EXAMPLE 1 Production of 2-[2-methyl-6-(2-methyl-propenyl)-phenyl]-pyridine A teflon (registered trade mark)-coated magnetic stirring rod was placed in a 4 mL pressure proof screw vial, dried with heating, then, N2 gas was allowed to flow through the reaction apparatus for several minutes to purge the whole reaction apparatus with nitrogen. The reaction vessel was left to cool to room temperature, then, under a nitrogen flow, into the reaction vessel was added Ru(cod)(cot) complex (0.1 mmol, 31.6 mg), trisfurylphosphine (0.1 mmol, 23.2 mg), 2-o-tolylpyridine (1 mmol, 169 mg), 2-methylpropenyl acetate (3 mmol, 342.4 mg) and toluene (1 mL), and the reaction vessel was sealed. The mixture was heated at 100 C. by an oil bath, and reacted for 24 hours. 50 hours after, the reaction solution was left to cool to room temperature, then, an internal standard was added, and the product was quantified by gas chromatography. Isolation of the product was carried out by silica gel column chromatography (i.d.=30 mm; length=170-250 mm; hexane:EtOAc:Et3N=8:1:0.1; 25 mL each). A subject substance 2-[2-methyl-6-(2-methyl-propenyl)-phenyl]-pyridine was obtained with a yield of 86%. IR (neat) 3058 m, 2969 m, 2856 m, 1654 w, 1587 s, 1563 m, 1459 s, 1421 m, 1376 m, 1280 w, 1182 w, 1147 w, 1091 w, 1064 w, 1025 w, 987 w, 892 m, 840 m, 775 m, 752 s, 649 m, 622 m, 472 s, 441 s, cm-1 1H NMR (CDCl3) d 1.658 (d, J=1.4 Hz, 3H, CH3), 1.719 (dt, J=1.4 Hz, 3H, CH3), 2.083 (s, 3H, CH3), 5.802 (s, 1H, CH), 7.11-7.28 (m, 5H, ArH), 7.700 (td, J=7.6 Hz, 1.9 Hz, 1H, ArH), 8.692 (dd, J=4.9 Hz, 1.9 Hz, 1H, ArH); 13C NMR (CDCl3) d 19.41, 20.21, 26.09, 121.42, 124.33, 125.18, 127.23, 127.37, 128.12, 134.93, 135.76, 135.91, 137.15, 139.81, 149.19, 159.64; MS m/z (% relative intensity) 223 (M+, 5), 209 (17), 208 (100), 90 (10), 51 (10) Elemental Analysis Anal. Calcd for C16H17N: C, 86.05; H, 7.67; N, 6.27%. Found: C, 85.93; H, 7.38; N, 6.38%

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. 10273-89-9, 2-(o-tolyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OSAKA UNIVERSITY; US2009/43096; (2009); 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, the common compound, a new synthetic route is introduced below. Product Details of 131747-62-1

To a solution of 13 (250 mg, 1.010 mmol) in toluene 10 mL was added 3-(trifluoromethyl) picolinaldehyde (177.0 mg, 1.010 mmol). PTSA (384.5 mg, 2.021 mmol) was added to the reaction mixture and stirred at 120 C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude compound (E)-6-methoxy-5-morpholino-2-((3-(trifluoromethyl)pyridin-2-yl)methylene)-2,3-dihydro-1H-inden-1-one 67. The compound 67 was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 34% ethyl acetate in hexane to afford yellow coloured solid.

The synthetic route of 131747-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; US2015/72980; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73455-13-7, 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. 73455-13-7, name is 4,5-Dichloropicolinic acid. A new synthetic method of this compound is introduced below.

A mixture of 4,5-dichloropicolinic acid (100 mg, 521 imol; CAN 73455-13-7), 1-cyclopropyl-2- (5-methyl-i ,2,4-oxadiazol-3-yl)propan-2-amine hydrochloride (136 mg, 625imol; CAN 1415900-39-8), 2-bromo-i-ethylpyridinium tetrafluoroborate (284 mg, 885imol) and N,N-diisopropyl ethyl amine (212 mg, 281 iL) in dioxane (0.8 mL) was stirredfor 14 h at 80 C, poured onto ice / brine (1 x 25mL) and extracted with EtOAc (2 x 25mL). The combined extracts were washed with ice water / brine (25 mL), dried overNa2SO4 and filtered. The filtrate was brought to dryness and the residue was purified by column chromatography (silica gel, 10 g, heptane / ethyl acetate) to obtain the title compound (120 mg, 65%) as colorless liquid, LC-MS: 355.2 [MH?i.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73455-13-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FREI, Beat; GOBBI, Luca; GRETHER, Uwe; RICKLIN, Fabienne; ROEVER, Stephan; ROGERS-EVANS, Mark; ROMBACH, Didier; (49 pag.)WO2018/234284; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem