Day: April 14, 2022

Application of 62135-58-4, Adding some certain compound to certain chemical reactions, such as: 62135-58-4, name is Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate,molecular formula is C9H9N3O2, 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 62135-58-4.

Step 2Ethyl 3-(F 1 ,2,4ltriazolo 11 ,5-alpyridin-2-yl)-3 -oxoyrotanoate To a mixture of ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (590 mg, 3.09 mmol) and ethyl acetate (1.81 mL, 18.5 mmol) in THF (6 mL) at -50 C was quickly added lithiumbis(trimethylsilyl)amide (1 M in toluene, 9.26 mL, 9.26 mmol). The mixture was stirred for 30 mm, and then quenched with acetic acid, washed with water, sodium bicarbonate, and brine. Purification by chromatography (silica, 50 – 100% ethyl acetate in hexanes) gave ethyl 3- ([1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-oxopropanoate (350 mg, 49 %) as a clear oil.

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. 62135-58-4, Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BHAGIRATH, Niala; DOMINIQUE, Romyr; KENNEDY-SMITH, Joshua; LUCAS, Matthew C.; PADILLA, Fernando; WO2014/64134; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75115-28-5, Adding some certain compound to certain chemical reactions, such as: 75115-28-5, name is N3-Benzylpyridine-3,4-diamine,molecular formula is C12H13N3, 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 75115-28-5.

General procedure: The vial containing the crude diaminopyridine was equipped with a magnetic stir bar and sealed with a teflon screw cap. Aldehyde (2 mol eqwith respect to the theoretical yield of the first reaction) and then nBuOH was added via syringe to give a diaminopyridine concentration of 0.3 M based on the theoretical yield of the first reaction. The reaction mixture was stirred at 110 C for 18-24 h with needle inserted in septum to expose reaction to air. The mixture was cooled to room temperature, diluted with ethyl acetate, and poured into aqueous saturated NaHCO3. The organic phase was separated and the aqueous phase was extracted twice more into ethyl acetate. The combined organic phases were driedover Na2SO4. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel, typically using EtOAc, 0 ->10% MeOH.

According to the analysis of related databases, 75115-28-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Chaomin; Chen, Lily; Steinhuebel, Dietrich; Goodman, Andrew; Tetrahedron Letters; vol. 57; 25; (2016); p. 2708 – 2712;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38923-08-9 , The common heterocyclic compound, 38923-08-9, name is Ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate, molecular formula is C10H9N3O4, 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 stirred solution of ethyl 6-nitroimidazo[l,2-a]pyridine-2-carboxylate (A34, 7.30 g, 31.73 mmol) in methanol(lOOmL) was added Pd/C(1.6 g, 15.86 mmol) under N2 atmosphere and the reaction mixture was stirred under H2 ballon pressure at room temperature for 4h. after completion of reaction mixture filtered through celite bed and washed with EtOAc. The filtrate was concentrated to dryness. The residue was washed with n-pentane dried to get compound ethyl 6-aminoimidazo[l,2-a]pyridine-2-carboxylate A35 as a green solid. Yield: 4.50 g(70%) LC-MS(ES) m/z : 205.99[M+H]+.

The synthetic route of 38923-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (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. 98121-41-6, name is 3-Amino-5,6-dichloropyridine, molecular formula is C5H4Cl2N2, 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. Safety of 3-Amino-5,6-dichloropyridine

5-Amino-2,3-dichloropyridine (0.80 g) in dichloromethane (10 ml) was added to boron trifluoride etherate (0.92 ml) at -15 C. under nitrogen. Dichloromethane (15 ml) was added followed by t-butylnitrite (0.71 ml) in dichloromethane (5 ml). After 15 minutes the mixture was allowed to warm to -5 C. over 20 minutes. Hexane was added and the resulting solid was filtered, air-dried and washed with ether and stored at approximately -20 C. overnight. The solid was then heated until gas evolution had ceased and the product kugelrohr distilled to give 2,3-dichloro-5-fluoropyridine (0.104 g).

With the rapid development of chemical substances, we look forward to future research findings about 98121-41-6.

Reference:
Patent; Zeneca Limited; US5922732; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-46-4, 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.886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.

Thionyl chloride (71 mul, 962 mumol) is added to a mixture of 5-chloro-3-methyl-pyridine-2-carboxylic acid (150 mg, 874 mumol), toluene (1 ml) and DMF (20 mul). The mixture is heated to 60 C. for 1 hour. The mixture is concentrated in vacuo and the crude product used directly without further purification.

The chemical industry reduces the impact on the environment during synthesis 886365-46-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; US2015/57286; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6635-86-5, 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. 6635-86-5, name is 2-Amino-4-methyl-3-nitropyridine, molecular formula is C6H7N3O2, 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.

Part A:; A reaction vessel was purged with inert gas. All steps were performed under inert gas protection. The vessel was then charged with 7.50 L of acetic acid at 20-25 C. Next, 1.00 kg of the compound of formula 1 was added to the vessel. A yellow suspension was formed. This was followed by the addition of 1.07 kg of sodium acetate. A very thick, yellow suspension was formed and the reaction was noted to be slightly exothermic. The temperature was raised to about 27 C. The mixture was then cooled to about 15-20 C. and a sample was taken for high pressure liquid chomatography (HPLC) monitoring. A solution of 1.15 kg of bromine (1.1 eq.) and 2.5 L of acetic acid was prepared. A 10/11 portion of the solution, i.e., 1.0 eq. at 15-20 C. was added to the vessel over about 10-15 minutes. The addition was slightly exothermic and some cooling was necessary (Tmax=20 C.). HPLC was used to monitor the reactions progress immediately after the addition and then at 60 min. Less than 10% of the starting material was observed. Then the remainder of the solution was added and the reaction mixture stirred until completion, approximately 30-60 additional minutes. After the reaction was complete 10.0 L of ice water was added, dropping the temperature to 11 C. and forming a suspension. The suspension was stirred for another 30-60 minutes and the product was filtered, then washed with 3×2.50 L of ice water. The product was dried at 40 C. to a constant LOD. The yield was 1.45 kg (96%), yellow crystals. mp. 132 C. IR (KBr, cm-1): 1633, 1581, 1538, 1512, 1458, 1377, 1344, 1321, 1244, 869, 779. 1H-NMR (CDCl3) (delta, ppm): 2.55 (s, 3H), 5.85 (bs, 2H), 8.25 (s, 1H): 13C-NMR (CDCl3) (delta, ppm): 20.81, 112.14, 144.49, 151.91, 153.78 (2C); MS; (M+1): 232; Elemental Analysis: calcd for C6H6BrN3O2: C, 31.05; H, 2.60; N, 18.11; Br, 34.43; found: C, 30.95; H, 2.42; N, 17.45; Br, 34.80.

According to the analysis of related databases, 6635-86-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293304; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 138402-36-5, 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. 138402-36-5, name is 3-(Aminomethyl)-5-chloropyridine, 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.

To a suspension of 2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-ol, 2HCl (23.5 mg, 0.05 mmol) and bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate (46.6 mg, 0.10 mmol) in 1,4-dioxane (1 ml) was added Et3N (0.14 ml, 1.0 mmol). The mixture was stirred at rt for 2 h and then (5-chloropyridin-3-yl)methanamine (14.26 mg, 0.10 mmol) was added. The mixture was stirred at 50 C for another overnight. The mixture was concentrated, dissolved in DMF (2 mL), filtered and submitted for purification by semi-preparative HPLC to give N-((5-chloropyridin-3-yl)methyl)-2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-amine, 2TFA (1 mg, 1.34 mumol, 2.7 % yield). 1H NMR (400 MHz, DMSO-d6) delta 12.01 (s, 1H), 10.07 (s, 1H), 8.58 (d, J = 1.8 Hz, 1H), 8.51 (d, J = 2.3 Hz, 1H), 8.25 – 8.09 (m, 1H), 7.94 (d, J = 2.3 Hz, 1H), 7.79 (s, 1H), 7.69 (s, 1H), 4.82 (d, J = 4.5 Hz, 2H), 3.81-3.85 (m, 6H), 2.79 (s, 6H), 2.65-2.51 (m, 6H), 2.41 (s, 3H), 2.24 (s, 3H). (including one salt NH). LC-MS (Method 2): tR = 3.47 min, m/z (M+H)+ = 521.

According to the analysis of related databases, 138402-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Shyh-Ming; Urban, Daniel J.; Yoshioka, Makoto; Strovel, Jeffrey W.; Fletcher, Steven; Wang, Amy Q.; Xu, Xin; Shah, Pranav; Hu, Xin; Hall, Matthew D.; Jadhav, Ajit; Maloney, David J.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3483 – 3488;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72141-44-7 ,Some common heterocyclic compound, 72141-44-7, molecular formula is C6H6ClNO, 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.

A solution of 4-amino-3-fluorophenol (0.20 g, 1.6 mmol) in 4 mL of anhydrous DMA was treated with potassium tert-butoxide (0.24 g, 1.9 mmol). The resultant dark-red solution was stirred at RT for 1 hour in a capped vial. 4-Chloro-2- methoxypyridine (0.26 g, 1.6 mmol) was added and the reaction mixture was heated overnight at 100 C. Water (50 mL) was added and the solution was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine, dried ( a2S04), concentrated in vacuo and purified by silica gel column chromatography to obtain 2-fluoro-4-(2-methoxypyridin-4-yloxy)benzenamine (0.20 g, 58% yield). FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-i/6) delta 8.02 (d, J = 6.0 Hz, 1H ), 6.95 (dd, J = 2.8, 12.0 Hz, 1H), 6.82 (dd, J = 8.4, 8.8 Hz, 1H), 6.73 (dd, J = 2.0, 8.4 Hz, 1H), 6.54 (dd, J = 2.4, 6.0 Hz, 1H), 6.10 (d, J = 2.4 Hz, 1H), 5.17 (s, 1H), 3.81 (s, 3H); MS (ESI) m/z: 235.0 (M+H +).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72141-44-7, its application will become more common.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel L.; PETILLO, Peter A.; KAUFMAN, Michael D.; WO2013/36232; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 83766-88-5, 2-(tert-Butoxy)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, Recommanded Product: 83766-88-5, blongs to pyridine-derivatives compound. Recommanded Product: 83766-88-5

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83766-88-5, 2-(tert-Butoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 21901-40-6, 4-Methyl-5-nitropyridin-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, name: 4-Methyl-5-nitropyridin-2-amine, blongs to pyridine-derivatives compound. name: 4-Methyl-5-nitropyridin-2-amine

mixture of 2-bromo-5-mtro-4-pyridine (100 mg, 0.461 raraol), copper (I) iodide (73.1 mg, 0.384 mmol) and methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (177 mg, 117 muL, 0.922 mmol) in dry DMF (1 mL) was heated under N2 at 120 0C overnight. The reaction mixture was cooled to room temperature and diluted with saturated NH4Cl (3.6 mL) and NH4OH (0.4 mL). The mixture was stirred until homogenous (a little water was added). The mixture was extracted with EtOAc (3 x 20 mL). The combined extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12 x 160 mm, 0-20% EtOAc in hexanes gradient) to afford 4- methyl-5-nitro-2-(trifluoromethyl)pyridine. LCMS calc. = 207.1; found = 207.1 (M+l)+. 1H NMR (500 MHz5 CDCl3): delta 9.17 (s, 1 H); 7.70 (s, 1 H); 2.72 (s, 3 H).

The synthetic route of 21901-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2007/81569; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem