Month: April 2022

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

Electric Literature of 1132-37-2, 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.1132-37-2, name is Dipyridin-2-ylmethane, molecular formula is C11H10N2, molecular weight is 170.2105, as common compound, the synthetic route is as follows.

General procedure: In a dry flamed Schlenk tube under argon atmosphere, iridium dimers (1 eq.) and N^N ligands (2.2 eq.)were introduced in degassed 2:1 mixture of dichloromethane/methanol (8 mL). The reaction mixturewas stirred at 50 C for 6 h. After cooling down the solution to room temperature, excess of KPF6 (10eq.) was added affording a precipitate. The inorganic solid was filtered off and the filtrate wasevaporated. The solid was washed on a frit with diethyl ether (3×5 ml) and dried under vacuum to affordpure cationic iridium [Ir(C^N)2(N^N)][PF6] complexes.

The chemical industry reduces the impact on the environment during synthesis 1132-37-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Sauvageot, Elodie; Lafite, Pierre; Duverger, Eric; Marion, Ronan; Hamel, Matthieu; Gaillard, Sylvain; Renaud, Jean-Luc; Daniellou, Richard; Journal of Organometallic Chemistry; vol. 808; (2016); p. 122 – 127;,
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. 186203-81-6, name is tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate. A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate

Step a. To a solution of 2-bromo-5-phenylthiazole (CAS Number 133311-51-0; 0.158 g, 0.660 mmol) in toluene (5 ml) was added tert-butyl octahydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate (CAS Number 186203-81-6; 0.150 g, 0.660 mmol) at rt. Sodium tert-butoxide (0.120 g, 1.30 mmol) was added to the reaction mixture at rt. The resulting reaction mixture was degassed for 15 min and then treated with Pd2(dba)3 (0.030 g, 0.033 mmol) and Cy-JohnPhos (0.011 g, 0.033 mmol). The resulting reaction mixture was heated at 110C for 16 h then cooled to rt and poured into water (50 ml). The obtained mixture was extracted with EtOAc (3 x 20 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (2% MeOH in DCM) yielding tert-butyl l-(5-phenylthiazol-2-yl)octahydro-6H- pyrrolo[3,4-b]pyridine-6-carboxylate (0.163 g, 0.422 mmol). LCMS: Method C, 2.766 min, MS: ES+ 386.38.

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, 186203-81-6, tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (88 pag.)WO2018/60742; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84487-15-0, 2-Bromo-5-nitropyridin-4-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, 84487-15-0, blongs to pyridine-derivatives compound. SDS of cas: 84487-15-0

Step 2. Methyl 3- [ (4-amino-5-nitro-2-pyridinyl) oxy] benzoate Under nitrogen, to a solution of 2-bromo-5-nitro-4-pyridinamine (3.67g, 16.8 mmol) and methyl 3-hydroxybenzoate (2.82 g, 18.5 mmol) in DMF (100 mL), was added NaH (810 mg, 60% suspension, 20.2 mmol). 5 min later, the reaction mixture was heated to 65 C. The reaction mixture was concentrated, taken up in EtOAC, washed with NaOH solution (1. ON), saturated NH4C1 solution and brine, dried over Na2S04, filtered and concentrated to afford the title compound, which was used directly to next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84487-15-0, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/37197; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131674-40-3 ,Some common heterocyclic compound, 131674-40-3, molecular formula is C8H9NO2, 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 solution of l-(2-methoxypyridin-3-yl)ethanone (1 g, 6.62 mmol) in HBr/HOAc (30%, 20 mL) was added bromine (1.06 g, 6.62 mmol) at room temperature. The mixture was stirred at 60 C for 4 h. It was then cooled to room temperature and methyl tert-butyl ether (20 mL) was added to the mixture. A precipitate formed which was collected via vacuum filtration, collected and dried in vacuo to afford the title compound as a yellow solid. (1 g, 70 % yield).

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. 131674-40-3, 1-(2-Methoxypyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COOK, Andrew; COTE, Alexandre; DAKIN, Les, A.; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NASVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2014/151142; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89282-03-1, 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 89282-03-1, name is 3-Iodopyridin-4-ol. This compound has unique chemical properties. The synthetic route is as follows.

Step 2. 4-chloro-3-iodopyridine (47)[00371] A stirred solution under nitrogen of 46 (2.00 g, 9.05 mmol) in POCl3 (20 ml) was heated to reflux for four hours, then rt. The reaction mixture was poured slowly into ice and the pH was adjusted to 10-1 1 with an aqueous solution of ammonium hydroxide. The aqueous layer was extracted twice with dichloromethane.The combined organic layer was washed with brine, dried over anhydrous Na2SC^, filtered and concentrated to afford the title compound 47 (1.27 g, 5.30 mmol, 58%) as a brown solid. MS: 239.9 (M+l).

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 89282-03-1, 3-Iodopyridin-4-ol.

Reference:
Patent; METHYLGENE, INC.; RAEPPEL, Stephane; SAAVEDRA, Oscar; CLARIDGE, Stephen; VAISBURG, Arkadii; GAUDETTE, Frederic; ISAKOVIC, Ljubomir; DEZIEL, Robert; WO2008/46216; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129013-83-8, 3-(4-Bromophenyl)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: 129013-83-8, blongs to pyridine-derivatives compound. Recommanded Product: 129013-83-8

A mixture of the boronate from Step 1,3-(4-bromophenyl)pyridine from Step 2 (1.5 eq), [1,1′-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq) and 2M aqueous sodium carbonate (5 eq) in N,N-dimethylformamide (7 ml/mmol) was stirred at 85 C. for 1 hour. After cooling, the mixture was partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with a 7:3 mixture of ethyl acetate and methylene chloride to afford the N-Isopropyl-1-{3-[4-(pyridin-3-yl)phenyl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound as a solid. 1H NMR (CDCl3) delta 1.30 (d, 6H), 4.25 (m, 1H), 7.35 (m, 1H), 7.39-7.48 (m, 2H), 7.60-7.75 (m, 6H), 7.80 (d, 1H), 7.90 (d, 1H), 8.58 (d, 1H), 8.70 (m, 1H), 8.82 (d, 1H), 8.88 (s, 1H), 9.08 (s, 1H), 9.68 (br, NH).

The synthetic route of 129013-83-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Albaneze-Walker, Jennifer; Ceglia, Scott; Murry, Jerry Anthony; Soheili, Arash; US2004/102472; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem