Tag: M.W:100-200

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.1211523-71-5, name is 2-(2-Bromopyridin-3-yl)acetonitrile, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.SDS of cas: 1211523-71-5

To a 0C solution of 2-(2-bromopyridin-3-yl)acetonitrile (2.21 g, 11.21 mmol) inDMF (20 mL) was added NaH (60% dispersion in mineral oil, 1.12 g, 28.03 mmol) in portions. The resulting mixture was warmed to 60 C and stirred for 1.5 h. Tert-butylbis(2-chloroethyl)carbamate (3.26 g, 13.46 mmol) was added to the mixture and stirred for 2 h at 60 C. After cooling to RT, the reaction mixture was quenched with brine (50 mL), extracted with EA (3 x 100 mL). The combined organic layers were washed with brine (3 x 80 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica chromatography (eluting with EA: Hex = 1: 3, v/v) to give tert-butyl4-(2-bromopyridin-3-yl)-4-cyanopiperidine-1-carboxylate (1.56 g). MS: m/z 366 (M+H) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211523-71-5, 2-(2-Bromopyridin-3-yl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; JACOBIO-ALPHA PHARMACEUTICALS CO., LTD.; MA, Cunbo; GAO, Panliang; HU, Shaojing; XU, Zilong; HAN, Huifeng; WU, Xinping; KANG, Di; LONG, Wei; (202 pag.)WO2018/172984; (2018); A1;,
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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine. A new synthetic method of this compound is introduced below., Safety of 2-Chloro-4-hydrazinopyridine

A solution of (2-chloro-pyridin-4-yl)-hydrazine (1.0 g, 6.965 mmol), ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate, INT1 (1.67 g, 6.965 mmol) and triethylamine (1.92 mL, 13.758 mmol) in ethanol (25 mL) was stirred overnight at 80 C. The reaction mixture was concentrated under reduced pressure and residue purified by chromatography over silica gel (gradient of EA in heptane from 0 to 25%) to afford the title compound as a clear oil (765 mg, 34%). 1H NMR (300 MHz, chloroform-d) delta 1.39 (t, J=7.2 Hz, 3H), 4.39 (q, J=7.2 Hz, 2H), 7.26 (s, OH), 7.36 (d, J=5.5 Hz, 1H), 7.51 (d, J=1.9 Hz, 1H), 8.16 (s, 1H), 8.57 (d, J=5.4 Hz, 1H). MS m/z 320 (MH+).

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, 700811-29-6, 2-Chloro-4-hydrazinopyridine.

Reference:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6200-59-5, 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. 6200-59-5, name is Imidazo[1,2-a]pyridine-3-carbonitrile, molecular formula is C8H5N3, 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.

A solution of sodium methoxide (prepared from sodium (0.13 g, 5.65 mmol) and methanol (10 mL)) was added dropwise to a suspension of imidazo[1 ,2-a]pyridine-3- carbonitrile (4.0 g, 27.94 mmol) in methanol (15 mL) and the resulting mixture was stirred at ambient temperature overnight. Ammonium chloride (1 .64 g, 30.7 mmol) was then added and the mixture was heated at 90 C for 4h. The solvent was removed under reduced pressure and the resulting solid was treated with diethyl ether, filtered and purified by flash chromatography (dichloromethane/ ethanol) to give the title compound (4.47 g, 99%) as a white solid. LRMS (m/z): 161 (M+1 )+ 1H NMR delta (300 MHz, DMSO-d6): 7.21 (t, 1 H), 7.56 (t, 1 H), 7.79 (d, 1 H), 8.26 (s, 1 H), 8.67 (d, 1 H) .

According to the analysis of related databases, 6200-59-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); 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 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C12H9N3

CdSO4·3/8 H2O (0.026 g, 0.1 mmol), 3PBI (0.0195 g, 0.1 mmol), NaOH (0.0072 g,0.18 mmol), adipic acid (0.0146 g, 0.1 mmol), and water (6 mL) were added to a 15-mLTeflon reactor and heated under autogenous pressure at 160 C for 3 days. The reaction mixture was cooled to room temperature at a rate of 5 C h-1. Yellow pellet crystals of 3suitable for X-ray diffraction analysis were obtained (0.0123 g, yield: 27% based onCdSO4). Elemental analysis Calcd (%) for C18H15Cd N3O5 (465.73): C, 46.38; H, 3.22; N,9.02; found: C, 46.19; H, 3.24; N, 9.05. IR (KBr, cm-1): 2943(w), 1557(s), 1419(s), 1329(m), 1278(m), 1197(m), 1130(w), 1049(m), 962(m), 930(m), 816(m), 740(s), 700(m), 637(m), 519(w), 428(m).

With the rapid development of chemical substances, we look forward to future research findings about 1137-67-3.

Reference:
Article; Wang, Cui-Cui; Wang, Jin-Hua; Tang, Gui-Mei; Wang, Yong-Tao; Cui, Yue-Zhi; Ng, Seik Weng; Journal of Coordination Chemistry; vol. 68; 21; (2015); p. 3918 – 3931;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 956010-87-0, Adding some certain compound to certain chemical reactions, such as: 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine,molecular formula is C7H4F3N3, 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 956010-87-0.

Trifluoroacetic anhydride (2.6 mL, 18.7 mmol) was added to a solution of tetrabutylammonium nitrate (5.7 g, 18.7 mmol) in dichloromethane (50 mL) cooled to 00C in an ice bath. After 5 minutes, 3-(trifluoromethyl)-lH-pyrazolo[3,4-b]pyridine (0.5 g, 2.67 mmol) was added portionwise. The resulting solution was stirred at room temperature overnight. The reaction mixture was treated with saturated aqueous sodium bicarbonate, and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated to an oil. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (2:1) to give 5-nitro-3-(trifIuoromethyl)-lH-pyrazolo[3,4- b]pyridine (0.19 g, 31%) as a solid.

According to the analysis of related databases, 956010-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRADL, Stefan; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25968; (2011); A1;,
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

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

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

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

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