Day: April 18, 2022

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. 52311-50-9, name is 2-Chloro-4-ethoxypyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

N-(4-ethoxypyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide To a degassed mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (9.4 g, 38 mmol) and 2-chloro-4-ethoxypyridine (5 g, 31.7 mmol) in dioxane was added Brettphos-prePd (catalytic amount) and Cs2CO3 (12.3 g, 37.8 mmol) under N2 atmosphere. The mixture was heated to 100 C. and stirred for 3.5 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was purified on silica-gel (PE: EA=100%?30%) to give N-(4-ethoxypyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (8.8 g, yield 75%). 1HNMR (400 MHz, CDCl3): delta=8.74 (s, 1H), 8.05?8.02 (m, 1H), 8.01 (s, 1H), 7.94?7.89 (m, 4H), 6.60?6.59 (m, 1H), 4.20?4.14 (m, 2H), 1.47-1.43 (m, 3H), 1.36 (s, 12H), MS (ESI): M/Z (M+1)=369.19.

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, 52311-50-9, 2-Chloro-4-ethoxypyridine.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1279815-46-1, 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.1279815-46-1, name is 1-(2-Bromopyridin-4-yl)cyclopropanecarbonitrile, molecular formula is C9H7BrN2, molecular weight is 223.0693, as common compound, the synthetic route is as follows.

To a solution of l-(2-bromo-pyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.20 mmol) in toluene (30 mL) is added DIBAL-H (10.4 mL, 1M in toluene) at -78C. The mixture is stirred 1 hour at -78C and warmed to room temperature. After 1 hour, ethyl acetate (30 mL) is added, followed by 1M aqueous solution of H2S04 (30 mL). Phases are separated and the aqueous layer is extracted with ethyl acetate (3 x 50 mL). The combined organic layers are dried over MgS04, filtered and concentrated to afford crude l-(2-bromo-pyridin-4-yl)-cyclopropanecarbaldehyde (ES+ m/z 226.48; 228.47), which is used without purification.

The chemical industry reduces the impact on the environment during synthesis 1279815-46-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; MAO, Can; RAZAVI, Hossein; WO2011/49917; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 28733-43-9, Adding some certain compound to certain chemical reactions, such as: 28733-43-9, name is 5-Bromonicotinamide,molecular formula is C6H5BrN2O, 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 28733-43-9.

To a solution of NaOH (22.9 g, 572 mmol) in water (245 mL) at 0-5 C. (ice salt bath) was added bromine (9.44 mL, 184 mmol) maintaining the temperature at 0-5 C., to produce a sodium hypobromite solution. To this NaOBr-sol. was added commercially available 3-bromonicotinamide (30.15 g, 150 mmol) all at once with vigorous stirring. After being stirred for 15 min, the solution is clear and mixture was heated to 70-75 C. for 45 min. Cooled to 23 C., saturated with solid NaCl, extracted with TBME/THF (3×300 mL), dried over Na2SO4. Removal of the solvent in vacuum gave a dark brown oil which was purified by silica gel column chromatography with heptane/EtOAc 1:1?2:3 to give the title compound as a brown solid (16.036 g, 62%). MS (ISP) 173.1 [(M+H)+], 175.2 [(M+2+H)+].

According to the analysis of related databases, 28733-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Palmer, Wylie Solang; Wichmann, Juergen; Woltering, Thomas Johannes; US2006/217387; (2006); 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.1122-72-1, name is 6-Methyl-2-pyridinecarboxaldehyde, molecular formula is C7H7NO, molecular weight is 121.14, as common compound, the synthetic route is as follows.SDS of cas: 1122-72-1

(i) 6-Methyl-2-hydroxymethylpyridine 6-Methylpyridine-2-carboxaldehyde (0.44 mmole) in 50 ml methanol was reduced with 20.6 mmole sodium borohydride at 0-5 C. After reduction was complete, the mixture was neutralized (pH 7.5) with 2N sulfuric acid, filtered, the filtrate concentrated band partitioned between chloroform and water. Evaporation of solvent from the organic layer gave 3.32 g of red-black oil which was used in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1122-72-1, 6-Methyl-2-pyridinecarboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; EP150984; (1991); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 183208-34-6 ,Some common heterocyclic compound, 183208-34-6, molecular formula is C7H5BrN2O, 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.

Example 44A tert-butyl (1S,2Z)-2-(5-bromo-2-oxo-1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)-1-(1H-indol-3-ylmethyl)ethylcarbamate A mixture of 5-bromo-7-aza-oxindole (D. Mazeas, et al., Heterocycles 1999, 50, 1065.) (213 mg, 1.0 mmol), L-BOC-tryptophanal (290 mg, 1.0 mmol) and piperidine (40 muL) in ethanol was refluxed for 2.5 hours and concentrated. The residue was triturated with dichloromethane (1 mL) and hexane (6 mL) and dried to provide the desired product (512 mg). MS (DCI/NH3) m/e 483, 485 (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,183208-34-6, its application will become more common.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 96428-50-1 , The common heterocyclic compound, 96428-50-1, name is Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, molecular formula is C18H18N2O3, 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.

Example 24A Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate 31.45 g (101.3 mmol) of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate from Example 23A were dissolved in 2 l of ethyl acetate, 3.15 g of 10% Pd/carbon were added and the mixture was stirred at RT and standard hydrogen pressure for 5 h. The mixture was filtered through kieselguhr, the filter cake was washed well with ethyl acetate/methanol and the filtrate was concentrated to dryness. This gave 21.94 g of the target compound (98% of theory, purity 99%). LC-MS (Method 1): Rt=0.61 min MS (ESpos): m/z=221 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): delta=1.36 (t, 3H), 2.60 (s, 3H), 4.36 (q, 2H), 6.78 (d, 1H), 6.98 (t, 1H), 8.73 (d, 1H), 10.60 (br s, 1H).

The synthetic route of 96428-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; VALOT, Gaelle; LINDNER, Niels; FOLLMANN, Markus; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; REDLICH, Gorden; DIETZ, Lisa; Ll, Volkhart Min-Jian; (94 pag.)US2017/57954; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, 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, 59290-81-2, blongs to pyridine-derivatives compound. Safety of 2-Methyl-5-nitro-3-pyridinecarboxylic acid

Step 1: Synthesis ofZ-1aED-1 a (15.6 g, 85.7 mmol) is placed in ie/f.-BuOH (300 mL), combined with DPPA (27 mL, 125 mmol) and NMM (12 mL, 108 mmol) and refluxed for 5 h. After cooling, saturated sodium chloride solution is added and the mixture is extracted several times with EA. The combined organic phases are washed with saturated sodium chloride solution, dried on MgS04, filtered and evaporated down using the rotary evaporator. The residue is taken up in water and freeze-dried. The resulting Z-1 a (HPLC-MS: tRet. = 1 .73 min; MS (M+H)+ = 254) is used 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,59290-81-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ETTMAYER, Peter; STEURER, Steffen; WO2011/117382; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 135124-71-9 ,Some common heterocyclic compound, 135124-71-9, molecular formula is C7H6N2O, 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.

d) 5-Cyano-pyridine-3-carbaldehyde A black suspension of (5-cyano-pyridin-3-yl)-methanol (0.070 g, 0.52 mmol), anhydrous CH2Cl2 (1.04 mL) and manganese oxide (0.181 g, 2.09 mmol) was heated to reflux and monitored by TLC. After 8 h, the reaction mixture was cooled to room temperature and additional manganese oxide (0.095 g, 1.1 mmol) was added to the reaction flask. The reaction mixture was then heated to reflux. After 18 h, the reaction was still not complete by TLC and additional manganese oxide (0.097 g, 1.1 mmol) was added to the reaction flask. After heating at 60 C. for 72 h, the reaction mixture was cooled to room temperature, diluted with EtOAc (50 mL), passed through celite and washed with additional EtOAc (50 mL). The organic filtrate was dried over MgSO4, filtered through sintered glass and concentrated to yield 0.064 g (93%) of a white solid. It was purified by column chromatography (elution with EtOAC:hexanes, 1:3) and yielded 0.038 g (55%) of the title compound as a white solid. 1H NMR (CDCl3): 10.17 (s, 1H), 9.28 (d, J=1.9 Hz, 1H), 9.11 (d, J=2.2 Hz, 1H), 8.45 (dd, J=2.2, 1.9 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135124-71-9, its application will become more common.

Reference:
Patent; Cytovia, Inc.; US2006/104998; (2006); 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. 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, the common compound, a new synthetic route is introduced below. Formula: C6H5BrClN

Example 1; Synthesis of 3-(2-amino-6-quinazolinyl)-1 -(3-chlorophenyl)-4-methyl-2(1 H)- pyridinone; Step 1 : 2-(4-methoxybenzyloxy)-3-bromo-4-methyl; Pyridine To a mixture of 60% NaH in mineral oil (0.290 g, 7.27 mmol) in THF (15 ml_) at RT in a resealable pressure vessel was added (4-methoxyphenyl)methanol (0.906 ml, 7.27 mmol). After 5 minutes, 3-bromo-2-chloro-4-picoline (1.00 g, 4.84 mmol) was added and the mixture was heated to 75 0C. After 1 hr, water was added and the mixture was diluted with EtOAc. After washing with water and brine, the organic fraction was dried with sodium sulfate and purified by silica gel chromatography using 0-30% EtOAalphahexanes to afford 2-(4-methoxybenzyloxy)- 3-bromo-4-methylpyridine as a colorless oil. M+H+ = 308.0.

The synthetic route of 55404-31-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2008/11109; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 189230-41-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 189230-41-9 as follows.

[0355] Reference AD [0356] Synthesis of 5-chloro-N-cyclopropyl-3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-l- yl)pyrido[3,4-b]pyrazin-2-amine [0358] [0359] Step 1 : 5-bromopyrido[3,4-b]pyrazine-2,3(lH,4H)-dione [0360] A solution of l,2-di(lH-imidazol-l-yl)ethane-l,2-dione (1.456 g, 7.66 mmol) and 2- bromopyridine-3,4-diamine (1.2 g, 6.38 mmol) in DMF (21.27 ml) was stirred at RT overnight. The precipitate was filtered and washed with anhydrous THF to give the title compound as a grey solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference:
Patent; ENVOY THERAPEUTICS, INC.; HITCHCOCK, Stephen; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; KIKUCHI, Shota; MACKLIN, Todd; HOPKINS, Maria; WO2014/28479; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem