Month: April 2022

Electric Literature of 153374-33-5, 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. 153374-33-5, name is 1-Methyl-1H-pyrrolo[3,2-b]pyridine, molecular formula is C8H8N2, 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.

General procedure: To a solution of 14a-d (2.5 mmol) in anhydrous dichloromethane (10 mL) anhydrous aluminum chloride (1.2 g, 8.8 mmol) was slowly added. The reaction mixture was stirred at room temperature (in the case of 15b) or heated under reflux for 10 min (in the case of 15a,c,d) and bromoacetyl bromide (0.2 mL, 2.5 mmol) in dichloromethane (2 mL) was added dropwise. The resulting solution was allowed to stir under reflux for 15-40 min. After cooling, water and ice were slowly added and the obtained precipitate was filtered off and purified by column chromatography using ethyl acetate (for compounds 15a, c) or dichloromethane/ethyl acetate (95/5) (for compound 15b,d) as eluent. For compounds 15b-d see supplementary material.

According to the analysis of related databases, 153374-33-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Carbone; Pennati; Barraja; Montalbano; Parrino; Spano; Lopergolo; Sbarra; Doldi; Zaffaroni; Cirrincione; Diana; Current Medicinal Chemistry; vol. 21; 14; (2014); p. 1654 – 1666;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 929617-30-1 ,Some common heterocyclic compound, 929617-30-1, molecular formula is C7H6BrN3, 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 500 mL round bottom flask containing 75 mL dry THF was dissolved 5- bromo-3-methyl-1 /-/-pyrazolo[3,4-c]pyridine (5.5 g, 25.9 mmol), and the contents were cooled to -15 0C. Sodium hydride (1.24 g (60% by wt., 31.1 mmol) was slowly added in portions to the cold stirring mixture, wherein vigorous gas evolution was observed (NOTE: Use caution during handling and addition of sodium hydride). After stirring for 15 min, benzenesulfonyl chloride (3.66 ml_, 28.5 mmol) was added dropwise via syringe. After stirring 15 min, the contents were removed from the cold bath and stirred with warming to room temperature over a 3 h period. The reaction mixture was poured onto a vigorously stirred solution of ice:water (1 :1 , 500 g), upon which the solid product crashes out. After stirring an additional 10 min, the heterogenous mixture was vacuum filtered and the filter cake was washed with additional water. The resultant solid was triturated with methanol (30 ml_), and the title compound is obtained as an off-white solid (10.75 g, 82%). 1H NMR: (CD3OD- d4) 9.27 (s, 1 H), 8.05 (s, 1 H), 8.01 (d, 2H), 7.69-7.73 (m, 1 H), 7.57-7.61 (m, 2H), 2.53 (s, 3H) ; LC/MS (MH+) = 351.8, 353.8; RT = 2.05 min.

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. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32651; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-62-1 ,Some common heterocyclic compound, 131747-62-1, molecular formula is C7H4F3NO, 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 175 (100 mg, 0.776 mmol) in toluene 15 ml was added 66 (203.9 mg, 1.16 mmol). PTSA (452 mg, 2.303 mmol) was added to the reaction mass 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 178, used in the 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,131747-62-1, its application will become more common.

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

Application of 851386-40-8, 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.851386-40-8, name is 4-Chloro-2,5-difluoropyridine, molecular formula is C5H2ClF2N, molecular weight is 149.53, as common compound, the synthetic route is as follows.

To a dry microwave vial under nitrogen was added (S)-isopropyl 2-(fert- butoxy)-2-(4-(4,4-dimethylpiperidin-l-yl)-2,6-dimemyl-5-(l,2,3,4-tetrahydroisoquinolin- 6-yl)pyridin-3-yl)acetate (46.8 mg, 0.090 mmol), 4-chloro-2,5-difluoropyridine (149.5 mg, 1.0 mmol), and acetonitrile (0.9 mL). The reaction was flushed briefly with nitrogen, treated with Hunig ‘s base (230 mu, 1.37 mmol), capped and heated in a microwave reactor at 85 – 95 C for 17h, followed by heating at 80 C for 36h in a sand bath. The crude reaction was purified via reverse phase Prep-HPLC to afford isopropyl (S)-2-(fert- butoxy)-2-(5-(2-(2,5-difluoropyridin-4-yl)-l,2,3,4-tetrahydroisoquinolin-6-yl)-4-(4,4- dimethylpiperidin-l-yl)-2,6-dimethylpyridin-3-yl)acetate, 42 mg (quant). LCMS (M+l) = 635.4.

The chemical industry reduces the impact on the environment during synthesis 851386-40-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (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. 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