Category: 118289-17-1

Electric Literature of 118289-17-1 ,Some common heterocyclic compound, 118289-17-1, molecular formula is C6H4BrNO, 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.

General procedure: For the synthesis of 3a and 3b, methods ofEmmereich et al. [1] were adapted as follows: Phenylboronic acid, 2-bromopyridine-4/5-carboxyaldehydeand sodium carbonate (2M) were dissolved in a 1:1 mixture of toluene andethanol (v/v, 10ml). The mixture was degassed for 10 minutes and thendichlorobis(triphenylphosphine)palladium(II) was added. The reaction mixturewas heated at 80 C for 5 h under argon atmosphere. The mixture was allowed tocool to room temperature and then organic molecules were extracted intodichloromethane (3×20 ml). Combined extracts were dried over sodium sulphateand then filtered. Upon concentration under reduced pressure crude product wasobtained as dark yellowish green liquid. Chromatography over silica-gel gavethe title compounds (3a and 3b) as liquid or solid. 2-pheny-4-formylpyridine (3a): A mixture of phenylboronic acid (197 mg, 1.6 mmol),2-bromopyridine-4-carboxyaldehyde 2a(200 mg, 1.1 mmol), sodium carbonate (2M, 0.5 ml) and dichlorobis(triphenylphosphine)palladium(II)(37.7 mg, 5%) gave 3a (152 mg,77%) as clear oil. Rf (Etil Asetat:Hekzan, 1:6 v/v) = 0.3. 1H NMR (600 MHz, CDCI3)delta(ppm): 10.14(s, 1H), 8.94 (d, J = 6 Hz, 1H), 8.13 (s, 1H), 8.06 (dd, J = 12Hz and 6 Hz, 2H) , 7.63 (d, J = 6 Hz, 1H), 7.53-7.43 (m,3H). 13C NMR (150 MHz, CDCI3) delta (ppm): 191.6, 159.1,151.1, 142.5, 138.2, 129.7, 128.9, 127.0, 120.5, 118,9.

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. 118289-17-1, 2-Bromopyridine-4-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Alt?noelcek, Nuray; Aydemir, Murat; Tavasl?, Mustafa; Dos Santos, Paloma L.; Monkman, Andrew P.; Journal of Organometallic Chemistry; vol. 851; (2017); p. 184 – 188;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 118289-17-1, 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. 118289-17-1, name is 2-Bromopyridine-4-carboxaldehyde. A new synthetic method of this compound is introduced below.

To a chilled (-780C) solution of 2-bromo-pyridine-4-carbaldehyde (10.0 g, 53.8 mmol) in THF (100 mL) was added a 3 M solution of methylmagnesium chloride in THF (18 mL, 54 mmol) over a 10 minute period. After 1 hour, the yellow solution was allowed to warm gradually to room temperature over a 3 hour period. The reaction was quenched by the slow addition of saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (2 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to afford a brown oil. The crude material was purified by silica gel chromatography eluting with a gradient of 10-45% EtOAc in hexanes to afford l-(2- bromo-pyridin-4-yl)-ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,118289-17-1, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; DISALVO, Darren; FANDRICK, Daniel Robert; HARCKEN, Christian; KUZMICH, Daniel; LEE, Thomas Wai-Ho; LIU, Pingrong; LORD, John; MAO, Can; NEU, Jochen; RAUDENBUSH, Brian Christopher; RAZAVI, Hossein; REEVES, Jonathan Timothy; SONG, Jinhua, J.; SWINAMER, Alan, David; TAN, Zhulin; WO2010/36632; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 118289-17-1, 2-Bromopyridine-4-carboxaldehyde, 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, COA of Formula: C6H4BrNO, blongs to pyridine-derivatives compound. COA of Formula: C6H4BrNO

(a) 2-bromo-4-(difluoromethyl)pyridine To a solution of 2-bromoisonicotinaldehyde (2 g, 10.752 mmol) in dichloromethane was added DAST (6.613 g, 32.257 mmol) at -78 C. The mixture was warmed to room temperature slowly in 2 hours. The reaction mixture was quenched with saturated sodium bicarbonate and extracted with dichloromethane. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to give 2-bromo-4-(difluoromethyl)pyridine (2 g, yield 90%). 1HNMR (400 MHz, CDCl3): delta=8.52?8.51 (d, J=8.0 Hz, 1H), 7.63 (s, 1H), 7.40?7.38 (d, J=8.0 Hz, 1H), MS (ESI): M/Z (M+1)=207.95.

The synthetic route of 118289-17-1 has been constantly updated, and we look forward to future research findings.

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

Related Products of 118289-17-1 ,Some common heterocyclic compound, 118289-17-1, molecular formula is C6H4BrNO, 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.

General procedure: To a 50 mL two-necked flask equipped with magnetic stirrer and condenser was added 2-bromopyridine (1.0 eq), Pd(PPh3)4 (5 mol%), K2CO3 solution (2.0 eq) and toluene under N2 at room temperture. After reacted for 15 min, a solution of the boronic acid (1.2 eq) in EtOH was then added. The reaction mixture was then heated to 95 C and reacted for 4 h. After cooling to room temperature, to the reaction mixture aqueous NH4Cl was added and extracted three times with EtOAc. The organic extracts were then combined, washed with brine, dried with MgSO4 and then concentrated under reduced pressure. The crude product was then purified by silica gel column chromatography(Petroleum ether/EtOAc) to give compounds 1 and 5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,118289-17-1, its application will become more common.

Reference:
Article; Duan, Yingchao; Qin, Wenping; Suo, Fengzhi; Zhai, Xiaoyu; Guan, Yuanyuan; Wang, Xiaojuan; Zheng, Yichao; Liu, Hongmin; Bioorganic and Medicinal Chemistry; vol. 26; 23-24; (2018); p. 6000 – 6014;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 118289-17-1, 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. 118289-17-1, name is 2-Bromopyridine-4-carboxaldehyde, molecular formula is C6H4BrNO, 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.

Example 102 (method 2) (Synthetic Intermediate)(2-Bromo-pyridin-4-yl)-[5-(4-dimethylamino-piperidin-1-yl)-1-(2-trimethylsilanyl- ethoxymethyl)-1 H-benzoimidazol-2-yl]-methanone (as a mixture with the 6- regioisomer). Starting with Example 25, Step 1 was performed by following procedures describe for Example 42. Step 2 and Step 3 were performed by following procedures describe for Example 48.

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 118289-17-1, 2-Bromopyridine-4-carboxaldehyde.

Reference:
Patent; NOVARTIS AG; ASTEX THERAPEUTICS LIMITED; HOWARD, Steven; MORTENSON, Paul Neil; HISCOCK, Steven Douglas; WOOLFORD, Alison Jo-Anne; WOODHEAD, Andrew James; CHESSARI, Gianni; O’REILLY, Marc; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; CHO, Young Shin; YANG, Fan; CHEN, Christine Hiu-Tung; BRAIN, Christopher Thomas; LAGU, Bharat; WANG, Yaping; KIM, Sunkyu; GRIALDES, John; LUZZIO, Michael Joseph; PEREZ, Lawrence Blas; WO2010/125402; (2010); 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. 118289-17-1, name is 2-Bromopyridine-4-carboxaldehyde. A new synthetic method of this compound is introduced below., Computed Properties of C6H4BrNO

To a stirred suspension of (R)-2-methylpropane-2-sulfinamide (13.03 g, 108 mmol) and CS2CO3 (52.5 g, 161 mmol) in DCM (400 ml) was added 2-bromopyridine-4- carbaldehyde (20 g, 108 mmol) over 10 min. The reaction mixture was then stirred for 18.5 h at rt. The reaction mixture was concentrated and the residue was diluted with EtOAc (50 ml) and washed with brine (3 x 20 ml). The organic layer was dried over MgS04 and filtered and then the filtrate was concentrated. The residue was purified by normal phase chromatography using hexanes and EtOAc as eluents to afford (27.2 g, 87%) of (R)-N-[(lE)-(2-bromopyridin-4-yl)methylidene]-2-methylpropane-2-sulfinamide as a white solid. MS(ESI) m/z: 289-291.0 (M+H)+.

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, 118289-17-1, 2-Bromopyridine-4-carboxaldehyde.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DILGER, Andrew, K.; CORTE, James, R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; PABBISETTY, Kumar Balashanmuga; EWING, William, R.; ZHU, Yeheng; WEXLER, Ruth, R.; PINTO, Donald, J.P.; ORWAT, Michael, J.; SMITH II, Leon, M.; WO2015/116882; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem