Month: April 2022

Electric Literature of 868551-30-8 , The common heterocyclic compound, 868551-30-8, name is Methyl 4-methyl-5-nitropicolinate, molecular formula is C8H8N2O4, 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 mixture of methyl 4-methyl-5-nitropyridine-2-carboxylate (3.5g, 17.8mmol), dimethylformamide dimethylacetal (DMF-DMA) (3.6ml, 1.5eq) in acetonitrile (35mL) was heated in a microwave at 140C for 20 min. The solvent was removed. The residue (5.1 g) was carried onto the next step without further purification.

The synthetic route of 868551-30-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2005/103003; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 709652-82-4, 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.709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.

To 2-amino-5-bromonicotinonitrile (0.785 g, 3.96 mmol), triethylamine (0.553 mL, 3.96 mmol) and 4-dimethylaminoyridine (20 mg, 0.164 mmol) in CH2CI2 (25 mL) was added di-fe f-butyl- dicarbonate (2.16 g, 9.91 mmol) and the resulting mixture stirred at room temperature for 18h. Evaporated to dryness in vacuo and triturated in heptane (25 mL) for 72h. The resulting precipitate was filtered and washed with heptane (10 mL) to give imidodicarbonic acid, 2-[5- bromo-3-(cyano)-2-pyridinyl]-, 1 ,3-bis(1 , -dimethylethyl) ester as a beige solid (1.1 g, 70% yield). 1 H NMR (400 Mhz, CDCI3, 298K) 1.51 (s, 18H) 8.16 (d, 1 H) 8.77 (d, 1 H). LCMS: [M+H]+=398/400.1 , Rt (4)= 1.43 min.

The chemical industry reduces the impact on the environment during synthesis 709652-82-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131747-62-1, 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. A new synthetic method of this compound is introduced below.

To a solution of 165 (100 mg, 0.518 mmol) in toluene 15 ml was added 66 (99.7 mg, 0569 mmol). PTSA (196.8 mg 1.03 mmol) was added to the reaction mass, which was then stirred at 120 C. for 12 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, which was used in the next step with out 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

Electric Literature of 1206968-92-4 , The common heterocyclic compound, 1206968-92-4, name is (5-Bromo-3-fluoropyridin-2-yl)methanol, molecular formula is C6H5BrFNO, 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.

[00186] To a solution of 69 (90 mg, 0.44 mmol) in anhydrous CH2C12 (1 mL) was added sulfonyl chloride (0.2 mL) at rt under N2. The mixture was stirred at reflux for 3 h. The mixture was concentrated under reduced pressure to afford crude chloride q (HC1 salt, 100 mg, 100%) as a yellow solid, which was used for the next step directly without further purification. LC-MS tR = 0.796 mm in 5-95 AB_1 .5 mm chromatography (Welch Xtimate MK RP-18e 25-2mm), MS (ESI) m/z 223.6 [M+H].

The synthetic route of 1206968-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2014/179564; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 623942-84-7 ,Some common heterocyclic compound, 623942-84-7, molecular formula is C7H8BrNO2, 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 mixture of (3-bromo-6-methoxypyridin-2-yl)methanol (1.9 g, 8.7 mmol) in dichloromethane (100 mL) was added N-bromosuccinimide (1.8 g, 10 mmol) and triphenylphosphine (2.6 g, 10 mmol) under an ice bath condition and nitrogen atmosphere. The reaction mixture was stirred at rt for 3 h and then concentrated in vacuo, the residue was purified by column chromatography on a silica gel eluted with PE/EA (v/v = 30/1) to give the title compound as light yellow liquid (1.4 g, 57 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,623942-84-7, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; WANG, Xiaojun; YANG, Xinye; WU, Junwen; XIONG, Shaohui; PAN, Shengqiang; CAO, Shengtian; ZHANG, Yingjun; (121 pag.)WO2018/24224; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22282-70-8 ,Some common heterocyclic compound, 22282-70-8, molecular formula is C5H3FIN, 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 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (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,22282-70-8, 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; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); 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 1256825-86-1, name is Methyl 1H-pyrrolo[2,3-b]pyridine-6-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C9H8N2O2

To a suspension of methyl 1H-pyrrolo[2,3-b]pyridine-6-carboxylate (200 mg; may be prepared as described in intermediate 169) in MeOH (10 ml) was added lithium borohydride (74 mg) and the reaction mixture was stirred at room temperature for 30 min. Lithium borohydride (74 mg) was added and the mixture was heated at 5O0C for 15 hr. Lithium borohydride (148 mg) and the mixture was heated at 5O0C for 24 hr. Lithium borohydride (small amounts portionwise over six hours, approximately 300 mg) was added and the mixture was heated at 5O0C for 72 hr. Lithium borohydride (small amounts portionwise over six hours, approximately 300 mg) was added and the mixture was heated at 5O0C for 24 hr. The reaction mixture was cooled and left at RT for 2 days. The solvent was evaporated and the residue dissolved in aqueous hydrochloric acid (2 N, 20 ml). The aqueous was washed with EtOAc (2 x 30 ml). The aqueous was basified with 12.5 N aqueous sodium hydroxide to pH 14 and then extracted with DCM (3 x 25 ml). The organic layer was dried over magnesium sulfate, filtered and evaporated to give an off-white solid (42mg). This was purified by MDAP to afford the title compound (32 mg) as a white solid. 1H NMR (CD3OD) delta: 4.74 (2H, s), 6.45 (1 H, d), 7.22 (1 H, d), 7.33 (1 H, d), 7.97 (1 H, d). Retention time 0.57 min (LC/MS method 4).

With the rapid development of chemical substances, we look forward to future research findings about 1256825-86-1.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); 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. 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., COA of Formula: C8H7BrN2

A solution of 19 (200 mg, 0.952 mmol) and 27 (162.8 mg, 0.952 mmol) in acetonitrile was added Na2CO3 (201.6 mg, 1.904 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (38.8 mg, 0.0476 mmol) was added to the reaction. The reaction mass was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90 C. under sealed conditions overnight, then allowed to cool to RT and diluted with chloroform. The organic layer was filtered through Celite and concentrated to get the crude, which was purified through flash chromatography by using 100-200 silica mesh. The compound was eluted at 2% methanol chloroform as off-white colour solid 28.

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, 1111637-94-5, 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); 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. 156072-84-3, name is 5-Chloro-2-cyano-3-methylpyridine. A new synthetic method of this compound is introduced below., Product Details of 156072-84-3

To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH 5. ON (110 ml, 550 mmol). The resulting mixture was refluxed at 90 C for 18 h. After cooling to RT, the reaction mixture was conentrated, diluted with water and the pH of the solution was adjusted to 4 by addition of 5N HC1. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2X). The aqueous layer was again acidified with 5N HC1 to pH 4 and extracted with EtOAc (2X). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a high vac oven at 40 C for 12 h to give the title compound 5-chloro-3-methylpicolinic acid (24.1 g, 140 mmol, 89 % yield). LC/MS (ESf ) m/z = 172.0 (M+H)+; H NMR (400 MHz, CHLOROFORM -J) delta ppm 11.29 (br. s., 1 H), 8.41 (d, J=1.76 Hz, 1 H), 7.73 (d, J=1.76 Hz, 1 H), 2.75 (s, 3 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, 156072-84-3, 5-Chloro-2-cyano-3-methylpyridine.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89415-54-3 ,Some common heterocyclic compound, 89415-54-3, molecular formula is C6H8BrN3, 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 mixture of the 5-bromo-/V-methyl-3-nitro-2-pyridinamine (1.14 g, 4.21 mmol assumed). and ammonium chloride (1.103 g, 20.62 mmol) in EtOH^O (8.5 mL of a 1 :1 solution) was stirred as iron (1 .152 g, 20.62 mmol) was added. The mixture was heated to reflux for ~ 2 hours. The mixture was allowed to cool to room temperature then diluted with EtOH and filtered through Celite. The filtrate was concentrated to yield a black tar which was diluted with EtOH then concentrated three times. The residue was slurried in EtOH then filtered. The filtrate was concentrated to yield a black solid which was dissolved in pyridine (15.1 mL). N, N dimethylaminopyridine (0.060 g, 0.49 mmoL) was added followed bybenzenesulfonylchlonde (0.63 mL, 4.91 mmol). The resulting mixture was stirred for one hour under a nitrogen atmosphere. The mixture was then concentrated. The residue diluted with EtOAc, washed with water two times, then saturated NaHC03 followed by brine, dried(Na2S0 ) and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes). Fractions containing the product were combined and concentrated to yield A/-[5-bromo-2-(methylamino)-3-pyridinyl]benzenesulfonamide (0.859 g, 2.51 mmol 60% over 3 steps) as a grey solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (br. s., 1 H) 7.94 (br. s., 1 H) 7.75 – 7.64 (m, 3 H) 7.62 – 7.55 (m, 2 H) 6.92 (d, J=2.3 Hz, 1 H) 6.25 (br. s., 1 H) 2.68 (d, J=4.5 Hz, 3 H) LCMS: m/z 344 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89415-54-3, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna, Lindsey; BOTYANSZKI, Janos; DICKERSON, Scott, Howard; DUAN, Maosheng; LEIVERS, Martin, Robert; MCFADYEN, Robert, Blount; MOORE, Christopher, Brooks; REDMAN, Aniko, Maria; SHOTWELL, John, Bradford; TAI, Vincent, W.-F.; TALLANT, Matthew, David; XUE, Jianjun; WO2012/37108; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem