Category: pyridine-derivatives

Electric Literature of 18653-75-3, 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 18653-75-3, name is 2-(1H-Imidazol-2-yl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Na2MoO4·2H2O (0.847g, 3.5mmol), 2-pyim (0.0065g, 0.040mmol), Mo powder (0.06g, 0.60mmol), ZnCl2 (0.136g, 1mmol), H3PO3 (0.02g, 0.25mmol), tetrabutylammonium hydroxide (TBAOH, 0.2mL, 0.3mmol) and distilled water (9.0mL) were stirred for 1h under the room temperature. An aqueous solution of 2molL-1 HCl was added into the mixture and the pH value was adjusted to 3.8. After that, the mixture continues to stir for an another 2h. Finally, the product was transferred to 25 Teflon-lined antoclave and was heated to 180C for 3days before cooled down to the room temperature. In the end, dark-red crystals 2 were collected and dried in air (yield: 62.45%). Elemental analysis: calculated: C, 14.11; H, 1.36; N, 6.17; found: C, 14.01; H, 1.28; N, 6.58.

According to the analysis of related databases, 18653-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Han, Ye-Min; Cheng, Wei-Wei; Cao, Jia-Peng; Yang, Mu-Xiu; Hong, Ya-Lin; Kang, Run-Kun; Xu, Yan; Inorganica Chimica Acta; vol. 498; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 82671-06-5, 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 82671-06-5 as follows.

Example 16A (^-Sjdelta-Difluoro^-hydroxy^^i^Kfl.SloxathioIoS^-clpyridin-theta- ylmethyl)amino]-l-piperidinyl}methyI)-4,5-dihydro-7H-pyrrolo[3,2,l-^]-l?5- naphthyridin-7-one dihydrochloride(a) 2-Chloro-5-fluoro-6-(methyloxy)-3-pyridinecarboxylic acidA solution of 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (51.12g, 243 mmol) in methanol (400 ml) was treated with sodium methoxide in methanol (25% w/v, 100 ml, 535 mmol) and the mixture heated to reflux for 4 hours. The cooled mixture was treated with water (400 ml) and acidified to pH2 with aqueous hydrochloric acid (2M) then concentrated to ca 400 ml. Filtration, washing with water and drying in vacuo over P2O5 for 18h afforded the product as a white solid (32.65g, 65%). MS (+ve ion electrospray) m/z 208 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,82671-06-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/71936; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14150-94-8, Adding some certain compound to certain chemical reactions, such as: 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one,molecular formula is C6H5N3O5, 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 14150-94-8.

A mixture ofbenzyl (3-oxocyclohexyl)carbamate (247 mg, 0.999 mmol) and 1-methyl- 3,5-dinitropyridin-2(1H)-one (300 mg, 1.507 mmol) in ammonia/MeOH (1M, 6 mL) was microwaved at 90 C for 30 mm to provide a blackish-red solution. Eleven more samples of the same composition were run under the same conditions. The twelve samples were combined and evaporated under reduced pressure. The residue was partitioned between DCM (300 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 50% EtOAc in hexanes) provided a mixture of benzyl (3-nitro- 5,6,7, 8-tetrahydroquinolin-7-yl)carbamate and undesired regioi somer benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-5-yl)carbamate as a pale yellow gum. The mixture was used without further purification. MS (ESI, m/z): 213 [M+H]t; j00424J A solution of benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (2.64 g, 8.07 mmol) in ethanol (110 mL) was treated with tin(II) chloride dihydrate (9.10 g, 40.3 mmol) and conc. HC1 (1 mL), then stirred at 80 C for 75 mm. The solution was allowed to cool, then was concentrated under reduced pressure to about 15 mL. The sample was made basic (pH 9) by addition of saturated aqueous NaHCO3; about midway through, the sample was diluted with DCM (100 mL). The mixture was triturated, then filtered, and the filter cake was washed with DCM (50 mL). The filter cake was triturated and sonicated in MeOH (200 mL), then the mixture was filtered. The slightly cloudy filtrate was filtered through Celite 545, then concentrated to provide a yellow solid. Purification by silica gel chromatography (0 to 15% MeOH in DCM) provided a mixture of benzyl (3-amino-5,6,7,8-tetrahydroquinolin-7-yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification. MS (ESI, m/z):298 [M+H]t; 1004251 A sample of benzyl (3-amino-S ,6, 7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (1.25 g, 4.22 mmol) was treated with ACN (17 mL). The material was cooled on a dry ice / ethylene glycol bath (approximately -10 to -15 C) and PTSA monohydrate (1.61 g, 8.45 mmol) was added. After stirring 10 mm, a solution of potassium iodide (1.05 g, 6.33 mmol) and sodium nitrite (0.436 g, 6.32 mmol) in water (3.4 mL) was added dropwise over 20 mm. The dry ice bath was replaced with an ice bath, and the reddish-brown mixture was stirred at 0 C for 3 h 40 mm. The solution was diluted with EtOAc (50 mL), cooled on an ice bath and treated with saturated aqueous NaHCO3 until basic (pH 8-9). The organic layer was removed and the aqueous layer was extracted once more with EtOAc (50 mL). The combined organics were washed sequentially with water and brine (50 mL each), dried (Na2504), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 23% EtOAc in hexanes) provided a mixture of benzyl (3-iodo-S,6,7,8-tetrahydroquinolin-7- yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification.MS (ESI, m/z): 409 [M+H]; 1004261 A mixture of t-BuXPhos Pd G4 (76.3 mg, 94.4 tmole), benzyl (3-iodo-5,6,7,8- tetrahydroquinolin-7-yl)carbamate and regioisomer (605.0 mg, 1.482 mmol), tert-butyl piperazine-1-carboxylate (553.5 mg, 2.97 mmol), and sodium tert-butoxide (257.1 mg, 2.68 mmol) was sealed in a 40-mL vial. The atmosphere was evacuated and replaced with nitrogen, three times. Dioxane (15 mL) was added and the solution was stirred at ambient temperature for three days. Material at the same stage from a previous run (from 40.7 mg, 0.100 mmol iodo starting material) was added. The mixture was diluted with EtOAc (100 mL), treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 87% EtOAc in hexanes) provided a mixture of tert-butyl 4-(7-(((benzyloxy)carbonyl)amino)-5 ,6,7, 8-tetrahydroquinolin-3 – yl)piperazine-1-carboxylate and regioisomer as a yellow foam. The mixture was used without further purification. MS (ESI, m/z): 467 [M+H].

According to the analysis of related databases, 14150-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); 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.1597-33-7, name is 2-Fluoropyridin-3-amine, molecular formula is C5H5FN2, molecular weight is 112.11, as common compound, the synthetic route is as follows.SDS of cas: 1597-33-7

To a solution of the corresponding amines (1 equiv.) in dichloromethane was added pyridine (1 equiv.) and phenyl chloroformate (1 equiv.) at 0 C. Stirring was continued for 2 h followed by the addition of the scaffold amine (1 equiv.) and DMAP (0.2 equiv.). The reaction mixture was refluxed overnight. After cooling, water was added and extracted with dichloromethane. The pooled organic fractions were brine washed, dried, concentrated and purified by Reverse Phase Prep-HPLC to provide compounds A6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1597-33-7, 2-Fluoropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; POPOVICI-MULLER, Janeta; SALITURO, Francesco Gerald; SAUNDERS, Jeffrey Owen; TRAVINS, Jeremy; YAN, Shunqi; WO2014/62511; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 944401-56-3 ,Some common heterocyclic compound, 944401-56-3, molecular formula is C6H4BrF3N2, 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 5-bromo-4-(trifluoromethyl)-pyridin-2-amine (6, 7.47 g, 31 mmol) and DMAP (366 mg, 3.0 mmol) in CH2Cl2 (120 mL) were added triethylamine (8.6 mL, 62 mmol) followed by di-tert-butyl dicarbonate (7.6 mL, 33 mmol) at 0 C. The reaction mixture was stirred at rt for 5 h. The organic solution was washed with water and brine, dried over MgSO4. The organic solvent was removed, and the residue was purified by silica gel chromatography with 1:20 EtOAc/PE to give 7 as white solid (6.67 g, 92% yield, Rf = 0.56 in 1:10 EtOAc/PE). 1H NMR (400 MHz, CDCl3) delta: 9.07 (s, 1H), 8.58 (s, 1H), 8.42 (s, 1H), 1.58 (s, 9H). 13C NMR (100 MHz, CDCl3) delta: 152.3, 152.1, 151.7, 139.4 (q, J = 33 Hz), 121.7 (q, 1JCF = 275 Hz), 110.9 (q, J = 6 Hz), 108.9, 82.3, 28.3. MS (ESI + APCI) m/z: 341.0 [M-H]-, 343.0 [M+H]+.

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. 944401-56-3, 5-Bromo-4-(trifluoromethyl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Peng, Wei; Tu, Zheng-Chao; Long, Zi-Jie; Liu, Quentin; Lu, Gui; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 644 – 654;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13958-98-0, Adding some certain compound to certain chemical reactions, such as: 13958-98-0, name is 3-Bromo-4-cyanopyridine,molecular formula is C6H3BrN2, 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 13958-98-0.

4-cyano-3-bromopyridine in a 300 mL three-necked flask(3.9 g, 21.3 mmol), 3-fluoro-4-tributylstannylpyridine (9.05 g, 23.4 mmol),Add CuI (406 mg, 2.1 mmol) and add dioxaneIt was dissolved in (106 ml).To this was added Pd (PPh3) 4 (739 g, 0.64 mmol), and the mixture was heated and stirred overnight while being refluxed. After cooling to room temperature, concentrate andThe obtained residue was purified by column chromatography to obtain 3.9 g (19.6 mmol) of bipyridine compound 5 (yield 92%).

According to the analysis of related databases, 13958-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nippon Catalyst Co., Ltd.; Kuwata, Kenji; Hasegawa, Munehiro; (29 pag.)JP2019/73486; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 405174-97-2, 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.405174-97-2, name is 3-Bromo-2-formylpyridine, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.

A mixture of B6.1 (480 mg, 2.58 mmol ) in MeOH(10 mL) and THF(5 mL) was cooled to 0 oC , NaBH4 (390 mg, 10.32 mmol) was added in portions .The mixture was stirred for 4 h, then concentrated, and diluted with water(30 mL), extracted with DCM (30 mL × 3). The organic layer was washed with brine (30 mL), dried over Na2SO4, concentrated to give the title compound (400 mg, 82%) as a white solid. LC-MS: [MH]+ = 188.0.

Statistics shows that 405174-97-2 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-formylpyridine.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue; ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (193 pag.)WO2017/221092; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 156270-06-3, 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. 156270-06-3, name is 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid. A new synthetic method of this compound is introduced below.

A mixture of trans-3- (2- (1- (4-amino) cyclohexyl) ethyl)-7-cyano-2, 3,4, 5-tetrahydro- 1 H 3-benzazepine (103 mg, 0.35 mmol), 3-pyrrol [2,3-b] pyridyl carboxylic acid (56 mg, 0.35 mmol), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (67 mg, 0.35 mmol) and 1-hydroxybenzotriazole (20 mg, 0.15 mmol) in dichloromethane (8 ml) was shaken at room temperature for 16 h. The reaction mixture was washed with saturated aqueous sodium bicarbonate (4 ml). The resulting precipitate was collected by filtration, washed with water (2 x 10 ml) and dried to give the title compound (81 mg, 0.18 mmol, 53percent) as a colourless solid. Mass spectrum (API+) : Found 442 (MH+). C27H31N5O requires 441. 1 H NMR (DMSO-d6) 8 : 1.02 (2H, m), 1.15-1. 45 (6H, m), 1.81 (4H, m), 2.50 (5H, m), 2.91 (4H, m), 3.73 (1H, m), 7.14 (1H, m), 7.32 (1H, d, J = 8 Hz), 7.57 (2H, m), 7.73 (1H, d, J = 8 Hz), 8.16 (1H, m), 8.25 (1H, m), 8.42 (1H, m), 12.03 (1H, br s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156270-06-3, 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/94835; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 552331-00-7, Adding some certain compound to certain chemical reactions, such as: 552331-00-7, name is 4-Iodopyridin-2-amine,molecular formula is C5H5IN2, 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 552331-00-7.

Library Protocol 3 To a 0.2M solution of 5-(4,4, 5,5-tetramethyl- 1, 3,2-dioxaborolan-2-yl)-2-[( 1 -{[4-(trifluoromethoxy) phenyl]acetyl}piperidin-4-yl)oxy]benzamide (Preparation 14, 500 p L, 100 pmol) in DMF was added a 0.2M solution of compounds of formula (IV) (500 pL, lOOpmol) in DMF with argon purging. A 2M solution of cesium carbonate (100 pL, 200 pmol) in degassed water was added followed by tetrakis(triphenylphosphine)palladium (0) (5.7 mg, 5 pmol) and the reaction was heated to 130C under microwave irradiation for 15 minutes. The reaction wascooled and concentrated in vacuo. The residue was dissolved in DMSO (1 mL) and purified using preparative HPLC using one of the Purification Methods (PM) below:

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. 552331-00-7, 4-Iodopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19798-77-7, 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 19798-77-7 as follows.

In the second step, the first step product 2- [1- (2-cyanoethyl) -1H-indol-3-yl] acetic acid was added to dichloromethane (20 mL)EDCI (1.27 g) was added at room temperature,Stirring dissolved;3-Chloro-4-aminopyridine (0.9 g) was added,DMAP (0.15 g),The reaction was stirred at room temperature for 3 h.(10 mL) was stirred for 10 min, and the organic phase was added with saturated brine (10 mL) for 10 min.The organic phase was separated by column chromatography and eluted with ethyl acetate-petroleum ether (1: 3) to give a pale yellow solidN- (3-chloropyridin-4-yl) -2- [1- (2-cyanoethyl) -1H-indol-3-yl] acetamide (0.8 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19798-77-7, its application will become more common.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Shi Jiangong; Guo Ying; Xu Chengbo; Chen Qing; Chen Minghua; Ba Mingyu; Zhu Chenggen; Tang Ke; Jiang Jiandong; Guo Jiamei; Guo Qinglan; Lin Sheng; Yang Yongchun; (44 pag.)CN107151223; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem