Category: pyridine-derivatives

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. 188577-68-6, name is 4,5-Dichloropyridin-2-amine, the common compound, a new synthetic route is introduced below. Safety of 4,5-Dichloropyridin-2-amine

To a 50 ml round-bottomed flask containing 2-amino-4,5-dichloropyridine (0.275 g, 1.65 mmol) and cooled into an ice-bath was added conc. H2SO4 (2.79 g). The reaction mixture was stirred for 3 min and then HNO3 (70%; 0.186 g) was dropwise added. The reaction mixture was stirred at 0 C. (ice-bath) for 7 min, then heated to 55 C. and stirred at this temperature for 1 h, allowed to cool to room temperature, diluted with ice-water (15 ml) and the pH was adjusted to 7.5 with 10% aqueous NaOH. The yellow precipitate was collected by filtration, washed with water and dried in vacuo over P2O5, then absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column. Elution with 2% ethyl acetate in dichloromethane afforded the title compound as a yellow solid (0.090 g, 26%); 1H-NMR (250 Mz, DMSO-d6) 7.39 (s, 2H, NH2), 8.39 (s, 1H, 6-H); LC-MS (ESI, m/z) 6.54 min-208, 210, 212 [(M+H)+, Cl2 isotopic pattern].

The synthetic route of 188577-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17117-17-8, Adding some certain compound to certain chemical reactions, such as: 17117-17-8, name is 3-Bromo-5-ethoxypyridine,molecular formula is C7H8BrNO, 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 17117-17-8.

PREPARATION 169 3-Ethoxy-5-(tri-n-butylstannyl)pyridine A stirred mixture of 3-bromo-5-ethoxypyridine (Rec. Trav. chim., 1948, 67, 377; 930 mg, 4.6 mmol), bis(tri-n-butyltin) (3.46 ml, 6.9 mmol), tri-o-tolylphosphine (420 mg, 1.37 mmol), palladium(II) acetate (78 mg, 0.35 mmol), triethylamine (1.23 ml, 8.84 mmol) and acetonitrile (15 ml), under nitrogen, was heated under reflux for 18 hours, then allowed to cool. The solution was decanted from the black, tarry residue and evaporated under reduced pressure, then the resulting residue flash chromatographed, using an elution gradient of ethyl acetate:pentane (0:100 to 5:95), to yield the title compound (600 mg, 32%) as a colourless oil. delta(CDCl3): 0.90 (t,9H), 1.08 (t,6H), 1.30-1.42 (m,6H), 1.42 (t,3H), 1.58 (m,6H), 4.08 (q,2H), 7.25 (s,1H), 8.17 (s,1H), 8.19 (s,1H).

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. 17117-17-8, 3-Bromo-5-ethoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer INC; US6387931; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1206981-49-8 ,Some common heterocyclic compound, 1206981-49-8, molecular formula is C6H5F3N2O, 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 3-(trifluoromethoxy)pyridin-2 -amine (300 mg, 1.68 mmol) in dichloromethane (8 mL) was added N-bromosuccinimide (450 mg, 2.53 mmol) at 20 C. The reaction mixture was stirred at the same temperature for another 5 min and subsequently concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 15% ethyl acetate in petroleum ether) affording product (220 mg, 51 %): NMR (400 MHz, DMSO- ) delta 8.03 (d, J = 2.0 Hz, 1H), 7.75 – 7.74 (m, 1H), 6.68 (brs, 2H).

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. 1206981-49-8, 3-(Trifluoromethoxy)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 131747-41-6, 2-(Trifluoromethyl)isonicotinic 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, Recommanded Product: 131747-41-6, blongs to pyridine-derivatives compound. Recommanded Product: 131747-41-6

Step 1. (2-(trifluoromethyl)pyridin-4-yl)methanol To a stirred solution of 2-(trifluoromethyl)isonicotinic acid (3.9 g, 20.4 mmol) in 50 mL of THF at 0 C was added a solution of borane (45 mL of a 1.0 M solution in THF, 45 mmol) dropwise over a period of 5 min. The cooling bath was removed and the mixture was stirred at RT for 18 h. The reaction was quenched with the slow addition of water (100 mL). The mixture was extracted with two portions of EtOAc. The EtOAc extracts were combined, washed with brine, dried over MgS04, filtered, and the solvents were removed in vacuo. The crude product was chromatographed on a 40 g S1O2 column using 0-80% EtOAc:hexane over 15 min at 30 mL/min. Fractions containing product were combined and the solvents were removed in vacuo to give the title compound. LCMS m/z = 178.0 (M+H)+.

The synthetic route of 131747-41-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; WILLIAMS, Peter, D.; MCCAULEY, John, A.; BUNGARD, Christopher, J.; BENNETT, David Jonathan; WADDELL, Sherman, T.; MORRIELLO, Gregori, J.; CHANG, Lehua; DWYER, Michael, P.; HOLLOWAY, M. Katharine; CRESPO, Alejandro; CHU, Xin-Jie; WISCOUNT, Catherine; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse, J.; SCHULZ, Jurgen; KEERTIKAR, Kartik, M.; HU, Bin; ZHONG, Bin; JI, Tao; WO2015/138220; (2015); 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. 1193-71-1, name is 4,6-Dimethylpyridin-3-amine. A new synthetic method of this compound is introduced below., Recommanded Product: 4,6-Dimethylpyridin-3-amine

[0096] A solution of methyl-4-bromobenzoate (1) (430 mg, 2mmol) and 4,6-dimethylpyridin-3-amine (2) (250 mg, 2.1 mmol) in toluene (8 mL) was prepared and the flask was closed. It was purged with nitrogen, then 2M solution of Al(CH3)3 in toluene (1.5 mL) was added drop-wise into the reaction mixture. After the addition was finished, the reaction was microwaved for 15 min at 110C. The reaction mixture was cooled down to room temperature, diluted with EtOAc (20mL), washed with 2N solution of NaOH (2 x lOmL) then brine (1×10 mL). Organic phase was collected and dried over a2S04. Column chromatography afforded 4-bromo-N-(4,6-dimethylpyridin-3-yl)benzamide (A) (yield over 80%).

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, 1193-71-1, 4,6-Dimethylpyridin-3-amine.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; CHEN, Shoujun; ZHANG, Junyi; JIANG, Jun; KOWALCZYK-PRZEWLOKA, Teresa; XIA, Zhiqiang; ZHANG, Shijie; WO2013/63385; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52605-96-6, 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 52605-96-6, name is 2-Chloro-3-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2-chloro-3- methoxypyridine (1.55 g, 10.8 mmol, prepared as described in WO2007/123995) in dry THF (30 mL), cooled to -78C, was added 2.5 M nBuLi in hexanes (4.75 mL, 1 1.9 mmol) After 1 hour, a solution of DMF (2.5 mL, 32.4 mmol) in THF (5 mL) was added. After a further 2.5 hours, a saturated aqueous ammonium chloride solution was added and the reaction mixture was allowed to warm to RT. The resultant biphasic mixture was separated and extracted twice with diethyl ether. The combined oraganic phase was washed with water and brine, dried (Na2S04), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si02, gradient 20 to 25 % ethyl acetate in cyclohexane) to afford the title compound (1.42 g, 77%) as a white solid. 1H NMR (300 MHz, CDCI3): delta 10.44 (d, J = 0.8 Hz, 1H), 8.34 (dd, J = 4.9 and 0.8 Hz, 1 H), 7.60 (d, J = 4.9 Hz, 1 H), 4.08 (s, 3H). LCMS (Method A): RT = 2.84 min, [M+H]+ = 172/174.

According to the analysis of related databases, 52605-96-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark Peter; O’DOWD, Colin Roderick; ZHANG, Lixin; TEVITT, Graham Peter; HARRISON, Timothy; BATTACHARYYA, Sumita; ROUNTREE, James Samuel Shane; BURKAMP, Frank; PRICE, Stephen; MACLEOD, Calum; ELLIOTT, Richard Leonard; SMITH, Phillip; BLENCH, Toby Jonathan; DYKE, Hazel Joan; WO2011/33265; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65873-72-5, Adding some certain compound to certain chemical reactions, such as: 65873-72-5, name is 6-Methoxynicotinaldehyde,molecular formula is C7H7NO2, 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 65873-72-5.

4- Aminoresorcinol hydrochloride (3.09 mmol) and triethylamine (3.25 mmol) were dissolved in dry methanol (20 niL). 6-Methoxynicotinaldehyde (3.09) was added and the mixture was stirred overnight. The solvents were removed under reduced pressure, the mixture diluted with EtOAc5 washed with brine (2x), dried (Na2SO4), filtered and evaporated to give 1.31 g as a dark solid. The crude product was taken to the next step without further purification. MS m/z (M+H) 245.

According to the analysis of related databases, 65873-72-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/149030; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 80537-07-1, name is 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid, molecular formula is C14H10N2O2, 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. category: pyridine-derivatives

EXAMPLE 56 STR63 Thionyl chloride (240 mg) was added dropwise to a stirred mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid [compound (I)](320 mg) and N,N-dimethylformamide (one drop) in chloroform (10 ml), and then stirred under reflux for 4 hours. After cooling the mixture, chloroform was evaporated in vacuo to give acid chloride of compound (I). Triethylamine (338 mg) was added to a suspension of the acid chloride of compound (I) in methylene chloride (10 ml) under ice-cooling, and to this suspension a solution of 2-ethylpiperidine in methylene chloride was added dropwise. The mixture was stirred under ice-cooling and stood at room temperature overnight. Saturated sodium chloride aqueous solution (20 ml) was added to the mixture and extracted with chloroform (20 ml). The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (8 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-(2-phenylpyrazolo[1,5-a]pyridin-3-ylcarbonyl)-2-ethylpiperidine (263 mg). mp: 182-183 C. IR (Nujol): 1630, 1600, 1520 cm-1. NMR (DMSO-d6, delta): 0.69 (3H, t, J=7.0Hz), 1.12-1.93 (8H, m), 2.73-3.17 (1H, m), 3.69-4.45 (2H, m) 7.07 (1H, td, J=7.0Hz and 2.0Hz), 7.29-8.00 (7H, m), 8.86 (1H, dd, J=7.0Hz and 1.0Hz). Analysis Calcd. for C21 H23 N3 O: C 75.65, H 6.95, N 12.60. Found: C 75.75, H 7.01, N 12.66.

With the rapid development of chemical substances, we look forward to future research findings about 80537-07-1.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5102878; (1992); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 717843-51-1, 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 717843-51-1, name is 3-Bromo-2-methoxy-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 6 Synthesis of 7-(2-methoxy-4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one 5-(2,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one (100 mg) obtained in Preparation Example 1(5) was dissolved in 1,4-dioxane (4 mL). 3-bromo-2-methoxy-4-methylpyridine obtained in Preparation Example 37 (2) (55.6 mg), Pd(PPh3)4 (10.6 mg), cesium carbonate (179 mg) and water (1 mL) were added to the solution, and the mixture was reacted using a microwave reactor at 130 C. for three hours. The reaction mixture was returned to room temperature and then partitioned by adding ethyl acetate. The organic layer was washed with brine and then dried over magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 30% to 50% to 80%) to give 5-(2,4-dimethoxybenzyl)-7-(2-methoxy-4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one (78 mg). The 5-(2,4-dimethoxybenzyl)-7-(2-methoxy-4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one (78 mg) was dissolved in TFA (1 mL), and the mixture was stirred at 65 C. for two hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was neutralized by adding a saturated aqueous sodium bicarbonate solution. The aqueous solution was extracted with DCM. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 50% to 70% to 80% to 100%) to give the title compound (30 mg). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.15 (s, 3H), 2.15-2.24 (m, 2H), 2.45-2.59 (m, 2H), 3.70 (t, J=12.0 Hz, 2H), 3.87 (s, 3H), 420-4.27 (m, 2H), 5.02-5.11 (m, 1H), 6.89 (d, J=5.1 Hz, 1H), 7.21 (dd, J=8.2 Hz, 1.6 Hz, 1H), 7.34 (d, J=1.6 Hz, 1H), 8.03 (d, J=8.6 Hz, 1H), 8.11 (d, J=5.1 Hz, 1H), 8.31 (s, 1H), 10.57 (brs, 1H). ESI-MS m/z 391 [M+H]+

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 717843-51-1, 3-Bromo-2-methoxy-4-methylpyridine.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 4214-75-9, 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. 4214-75-9, name is 2-Amino-3-nitropyridine. A new synthetic method of this compound is introduced below.

General procedure: To a mixture of 2-aminopyridine (0.5 mmol, 1 equiv), p-TSA (0.4 mmol,0.8 equiv), 1-butylpyridinium bromide (1.5 mmol, 3 equiv) in a 50 mL Schlenk tube were added 1,2-dimethoxyethane (2 mL) under air. Then H2O2 (1.2 mmol, 2.4 equiv) was added. The mixture was stirred at 80C for 24 h. And then the mixture was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the products.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4214-75-9, 2-Amino-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Article; Xu, Tong; Zhou, Wen; Wang, Jing; Li, Xue; Guo, Jun-Wen; Wang, Bin; Tetrahedron Letters; vol. 55; 36; (2014); p. 5058 – 5061;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem