Category: pyridine-derivatives

Synthetic Route of 1122-43-6, 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 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

D. [5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid 2,6-dimethyl-pyridin-3-yl ester A mixture of [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid methyl ester (prepared above, 50 mg, 0.17 mmol), 2,6-dimethyl-pyridin-3-ol (21 mg, 0.17 mmol) and DMAP (41 mg, 0.34 mmol) were slurried in dichloromethane. The solution was treated with (3-dimethylamino-propyl)-ethyl-carbodiimide (EDC) (54 mg, 0.28 mmol). After 1 h, thin layer chromatography indicated complete conversion. The reaction mixture was quenched with 10 mL 1 M HCl(aq) and 30 mL dichloromethane. The phases were partitioned, and the aqueous phase extracted with 5 mL dichloromethane. The organic phases were combined and sequentially washed with 10 mL portions of 0.1 M HCl(aq), saturated. NaHCO3(aq) and brine. The organic layer was dried using Na2SO4, filtered and concentrated. The resulting 31 mg of off-white solid was chromatographed over SiO2 (5% methanol/dichloromethane) to yield 21 mg (31%) of the titled compound. ESI-MS z/z 397 (MH+), 395 (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 1122-43-6, 2,6-Dimethyl-3-hydroxypyridine.

Reference:
Patent; UCB SA; US7176310; (2007); B1;,
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. 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine, molecular formula is C6H5ClIN, 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. Product Details of 153034-88-9

General procedure: Table 2, example 4 PdOAc2 (3.4 mg, 0.015 mmol), cesium carbonate (293 mg, 0.900 mmol), and tris(4-methoxyphenyl)phosphine (12 mg, 0.033 mmol) were combined in dioxane (2 mL) and stirred for 15 min at room temperature under an atmosphere of nitrogen. Then 6-chloro-3-iodo-2-methylpyridine (76 mg, 0.30 mmol), O-benzoyl morpholine (69 mg, 0.330 mmol), methylboronic acid(20 mg, 0.33 mmol), and bicyclo[2.2.1]hept-2-ene (28 mg,0.30 mmol) were added as a solution in dioxane (2 mL) to the previously prepared solution of catalyst and base. The reaction was sealed and heated to 100C for 18 h. The reaction mixturewas cooled to room temperature and filtered through a pad of celite eluting with ethyl acetate. The eluent was concentrated and the residue was puried by silica gel chromatography (ISCO 24 gsilica cartridge; 0-30% ethyl acetate in hexanes) to provide4-(6-chloro-2,3-dimethylpyridin-4-yl)morpholine (41 mg, 60%yield) as a colorless oil

With the rapid development of chemical substances, we look forward to future research findings about 153034-88-9.

Reference:
Article; Wilson, Jonathan E.; Tetrahedron Letters; vol. 57; 46; (2016); p. 5053 – 5056;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1018505-59-3, 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 1018505-59-3 as follows.

General procedure: Pd2(dba)3 (86.4mg, 0.09mmol) and Xant-phos (109.2mg, 0.19mmol) were added under N2 to a solution of 154 1E (290.0mg, 0.94mmol), INT-7 (228.6mg, 1.04mmol), and 152 potassium phosphate (400.5mg, 1.88mmol) in 111 1,4-dioxane (10mL). Then the mixture was reacted in the microwave at 150C for 1h. The mixture was cooled to RT, filtered, diluted with water (10mL), and extracted with DCM (10mL×3). The combined organic layers were washed with brine (30mL), dried over anhydrous Na2SO4, concentrated under a vacuum, and purified by preparative thin-layer chromatography to obtain 157 compound 1 (140.3mg; yield, 30%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018505-59-3, its application will become more common.

Reference:
Article; Yin, Lei; Li, Heng; Liu, Wenjian; Yao, Zhenglin; Cheng, Zhenzhen; Zhang, Huabei; Zou, Hui; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 1 – 28;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 121643-44-5, 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 121643-44-5 as follows.

Intermediate 1 : 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5- dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield). 1 H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,121643-44-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100155-73-5 , The common heterocyclic compound, 100155-73-5, name is 1-(2-Pyridyl)-1-propylamine, molecular formula is C8H12N2, 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 8 mL vial charged with imidazole (17.3 mg, 0.26 mmol) and tert-butyl (6-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)(ethyl)carbamate (26.5 mg, 0.051 mmol) in DCM (1ml) was added 1,1′-carbonyldiimidazole (25 mg, 0.153 mmol). The reaction mixture was stirred at room temperature for 5 h, leading to a clear yellow solution. A solution of 1-(pyridin-2-yl)propan-1-amine, 2HCl (21.33 mg, 0.102 mmol) and DIEA (0.045 ml, 0.255mmol) in DMF (1 ml) was added. The vial was capped and the contents stirred at room temperature for 16 h. The reaction mixture was concentrated and the resulting residue redissolved in TFA (1 ml) and stirred at room temperature for 20 minutes. Triethylsilane (0.008 ml, 0.051 mmol) was added dropwise, and the reaction mixture stirred for an additional 5 minutes. The mixture was concentrated, re-dissolved in DMSO (1.5 mL) and submitted for purification by mass-triggered preparative HPLC to afford 1-(3-(ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-(pyridin-2-yl)propyl)urea (4.1 mg, 0.012 mmol, 23.69 % yield) as a white solid.

The synthetic route of 100155-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WILSON, Kevin, J.; WITTER, David, J.; SILIPHAIVANH, Phieng; LIPFORD, Kathryn; SLOMAN, David; FALCONE, Danielle; O’BOYLE, Brendan; MANSOOR, Umar Faruk; LIM, Jongwon; METHOT, Joey, L.; BOYCE, Christopher; CHEN, Lei; DANIELS, Matthew, H.; FEVRIER, Salem; HUANG, Xianhai; KURUKULASURIYA, Ravi; TONG, Ling; ZHOU, Wei; KOZLOWSKI, Joseph; MALETIC, Milana, M.; SHINKRE, Bidhan, A.; THATAI, Jayanth Thiruvellore; BAKSHI, Raman Kumar; KARUNAKARAN, Ganesh Babu; WO2014/52563; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6938-06-3, 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 6938-06-3, name is Butyl nicotinate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The obtained compounds II was dissolved with ethanol (90 mL) and hydrazine hydrate (85percent, 30 mL),then the mixture was heated to reflux for 6 h. After the reaction was completed, ethanol and the excess of hydrazine hydrate were distilled out under a reduced pressure, and a white product was left. The crude product was recrystallized from ethanol to afford white crystals III.

According to the analysis of related databases, 6938-06-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Ning; Sheng, Jun-Feng; Song, Fei; Tong, Yu-Zhu; Wang, Zuo-Xiang; Russian Journal of General Chemistry; vol. 85; 3; (2015); p. 746 – 751;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1018505-59-3 ,Some common heterocyclic compound, 1018505-59-3, molecular formula is C11H18N4, 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: Pd2(dba)3 (86.4mg, 0.09mmol) and Xant-phos (109.2mg, 0.19mmol) were added under N2 to a solution of 154 1E (290.0mg, 0.94mmol), INT-7 (228.6mg, 1.04mmol), and 152 potassium phosphate (400.5mg, 1.88mmol) in 111 1,4-dioxane (10mL). Then the mixture was reacted in the microwave at 150C for 1h. The mixture was cooled to RT, filtered, diluted with water (10mL), and extracted with DCM (10mL×3). The combined organic layers were washed with brine (30mL), dried over anhydrous Na2SO4, concentrated under a vacuum, and purified by preparative thin-layer chromatography to obtain 157 compound 1 (140.3mg; yield, 30%) as a yellow solid.

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. 1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yin, Lei; Li, Heng; Liu, Wenjian; Yao, Zhenglin; Cheng, Zhenzhen; Zhang, Huabei; Zou, Hui; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 1 – 28;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, 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, Quality Control of 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, blongs to pyridine-derivatives compound. Quality Control of 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

Preparation of 3-chloro-4-(2-pyridylmethoxy)aniline from the nitrobenzene product of Example 1 was accomplished with catalytic hydrogenation using platinum on carbon. A typical hydrogenation was done using 6 volumes of THF, 2% by weight of 5% Pt/C (50% water wet), at 25 psi and at 25-30 C. for approximately 4-6 hours. The reaction is slightly exothermic and the temperature will rise to about 30-35 C. Cooling is necessary to maintain the temperature below 30 C. As a specific example, a mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.15 kg, 0.57 mole) and 2% (w/w) of 5% Pt/C (6.0 g) in tetrahydrofuran (0.90 L) was hydrogenated at 25 psi for at least 5 hours. The mixture was filtered through a celite pad and washed with tetrahydrofuran (0.60 L). The filtrate was distilled to a volume of about 0.75 L and ethanol (1.12 L) was added. Distillation was continued to a volume of about 0.75 L and ethanol (2.85 L) was added. The mixture may be used ?as is? in the step of Example 3 below. ; Performing the hydrogenation in isopropyl alcohol (IPA), methanol (MeOH), or ethanol (EtOH) may result in the product being contaminated with late eluting impurity that partially precipitates out on standing in solution. It was found that performing the hydrogenation in a solvent where both the product and starting material are soluble, such as tetrahydrofuran (THF), resulted in greater product purity and required much less solvent. Thus, THF is a preferred solvent for this step. Experimental results showing the effect of different reaction conditions are shown in Table 2. For the larger scale runs, the first aniline intermediate was not isolated (?NI?) before proceeding with the next step. TABLE 2 Hydrogenation to Form First Aniline Intermediate 5% Scale (g) Pt/C** Solvent Vol Time (h) Yield (%) 2.0 1 IPA 50 3 79.6 18 2.0 5 EtOH 60 3100* 10 1 THF 10 4 94.5 7 10 1 EtOH 10 3 95.6 30 1.05 THF 6.5 12 96.3 14 100 2 THF 6 4.5 97.1 400 2 THF 6 4 NI 500 2 THF 6 4 NI 100 2 THF 6 5 NI 150 2 THF 6 5 NI 7 *Solid impurities noted after reaction completion. **percent by weight of starting material.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 956010-87-0 ,Some common heterocyclic compound, 956010-87-0, molecular formula is C7H4F3N3, 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 compound 12 (50 mg, 0.27 mmol), benzylbromide (50 mg, 0.29 mmol) and caesium carbonate (104 mg, 0.32 mmol) was stirred overnight at room temperature in DMF (1.0 mL). It was then diluted with tert-butyl methyl ether and washed with water. The organic layer was dried over sodium sulfate and the solvent was evaporated. The crude product was purified by column chromatography (eluent: cyclohexane/ethyl acetate 3:1) to yield 50 mg (67 %) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta 5.82 (s, 2H), 7.26-7.37 (m, 5H), 7.50 (dd, J=8.2, 4.5Hz, 1H), 8.39 (d, J=8.2Hz, 1H), 8.79 (dd, J=4.5, 1.2Hz, 1H). 13C NMR (125 MHz, DMSO-d6): delta 50.8, 111.4 (q, 1JC,F=1.4Hz), 119.7, 121.4 (q, 1JC,F=269Hz), 127.7, 127.9, 128.7, 129.3, 131.5 (q, 2JC,F=38.6 Hz), 136.2, 149.8, 151.0. HRMS m/z calcd for C14H10F3N3: 277.0827; found: 277.0825.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,956010-87-0, its application will become more common.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 717843-51-1 , The common heterocyclic compound, 717843-51-1, name is 3-Bromo-2-methoxy-4-methylpyridine, molecular formula is C7H8BrNO, 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.

Step 4: To a solution of compound 95 (990 mg, 4.9 mmol) in benzene (33 mL) was added NBS (870 mg, 4.9 mmol) followed by AIBN (40 mg, 0.25 mmol). The mixture was placed in an 80 C oil bath. After six hours, the reaction was diluted with EtOAc, washed with 1 M Na2C03 and brine, dried over MgS04, filtered and concentrated. The crude product was purified by flash chromatography eluting with heptanes/EtOAc (0-10%) to afford compound 96 as an oil (669 mg, 70% pure by NMR). 1H NMR (400 MHz, DMSO-d6) delta 8.14 (d, J = 5.0 Hz, 1 H), 7.22 (d, J = 5.0 Hz, 1 H), 4.68 (s, 2 H), 3.93 (s, 3 H).

The synthetic route of 717843-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem