Pyridine-derivatives

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 14294-11-2, name is 1-(Pyridin-2-yl)thiourea. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 14294-11-2

According to Scheme 3 Step 4: A solution of 2-bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)propan-1-one (23.8 mmol, 7.70 g) and of 1-(pyridin-2-yl)thiourea (26.2 mmol, 4.02 g) in EtOH (200 mL) was stirred under reflux overnight. The reaction was quenched with water (200 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield a brown solid. The resulting crude product was purified by flash chromatography over silica gel using DCM/AcOEt (98:2) as eluent to yield after evaporation 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methyl-N-(pyridin-2-yl)thiazol-2-amine (20.7 mmol, 7.80 g, 87%) as a beige solid.LC (Zorbax SB-C18, 3.5 mum, 4.6×50 mm Column): RT=2.29 min; MS m/z ES+=378.

With the rapid development of chemical substances, we look forward to future research findings about 14294-11-2.

Reference:
Patent; Bolea, Christelle; Calanire, Sylvain; US2010/144756; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 754230-78-9 ,Some common heterocyclic compound, 754230-78-9, molecular formula is C12H11BrN2O, 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 85A Ethyl 8-(benzyloxy)-6-bromo-2-methylimidazo[1,2-a]pyridine-3-carboxylate Under argon, 200 g (0.72 mol) of 3-(benzyloxy)-5-bromopyridine-2-amine Example 84A, 590 g (3.58 mol) of ethyl 2-chloroacetoacetate and 436 g 3 A molecular sieve were suspended in 6 l of ethanol and boiled at reflux for 72 h. The reaction mixture was filtered off through kieselguhr and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate 9:1, then 6:4) and the product fractions were concentrated. This gave 221 g (79% of theory) of the target compound. LC-MS (Method 17): Rt=1.31 min MS (ESpos): m/z=389 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=1.36 (t, 3H), 2.58 (s, 3H), 4.32-4.41 (m, 2H), 5.33 (s, 2H), 7.28-7.32 (m, 1H), 7.36-7.47 (m, 3H), 7.49-7.54 (m, 2H), 8.98 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,754230-78-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 34160-40-2, name is 6-Bromo-2-pyridinecarboxaldehyde. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromo-2-pyridinecarboxaldehyde

Step 1: Synthesis of 2-bromo-6-(difluoromethyl)pyridine (0396) 3.81 g (23.6 mmol) of (diethylamino)sulfur trifluoride were added with ice cooling to a mixed solution of 2.00 g (10.8 mmol) of 6-bromopicolinaldehyde and 40 ml methylene chloride. After completion of the addition, said reaction mixture liquid was stirred for 2 hours with ice cooling. After completion of the stirring, the reaction was stopped by addition of 30 ml of saturated aqueous sodium hydrogen carbonate solution, and said reaction liquid was extracted with methylene chloride (2×30 ml). The organic layer obtained was washed with water, then dried with anhydrous sodium sulfate, and the solvent distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (n-hexane:ethyl acetate=10:0 to 8:2), and 1.87 g of the desired compound were obtained as a white solid. (0397) 1H-NMR (CDCl3, Me4Si, 300 MHz): delta 7.73-7.58 (m, 3H), 6.58 (t, 1H, J=56 Hz).

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, 34160-40-2, 6-Bromo-2-pyridinecarboxaldehyde.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; NAKAYA, Yoshihiko; MASUZAWA, Yoshihide; FURUHASHI, Takamasa; MIYAKADO, Yuuki; HOTTA, Hiroyasu; INABA, Masamitsu; (76 pag.)US2016/221998; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83004-14-2, 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. 83004-14-2, name is 2-Bromo-4-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

Example 59 A mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (950 mg, 3 mmol), (prepared as described for the starting material in Example 24), 2-bromo-4-bromomethylpyridine (765 mg, 3 mmol) and potassium carbonate (2.38 g 17 mmol) in DMF (10 ml) was heated at 80 C. for 2 hours. The mixture was allowed to cool, poured into water and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent removed by evaporation and azeotroped with toluene. The residue was triturated with ethyl acetate/hexane and the solid product collected by filtration, washed with ethyl acetate/hexane and dried to give 7-((2-bromo-4-pyridyl)methoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline (647 mg, 44%). m.p. 210-212 C. 1 H NMR Spectrum: (DMSOd6) 3.98(s, 3H); 5.40(s, 2H); 7.25(s, 1H); 7.30(d, 1H); 7.50(s, 1H); 7.50(d, 1H); 7.55(m, 2H); 7.74(s, 1H); 7.86(s, 1H); 8.35(br s, 1H); 8.42(d, 1H); 9.56(s, 1H) MS – ESI: 489 [MH]+ Elemental analysis: Found C 52.0 H 3.2 N 11.2 C21 H15 N4 O2 BrClF Requires C 51.5 H 3.1 N 11.4%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83004-14-2, its application will become more common.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 57266-69-0, 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. 57266-69-0, name is 3-Chloropicolinic acid. A new synthetic method of this compound is introduced below.

To a solution of 3-chloropicolinic acid (20.006 g, 126.98 mmol) in toluene (200 mL) was added thionyl chloride (23.2 mL, 37.8 g, 317 mmol, 2.5 equiv.) and a catalytic amount of DMF (10 drops) and the mixture was heated at reflux for 1 h. After cessation of the gas evolution, the mixture was cooled and all volatiles were removed in vacuum to obtain to obtain the title compound (24.38 g, quant.) as a crude product, which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57266-69-0, 3-Chloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; DESHMUKH, Prashant; KOeRBER, Karsten; KAISER, Florian; KORDES, Markus; DICKHAUT, Joachim; NARINE, Arun; BANDUR, Nina Gertrud; VEITCH, Gemma; CULBERTSON, Deborah L.; NEESE, Paul; GUNJIMA, Koshi; WO2013/24006; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 35905-85-2, 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. 35905-85-2, name is 2-Bromonicotinic acid. A new synthetic method of this compound is introduced below.

Step 2: Methyl 2-bromonicotinate (G2); A solution of of CH2N2 (4 eq.) in Et2O (1 M) was added dropwise to a solution of 2- bromonicotinic acid in THF (0.5 M) at RT. The reaction mixture was stirred at room temperature overnight, then quenched by dropwise addition of AcOH (4 eq.). The organic phase was washed with water and brine and dried (MgSO4). Evaporation of the solvent yielded (75%) the title compound which was used in the next step without further purification. 1H NMR (300MHz, CDCl3, 300K) delta 8.47 (IH, dd, J= 4.8 Hz, 2.1 Hz), 8.07 (IH, dd, J= 7.8 Hz, 2.1 Hz), 7.35 (IH, dd, J= 7.5 Hz, 4.5 Hz), 3.93 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,35905-85-2, 2-Bromonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/112832; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72716-87-1 , The common heterocyclic compound, 72716-87-1, name is 2-Methoxyisonicotinaldehyde, molecular formula is C7H7NO2, 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.

Nitrosonitric acid (1 mL) was added dropwise to a solution of 2-methoxypyridine-4-formaldehyde (137 mg, 1.0 mmol) in trifluoroacetic anhydride (2 mL) at room temperature. The reaction mixture was stirred at 25 C for 3 days, and then was poured into ice-water mixture, followed by the addition of saturated sodium carbonate solution to adjust the pH value to exceed 10. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried and concentrated. The resulting residue was dissolved in toluene (5 mL), and toluene-p-sulfonic acid (5 mg) and glycol (105 mg, 1.7 mmol) were added. The reaction mixture was heated to reflux and reacted overnight. After cooled, the mixture was washed with saturated sodium carbonate solution and brine, dried, and concentrated under vacuum. The resulting residue was dissolved in methanol (10 mL), added Pd/C catalyst (20 mg), and introduced into hydrogen gas. The reaction system was stirred for 2 h under 1 atm hydrogen, then filtered to remove the catalyst, and concentrated under vacuum to remove the solvent. The residue was purified by column chromatography to obtain the title compound (15 mg, 8 %). 1H NMR (DMSO-d6): delta 9.31 (1H, s), 8.56 (1H, s), 7.42 (1H, s), 7.34 (1H, s), 6.55 (1H, s), 5.43 (2H, s), 5.30 (2H, s), 4.02 (3H, s), 2.04-1.91 (2H, m), 0.90-0.85 (3H, m).

The synthetic route of 72716-87-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Li, Yuliang; WANG, Huting; ZHU, Yan; WANG, Zhe; ZHANG, Hui; ZHAO, Ruiyu; HUANG, Yuanyuan; WANG, He; PENG, Yong; LUO, Hong; XIAO, Dengming; CAO, Shousong; HAN, Yongxin; EP2862571; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866545-96-2, 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 866545-96-2, name is 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of l-(5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone (50 g, 0.21 mol) in tetrahydrofuran (1400 mL) was added sodium hydride (8.8 g, 0.22 mol, 60 %) at 0 C. After the mixture was stirred for 1 h at 0 C a solution of 4-methylbenzene-l-sulfonyl chloride (48.3 g, 0.25 mol) in tetrahydrofuran (300 mL) was added dropwise at 0 C. The resulting mixture was warmed up to RT and stirred overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate (3 xlOOO mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo affording crude l-(5-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone as yellow solid (75 g, yield: 90 %), which was used for the next step without further purification: NMR (400 MHz, DMSO-d6): delta 8.884 (s, 1H), 8.532-8.573 (m, 2H), 8.054-8.075 (d, J = 12 Hz, 2H), 7.442-7.463 (d, J = 8.4 Hz, 2H), 2.578 (s, 3H), 2.347 (s, 3H

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 866545-96-2, 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone.

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

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. 58584-63-7, name is (6-Methoxypyridin-3-yl)methanol, the common compound, a new synthetic route is introduced below. Safety of (6-Methoxypyridin-3-yl)methanol

j0259j To a stirred solution of (6-methoxypyridin-3-yl)methanol (75 mg, 0.54 mmol) in dichloromethane (2 mL) under nitrogen was added triethylamine (0.083 mL, 0.59 mmol) followed by methanesulfonyl chloride (0.044 mL, 0.57 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was partitioned between dichioromethane (10 mL) and water (10 mL). The organic extract was dried over sodium sulfate, filtered and concentrated to give the title compound 88 mg (quantitative yield) as a yellow oil.Tr(METCR1278) = 1.63 mm, (ESj (M-J-H) 1581160.

The synthetic route of 58584-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; KISELYOV, Alex; BROWN, Christopher, John; GALAN, Sebastien, Rene Gabriel; PRIME, Michael, Edward; GILES, Paul, Richard; GADOULEAU, Elise, Luciennen Paulette; KRUeLLE, Thomas, Martin; CLARK-FREW, Daniel; JOHNSON, Peter, David; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; COE, Samuel; HAYES, Sarah; (271 pag.)WO2016/33445; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 26218-75-7, 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.26218-75-7, name is Methyl 6-bromopicolinate, molecular formula is C7H6BrNO2, molecular weight is 216.03, as common compound, the synthetic route is as follows.

Into a 2000-mL 4-necked round- bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 6-bromopyridine-2-carboxylate (43.2 g, 199.97 mmol, 1.00 equiv), tetrahydrofuran (700 mL). This was followed by the addition of bromo(methyl)magnesium (150 mL) dropwise with stirring at 0C. The resulting solution was stirred overnight at room temperature. The mixture was then quenched by the addition of 200 mL of water. The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 35 g (81%) of 2-(6-bromopyridin-2-yl)propan-2- ol as yellow oil.

The chemical industry reduces the impact on the environment during synthesis 26218-75-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (0 pag.)WO2019/165204; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem