Category: pyridine-derivatives

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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

To a 4-Chloro-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluorene-7-carboxylic acid tert-butyl ester (3.08 g, 9.40 mmol, 1.05 equiv) in 40 mL of isopropyl alcohol solution was added 3-Chloro-4-(pyridin-2-ylmethoxy)phenylamine (2.10 g, 9.0 mmol, 1 equiv) at rt. 4 N HCl in dioxane (0.1 mL) was added to the reaction mixture to accelerate the reaction. The reaction mixture was heated at 80 C. for 16 h. The mixture was allowed to cool to rt then filtered and washed with IPA (50 mL). DCM (100 mL) and sat. sodium bicarbonate (100 mL) were added to the solid. The mixture was stirred at rt for 1 h before separated the layers. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield 4.50 g of crude material. The crude material was purified by flash chromatography (50% THF/DCM) to yield a light yellow (3.60 g, 6.87 mmol, 76%) as product. 1H-NMR (DMSO-d6) delta 9.32 (broad s, 1H), 8.67 (d, J=4.0 Hz, 1H), 8.40 (s, 1H), 8.27 (s, 1H), 8.05 (t, 1H), 7.79 (d, J=2.7 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.53 (t, 1H), 7.24 (d, J=8.9 Hz, 1H), 5.35 (s, 2H), 4.66 (s, 2H), 3.66 (t, 2H), 3.19 (t, 2H), 1.43 (s, 9H); LCMS RT=3.39 min, [M+H]+=524.0.

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, 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/298297; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 775288-71-6, 1-(6-Nitropyridin-3-yl)piperazine, 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, name: 1-(6-Nitropyridin-3-yl)piperazine, blongs to pyridine-derivatives compound. name: 1-(6-Nitropyridin-3-yl)piperazine

General procedure: A mixture of compounds 8c-8e (26.0 mmol) in acetic acid(10 mL) and methyl alcohol (40 mL) was refluxed, iron (78.0 mmol)was added. The reaction mixture was heated at 60 C for 2 h. Thereaction mixture was poured into saturated aqueous sodium carbonate(100 mL) and extracted with ethyl acetate (3 x 50 mL), thendried over sodium sulfate, filtered and concentrated. The crudeproduct was purified via column chromatography to afford compounds9c-9e.4.1.11.1. 5-(piperazin-1-yl)pyridin-2-amine (9c). White solid. Yield:68%; 1H NMR (DMSO-d6, 400 MHz) delta: 7.62 (d, J = 2.7 Hz, 1H, Pyr-H),7.17 (dd, J = 8.9, 3.0 Hz, 1H, Pyr-H), 6.40 (d, J = 8.8 Hz, 1H, Pyr-H),5.44 (s, 2H, -NH2), 3.43 (t, J = 4.0 Hz, 4H, Pyr-NCH2CH2N), 2.85 (t,J = 4.0 Hz, 4H, Pyr-NCH2CH2N). 13C NMR (DMSO-d6, 100 MHz):delta 163.0, 162.6, 149.4, 146.9, 133.7, 122.1, 120.3, 43.4, 42.6; HRMS(ESI): calcd for C9H14N4O, [(M+H)+], 179.1297, found 179.1285.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,775288-71-6, 1-(6-Nitropyridin-3-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Article; Zhao, Hui; Hu, Xiaoxia; Cao, Kai; Zhang, Yue; Zhao, Kuantao; Tang, Chunlei; Feng, Bainian; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 935 – 945;,
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 175205-81-9, name is 2-Bromo-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H3BrF3N

A 5mL microwave vial flushed with Argon was charged with 2-bromo-4-(trifluoromethyl)pyridine (0.0923 mL, 0.724 mmol), 5-cyclopropyl-2-[3-ethylsulfonyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl )-2-pyridyl]-3-m ethyl-6-(trifluoromethyl)im idazo[4 , 5-c]pyrid in-4-one (Step A, 0.2 g), tetrakis(triphenylphosphine) palladium(0) (0.042 g, 0.036 mmol), potassium phosphate tribasic (0.48 g, 2.17 mmol), toluene (2.9 mL) and water (2.9 mL). The mixture was then heated 30 at 110°C under microwave. The reaction mixture was diluted with water and ethyl acetate then, after separation of the phases, the aqueous phase was extracted two time with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated under vacuum. The residue was subjected to columnchromatography over silica gel, eluting with ethyl acetate cyclohexane. The selected fractions were evaporated to yield the title compound as a white solid (0.11 g). 1H NMR (400 MHz, CDCI3) oe ppm 1.08 (m, 2H), 1.30 (m, 2H), 1.40 (t, 3 H), 3.11 (m, 1 H), 3.85(q, 2 H), 4.09 (s, 3 H), 7.20 (s, 1 H), 7.65 (d, 1 H), 8.11 (s, 1 H), 9.00 (d, 1 H), 9.11 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 175205-81-9.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; MUEHLEBACH, Michel; HALL, Roger, Graham; (106 pag.)WO2017/89190; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82671-06-5, Adding some certain compound to certain chemical reactions, such as: 82671-06-5, name is 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid,molecular formula is C6H2Cl2FNO2, 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 82671-06-5.

To a round-bottomed flask under a N2 atmosphere were added degassed DMF (270 mL), Pd(OAc)2 (0.05 eq, 2.7 g, 11.9 mmol), PPh3 (0.1 eq, 6.2 g, 23.8 mmol), and degassed Et3N (6 eq, 200 mL, 1428.6 mmol). The mixture was stirred for 20 minutes, HCOOH (3 eq, 28 mL, 714.3 mmol) was then added. 5 minutes later, 2,6-dichloro-5-fluoronicotinic acid (50 g, 238.1 mmol) was added. The mixture was stirred at 50 C. The reaction was followed by analysis (1H NMR) of a worked-up aliquot. When all starting material was consumed (24 h), the mixture was cooled to 0 C. and water (500 mL) was added. After 20 minutes, The mixture was filtered through a pad of Celite that was rinsed with water. The mixture was basified to pH 9 with 30% aq. NaOH and washed with EtOAc (2*). HCl (12 N) was added slowly to pH 1 and the solution was saturated with NaCl. The mixture was extracted with EtOAc (3*). The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure to give 37 g (88%) of a beige solid used in the next step without further purification. 1H NMR (DMSO-d6, 300 MHz): delta 8.16 (dd, 1H); 8.58 (d, 1H).

According to the analysis of related databases, 82671-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; US2011/20377; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55676-21-6 ,Some common heterocyclic compound, 55676-21-6, molecular formula is C7H6ClNO, 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 solution of 1-(2-chloropyridin-3-yl)ethanone (B-2) (6 g, 38.6 mmol) and hydrazine (85%, 9.1 g, 154.4 mmol) in pyridine (80 mL) was stirred under reflux overnight. The mixture was cooled to room temperature, concentrated, diluted with water (80 mL) and then extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with brine, dried over Na2S04, and concentrated under vacuo. The resulting residue was used for the next step without furtuer purification. MS (m/z): 134 (M+1 )+

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. 55676-21-6, 1-(2-Chloropyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; WO2011/79804; (2011); 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 17282-03-0, name is 3-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 131.4: 3-Bromo-2-methoxy-5-methyl-pyridine To a solution of 3-bromo-2-chloro-5-methylpyridine (5 g, 24.2 mmol) in MeOH (80 mL) was added a solution of sodium methoxide 5.4M in MeOH (25 mL, 135 mmol) and the mixture was stirred at 65C for 32 h. The resulting suspension was filtered and the mother liquor was concentrated. Et20 and H20 were added and the phases were separated. The organic layer was washed with H20 and brine, dried (MgS04), filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc: 90: 10? 0:100) to afford the title compound. tR: 1.03 min (LC-MS 2).

With the rapid development of chemical substances, we look forward to future research findings about 17282-03-0.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); 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. 106984-91-2, name is 6-Oxo-1,6-dihydropyridine-3-carbaldehyde, molecular formula is C6H5NO2, 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. Application In Synthesis of 6-Oxo-1,6-dihydropyridine-3-carbaldehyde

A solution of 6-hydroxynicotinaldehyde SM 1(192mg, 4 mmol) and (S)-1-cyclopropylethanamine (170 mg, 2 mmol) in DCM (5 mL) and EtOH (5 mL) was added NaBH3CN(620 mg, 10 mmol), then stirred at RT for 16 h. The resulting reaction mixture was quenched withwater and extracted with DCM, dried and evaporated, purified by combiflash (methanol:DCM =1:20) to give compound 1(300mg, 78%). LC-MS: m/z = 193.1 [M+H]

With the rapid development of chemical substances, we look forward to future research findings about 106984-91-2.

Reference:
Patent; ABBVIE INC.; MICHAELIDES, Michael; HANSEN, Todd; DAI, Yujia; ZHU, Guidong; FREY, Robin; GONG, Jane; PENNING, Thomas; CURTIN, Michael; MCCLELLAN, William; CLARK, Richard; TORRENT, Maricel; MASTRACCHIO, Anthony; KESICKI, Edward A.; KLUGE, Arthur F.; PATANE, Michael A.; VAN DRIE, John H. Jr.; JI, Zhiqin; LAI, Chunqiu C.; WANG, Ce; (1190 pag.)WO2016/44770; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113975-22-7, 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. 113975-22-7, name is 2-Fluoro-3-iodopyridine, molecular formula is C5H3FIN, 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.

Di-i-propylamine (260.9 mg, 364.4 muL, 2.578 mmol) was dissolved in dryTHF (1.900 mL) and cooled to -700C. n-BuLi (986.4 muL of 2.5 M, 2.466 mmol) was added slowly dropwise, and the resultant mixture was stirred at 00C for -2 minutes and recooled to -700C. A solution of 2-fluoro-3-iodo-pyridine (500 mg, 2.242 mmol) in dry THF (1.400 mL) was added slowly dropwise and the resultant was stirred at -700C for -2.5 hours. 2,2,2-trifluoroacetaldehyde was added via cannula (bp. is – 200C) and the resultant mixture was stirred at -700C for ~1.5 hours. The reaction was quenched at -700C by the rapid addition of water (~2mL) and the resulting mixture was partitioned with EtOAc. The aqueous phase was extracted with EtOAc (3 x 2OmL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a mobile light brown oil (581.7mg). The resulting mixture was purified by column chromatography (5% EtOAc in DCM, -10OmL silica, loaded in DCM) to give a slightly yellow gum that solidified under high-vacuum to give a light yellow solid (225.2mg, 31% Yield).

According to the analysis of related databases, 113975-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/73300; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)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, HPLC of Formula: C6H2Cl2F3N, blongs to pyridine-derivatives compound. HPLC of Formula: C6H2Cl2F3N

Powdered potassium hydroxide (9.35 g, 0.15 mol, 3 eq. ) is placed together with 70 ml dry DMSO in a 250 ml three-necked-bottom and under dry argon atmosphere the nitromethane (6.1 g, 0.1 mol, 2 eq) solved in 30 ml dry DMSO is added within 30 min slowly with mechanical stirring while cooling with an ice bath to maintain the temperature at 20 C. STIRRING of the reaction mixture at 20C is continued for additional 15 min. Then 2,3-dichloro-5-trifluoromethylpyridine (10.80 g, 0.05 mol, 1 eq. ) is added as one portion without endo-or exothermic reaction. The mixture is heated to 50 C, stirred for 3 h at this temperature and then allowed to cool to room temperature. The dark brown crude product is poured into 500 ml of water, acidified by addition of diluted hydrochloric acid and followed by three extractions with 50 ml ethyl acetate each. The combined organic layers are washed with three 30 ml portions of water and are subsequently dried over anhydrous sodium sulphate. After filtration the solvent is removed at 20C and under 150 mbar reduced pressure. Yield: 9.72 g 3-chloro-2-nitromethyl-5-trifluoromethylpyridine (73.9 % theoretical yield, 91. 4 % purity)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; WO2004/96772; (2004); 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. 110651-92-8, name is 7-Chloro-6-nitrothieno[3,2-b]pyridine, molecular formula is C7H3ClN2O2S, 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. HPLC of Formula: C7H3ClN2O2S

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (156 mg, 0.727 mmol), [(5S)- 5-amino-5,6-dihydro-2H-pyran-2-yl]methyl acetate (129 mg, 0.754 mmol) and N,N- diisopropylethylamine (0.26 mL, 1.5 mmol) in isopropyl alcohol (1.7 mL) was heated at 90 C for 2 h. The reaction mixture was concentrated and purified with flash chromatography to give the desired product (0.21 g 83%). LCMS calculated for CisHieNsOsS (M+ H)+: m/z = 350.1 ; Found: 350.0.

With the rapid development of chemical substances, we look forward to future research findings about 110651-92-8.

Reference:
Patent; INCYTE CORPORATION; SCHERLE, Peggy A.; LIU, Xuesong; WO2015/157257; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem