Pyridine-derivatives

Electric Literature of 67367-24-2, 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. 67367-24-2, name is Methyl 4-hydroxynicotinate, molecular formula is C7H7NO3, 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.

Step 2 Methyl 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a, 10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) nicotinate (3R,4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a,10b-dimeth yl-8-dihydromethylene-1H-naphtho[2,1-d][1,3]dioxin (300.00 mg, 729.20 umol) was dissolved in N,N-dimethylformamide (5.00 mL), and potassium carbonate (201.57 mg, 1.46 mmol) and methyl 4-hydroxynicotate (223.34 mg, 1.46 mmol) were added successively and then stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction was quenched by adding 30 mL water and then extracted with ethyl acetate (30.00 mL). The organic phase was successively washed with water (30 mL) and saturated brine (30 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by column chromatography (silica, petroleum ether/ethyl acetate=1/1) to give methyl 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) nicotinate (a yellow oil, 200 mg, yield: 56.71%). 1H NMR (400 MHz, CDCl3) 8.89 (s, 1H), 8.51 (d, J=6.0 Hz, 1H), 6.80 (d, J=5.8 Hz, 1H), 4.88 (s, 1H), 4.66-4.50 (m, 2H), 4.24-4.14 (m, 1H), 4.03 (d, J=11.3 Hz, 1H), 3.98-3.85 (m, 4H), 3.54-3.39 (m, 2H), 2.42 (d, J=12.3 Hz, 1H), 2.27 (dq, J=3.0, 13.2 Hz, 1H), 2.16-2.04 (m, 2H), 1.95-1.87 (m, 3H), 1.83-1.76 (m, 1H), 1.72-1.67 (m, 3H), 1.54 (td, J=7.4, 19.3 Hz, 4H), 1.49-1.38 (m, 3H), 1.36 (s, 3H), 1.30-1.24 (m, 3H), 0.79 (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 67367-24-2, Methyl 4-hydroxynicotinate.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 639091-75-1, Methyl 2-(Boc-amino)isonicotinate, 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, 639091-75-1, blongs to pyridine-derivatives compound. Formula: C12H16N2O4

Compound 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaC12 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight atambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20 mL of NaC1 (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,639091-75-1, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174064; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 917391-98-1, 5-Fluoro-2-oxo-1,2-dihydropyridine-3-carbaldehyde, 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: 917391-98-1, blongs to pyridine-derivatives compound. Recommanded Product: 917391-98-1

(b) 1 -Ethyl-5- fluoro-2-oxo-pyridine-3-carbaldehvde K2Ctheta3 (0.830 g, 6.00 mmol) was added to a solution of 5-Fluoro-2-oxo-pyridine- 3-carbaldehyde (0.424, 3.00 mmol) in dry DME (10 mL). Ethyl iodide (0.303 mL, 3.75 mmol) was added dropwise while the reaction was heated to reflux. After 8 hours the reaction was cooled to RT, filtered and evaporated. Purification using flash chromatography (heptane/EtOAc, 10-100%) gave 0.249 g (49 %) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,917391-98-1, 5-Fluoro-2-oxo-1,2-dihydropyridine-3-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2006/135323; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1256810-26-0, Adding some certain compound to certain chemical reactions, such as: 1256810-26-0, name is 6-Bromo-3-methoxypicolinic acid,molecular formula is C7H6BrNO3, 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 1256810-26-0.

To a solution of (4-chlorophenyl)methanamine (610 mg, 4.31 mmol), 6-bromo-3- methoxypicolinic acid (1.0 g, 4.31 mmol) and triethylamine (1.31 g, 12.9 mmol) in DCM (10 mL) was added dropwise T3P (2.74 g, 8.61 mmol) at 0C. Five minutes later, TLC indicated the reaction was complete, and the mixture was suspended in water and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (1.3 g, yield: 87%) without further purification. -NMR (DMSO-i, 400 MHz) delta 8.98 (t, J = 6.0 Hz, 1H), 7.69 (d, J = 8.8 Hz, 1H), 7.58 (d, J = 8.8 Hz, 1H), 7.39-7.43 (m, 2H), 7.33 (d, J = 8.4 Hz, 2H), 4.22 (d, J = 6.4 Hz, 2H), 3.84 (s, 3H). MS (M+H)+: 355 / 357.

According to the analysis of related databases, 1256810-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); 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.685115-77-9, name is 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide, molecular formula is C11H13Cl2N3O, molecular weight is 274.15, as common compound, the synthetic route is as follows.Computed Properties of C11H13Cl2N3O

To a suspension of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (75 mg, 0.27 mmol), 1 ,5-dimethyl-4-pyrazole boronic acid pinacol ester (76 mg, 0.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (16 mg, 5mol%) in acetonitrile (3 ml.) was added 0.5 M solution of sodium carbonate (0.77 ml_, 0.38 mmol). The mixture was heated to in a microwave reactor at 150 0C for 45 min. Once cooled the reaction was concentrated in vacuo and dry loaded onto silica. The crude product was purified by flash column chromatography on silica gel (CH2CI2, EtOH, 97:3-80:20, biotage 25+S) to furnish the title compound as a clear colourless oil (24 mg, 26%), LC-MS (ESI, 4 min) Rt 1.49 min, m/z 334 (100%, [M+H]+); m/z (ESI) Ci6H20N5OCI requires 333.1356, found [M+H]+ 333.1354.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,685115-77-9, 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; McDONALD, Edward; BLAGG, Julian; PICHOWICZ, Mark; CRUMPLER, Simon Ross; WO2010/41054; (2010); 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. 851484-95-2, name is 2-Chloro-5-fluoronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloro-5-fluoronicotinaldehyde

2-chloro-5-fluoronicotinaldehyde (20 g, 125 mmol) was taken up in THF (150 ml) at 0 C. (R)-2-Methylpropane-2-sulfinamide (16.71 g, 138 mmol) was added followed by dropwise additionof titaniumtetraethanolate (22.88 ml, 150 mmol). The reaction mixture was stirred while warming to RT. After 3 hours the reaction mixture was cooled to 0 C, and 150m1 of brine was added and stirred for 20 minutes. The mixture was filtered through Celite. The aqueous layer was separated and discarded. The organic layer with dried over Na2SO4 and the solvent was removed to give(S ,Z)-N-((2-chloro-5-fluoropyridin-3 -yl)methylene)-2-methylpropane-2- sulfinamide (32 g, 122 mmol, 97 % yield), which was carried on without further purification. LCMS: 263 M+H.

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, 851484-95-2, 2-Chloro-5-fluoronicotinaldehyde.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil, Jr; KIM, Joseph, L.; (91 pag.)WO2017/87778; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 184368-74-9, 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate, 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: 184368-74-9, blongs to pyridine-derivatives compound. Recommanded Product: 184368-74-9

C. 1-boc-1,2,3,6-Tetrahydro-4-pyridinecarboxylic Acid To a stirred solution of methyl 1-Boc-1,2,3,6-tetrahydro-4-pyridinecarboxylate (2.22 g, 9.2 mmol) in methanol (10 mL) was added 1.0 N aqueous sodium hydroxide (25 mL). After stirring for 2 h, the solvent was removed in vacuo. The residue was partitioned between diethyl ether and water, and the layers were separated. The aqueous phase was acidified to pH 2.5 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium chloride, dried (magnesium sulfate), filtered, and concentrated in vacuo to give 1.62 g (78%) of the title compound as a white solid. 1H-NMR; IS-MS, m/e 226.1 (m-1)-; Analysis for C11H17NO4: Calcd: C, 58.14; H, 7.54; N, 6.16; Found: C, 57.41; H, 7.48; N, 6.19.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,184368-74-9, 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US6635657; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2369-19-9, 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. 2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, 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.

Example 38A 2-fluoro-4-iodo-5-methylpyridine A solution of diisopropylamine (7.0 mL, 50.0 mmol) in THF (100 mL) at -78 C. was treated with 2.5M n-butyllithium in hexanes (20 mL, 50.0 mmol), stirred for 15 minutes, treated dropwise with a solution of 2-fluoro-5-methylpyridine (5.55 g, 50.0 mmol) in THF (20.0 mL), stirred for 4 hours, treated slowly with a solution of iodine (12.7 g. 50.0 mmol) in THF (50 mL), quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/diethyl ether to provide 7.24 g (61%) of 2-fluoro-3-iodo-5-methylpyridine.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62150-46-3, 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 62150-46-3, name is 4-Bromopicolinamide. This compound has unique chemical properties. The synthetic route is as follows.

The flask was charged with (2-(2-chlorophenyl)-8-methylquinolin-3-yl)methan- amine (100.0 mg, 0.354 mmol), obtained from A-1216 US PSP, procedure D, 4- bromopicolinamide (92 mg, 0.460 mmol), diisopropylethylamine (0.080 ml, 0.460 mmol) and 1-butanol (2.0 ml ) and sealed. The mixture was subjected to microwave at 180C for 4hrs. After cooled to room temperature, the mixture was concentrated, and the residue was diluted with MeOH. The solution was purified by HPLC, 25%-45% of B in 35min. The collected fractions were concentrated and dissolved in CH2Cl2, neutralized by washing with aq. NaHCO3. The CH2Cl2 layer was dried, concentrated and gave 4-((2-(2-chlorophenyl)-8-methylquinolin- 3-yl)methylamino)picolinamide, 1H-NMR (MeOD) delta 8.21 (s, 1 H), 8.01(d, J= 5.6 Hz, IH), 7.71 (d, J= 8.0 Hz, IH), 7.41-7.62 (m, 6 H), 7.20 (d, J= 2.4 Hz, IH), 6.50 (dd, J= 5.6,2.4 Hz, IH) 4.42 (d, J= 11.0 Hz, IH), 4.27 (d, J= 11.0 Hz, IH), 2.73 (s, 1 H). Mass Spectrum (ESI) m/e = 403.1 (M + 1).

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 62150-46-3, 4-Bromopicolinamide.

Reference:
Patent; AMGEN INC.; WO2008/118455; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1019021-85-2, 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.1019021-85-2, name is 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5FN2O2, molecular weight is 180.1359, as common compound, the synthetic route is as follows.

Oxalyl chloride (10 mL, 1 10 mmol) was added dropwise to a stirred suspension of 6- fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (24b) (2 g, 1 1 mmol) and catalytic amounts of DMF in dichloromethane (20 mL). After 5 hours, the solvent was evaporated and the solid was suspended in dry DCE (20 mL) and added to a stirred solution of 3- amino-4-methylbenzonitrile (1 .45 g, 1 1 mmol) and DIEA (6 mmol) in DCE (1 0 mL) at 0 C. After the addition, the reaction was heated at 60 C for 5 hours. The mixture was subjected to standard aqueous work and silica purification to give N-(5-cyano-2- methylphenyl)-6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (39) as a solid. 1 H NMR (400MHz, c/6-DMSO) delta 10.14 (s, 1 H), 9.45 (dd, J = 5.2, 2.0 Hz, 1 H), 8.62 (s, 1 H), 7.90 – 7.87 (m, 2 H), 7.68-7.63 (m, 1 H), 7.53 (d, J = 8.0 Hz, 1 H), 2.37 (s, 3H). MS m/z 295.1 (M+1 ) +. NH2OH (5 mL, 16.1 mmol) was added in one portion to a stirred suspension of N-(5- cyano-2-methylphenyl)-6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (39) (0.95 g, 3.23 mmol). The resulting suspension was heated at 60 C overnight and then cooled to 0 C. The product, (Z)-6-fluoro-N-(5-(N’-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1 ,2- a]pyridine-3-carboxamide (40) was collected by filtration. MS m/z 328.1 (M+1 ) +.

Statistics shows that 1019021-85-2 is playing an increasingly important role. we look forward to future research findings about 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem