Pyridine-derivatives

Synthetic Route of 59782-85-3 , The common heterocyclic compound, 59782-85-3, name is 2,5-Dichloronicotinic acid, molecular formula is C6H3Cl2NO2, 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.

Piperazine A37 may be used in place of piperazine or a substituted piperazine in the above examples. Lithium 2-amino-5-chloronicotinateA solution of 2,5-dichloronicotinic acid (20.2 g, 0.105 mol) in methanol (500 mL) was cooled to 00C and neat thionyl chloride (38 mL, 63 g, 0.525 mol) was added over -30 min. The reaction mixture was stirred at O0C for 1 hour. The cooling bath was removed, the reaction temperature was allowed to warm to room temperature, and the reaction was allowed to stir for an additional 2 days at room temperature. The solvent was removed under reduced pressure to give an off-white residue. The residue was dissolved in Et2O (-500 mL) and the resulting solution was washed successively with saturated aqueous NaHCO3 solution (-300 mL), water (-300 mL), and brine (-300 mL). The organic layer was separated, dried over anhydrous MgSO4, and filtered. Removal of the solvent under reduced pressure yielded methyl 2,5-dichloronicotinate (21.0 g, 97%) as a white solid. EPO Performed in duplicate on identical scales in two pressure vessels, methyl 2,5-dichloronicotinate (4.5 g, 22 mmol) was dissolved in ammonia solution (250 mL, 0.5 M in 1,4-dioxane; 0.125 mol). The pressure vessels were sealed and heated at (85 +/- 5) 0C for 9 days. The two reaction mixtures were allowed to cool to room temperature, then combined and concentrated under reduced pressure to yield a white solid. Dissolution of the solid in 1 :1 acetone-MeOH (-500 mL), followed by adsorption onto silica gel (25 g) and then purification by flash column chromatography (25:10:1 hexane-CH2CI2- Et2O), gave 6.08 g (75%) of methyl 2-amino-5-chloronicotinate. A solution of LiOH*H2O (1.38 g, 33 mmol) in water (33 mL) was added in one portion to a suspension of methyl 2-amino~5~chloronicotinate (6.08 g, 27 mmol) in MeOH (110 mL). The reaction mixture was stirred at 7O0C for 24 hours, and gradually became homogeneous. The solvents were removed under reduced pressure, and after the resulting white solid was dried under vacuum (<1 mmHg) to constant weight, 5.51 g (95%) of lithium 2-amino-5-ch.oronicotinate was obtained. The synthetic route of 59782-85-3 has been constantly updated, and we look forward to future research findings. Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/88840; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 198904-85-7, Adding some certain compound to certain chemical reactions, such as: 198904-85-7, name is tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate,molecular formula is C17H21N3O2, 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 198904-85-7.

[00446] Example 94. Preparation of tert-butyl 2-((2S,3S)-2-hydroxy-4-phenyl-3-{[(benzyloxy) carbonyl]amino}butyl)-2-(4-pyridin-2-ylbenzyl)hydrazinecarboxylate; [00447] To a solution of (l-oxiranyl-2-phenyl-ethyQ-carbamic acid benzyl ester (0.75 g, 2.5 mmol, WO 2005061487) in 2-propanol (10 mL) was added N-(4-pyridin-2-ylbenzyl)hydrazine carboxylic acid tert-butyl ester (0.75 g, 2.5 mmol, WO 2005061487) and the solution was refluxed for 18 hours, after which time it was cooled, solvent was removed in vacuo and the crude residue was purified by column chromatography on silica gel (10% EtOAc/hexane) to give 100 mg, 7% of the compound of this Example. NMR (CDC13) delta ppm 8.62 – 8.76 (m, I H) 7.86 – 8.06 (m, 2 H) 7.65 – 7.82 (m, 2 H) 7.09 – 7.51 (m, 14 H) 5.18 – 5.46 (m, 2 H) 5.00 – 5.10 (m, 2 H) 3.52 – 4.11 (m, 4 H) 2.87 – 3.02 (m, 2 H) 2.72 – 2.87 (m, 1 H) 1.33 (s, 9 H); MS (M + H+) = 597.

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. 198904-85-7, tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/27932; (2008); A2;,
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. 17874-79-2, name is 5-(Methoxycarbonyl)picolinic acid, molecular formula is C8H7NO4, 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. Quality Control of 5-(Methoxycarbonyl)picolinic acid

5-(methoxycarbonyl)pyridine-2-carboxylic acid (100 mg, 0.55 mmol) was dissolved in thionyl chloride (2 mL). The reaction mixture was stirred at ambient temperature for 5 min and a few drops of 7V,7V-dimethylformamide was added. The reaction mixture was stirred at ambient temperature for 5 h. The solvent was removed in vacuo and the crude was added toluene which was evaporated again three times in order to get rid of all thionyl chloride. The crude was dissolved in dry dichloromethane (5 mL) and cooled to 0 0C. A solution of 2,2,2-trifluoroethylamine (176 muL, 2.21 mmol) in dichloromethane (2ml) and slowly added to the reaction mixture. The reaction mixture was stirred at ambient temperature over night. The solvent was removed in vacuo and the crude was partioned between ethyl acetate and IM sodium hydroxide. The organic layer was washed with brine and dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography using a gradient of ethyl acetate in heptane to yield 89 mg (62 %) of the title compound as a white solid; 1R NMR (400 MHz, DMSO-J6) delta ppm 9.50 (t, 1 H), 9.14 (d, 1 H), 8.51 (dd, 1 H), 8.21 (d, 1 H), 4.03 – 4.16 (m, 2 H), 3.93 (s, 3 H); MS (ESI) m/z 263 [M+H+], m/z 261 [M-H+].

With the rapid development of chemical substances, we look forward to future research findings about 17874-79-2.

Reference:
Patent; ASTRAZENECA AB; WO2008/130320; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 26510-52-1, Ethyl 3-oxo-3-(pyridin-2-yl)propanoate, 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: C10H11NO3, blongs to pyridine-derivatives compound. HPLC of Formula: C10H11NO3

3-Oxo-3-pyridin-2-yl-propionic acid ethyl ester (500 mg, 2.59 mmol) and ethylhydrazine oxalate (389 mg, 2.59 mmol) was dissolved in EtOH, and stirred at 80 C. Upon completion, the EtOH was removed and triturated with Et2O to give 2-Ethyl-5-pyridin-2-yl-2H-pyrazol-3-ol (200 mg, 40%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26510-52-1, Ethyl 3-oxo-3-(pyridin-2-yl)propanoate, and friends who are interested can also refer to it.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52378-64-0, 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 52378-64-0, name is (3-Bromopyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Into a 2-L three-necked round-bottom flask, was placed a solution of (3-bromopyridin-2-yl)methanol (50 g, 0.267 mol, 1.0 equiv) in DCM (1.0 L) and 1H-imidazole (36.4 g, 0.534 mol, 2.0 equiv). After the mixture was cooled to 0 C., tert-butyl(chloro)dimethylsilane (48.1 g, 0.320 mol, 1.2 equiv) was added by three batches. The reaction solution was warmed to room temperature and stirred for 4 h. The reaction mixture was diluted with H2O (1.0 L) and extracted with 2×500 mL of DCM. The combined organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column with ethyl acetate/petroleum ether (1:10) to provide the title compound. LCMS (ES) [M+1]+ m/z 302.d

According to the analysis of related databases, 52378-64-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; (115 pag.)US2020/157085; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 137129-98-7, Adding some certain compound to certain chemical reactions, such as: 137129-98-7, name is 6-Chloro-2-methylnicotinic acid,molecular formula is C7H6ClNO2, 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 137129-98-7.

To stirred solution of 6-chloro-2-methyl-pyridine-3-carboxylic acid in ie t-butanol (15mL) was added Et3N (1 .85mL, 13.3mmol) and DPPA (2.86mL, 3.3mmol) and the reaction heated at 90C for 2 hours. The reaction was allowed to cool to room temperature overnight, diluted with water (50ml_) and extracted with EtOAc (3 x 30ml_). The combined organic extracts were washed with water (15ml_), brine (15ml_), dried over MgSC>4 and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography over S1O2 using a gradient of 5-50% EtOAc/isohexane as eluent to give the desired product (1.75g, 71 %) as a white solid. 1H NMR (400 MHz, CDCy delta 8.18 (br. d, 1 H), 7.16 (d, 1 H), 6.26 (br.d, 1 H), 2.48 (s, 3H), 1 .52 (s, 9H).

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. 137129-98-7, 6-Chloro-2-methylnicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CARTER, Neil, Brian; BRIGGS, Emma; KITSIOU, Christiana; LING, Kenneth; MORRIS, James, Alan; TATE, Joseph, Andrew; WAILES, Jeffrey, Steven; WILLIAMS, John; (94 pag.)WO2017/162524; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 372-48-5, 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. 372-48-5, name is 2-Fluoropyridine, molecular formula is C5H4FN, 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.

A I L 2-necked flask was charged with 100 mL of a 2 N solution of lithium diisopropylamide and 400 mL of tetrahydrofuran. This was cooled to “72 C and 2-fluoropyridine (19.42 g, 200 mmol) dissolved in 100 mL of tetrahydrofuran was added dropwise. This was stirred at “70 C for 4 h before dropwise addition of 51 g (200 mmol) of iodine dissolved in 150 mL of tetrahydrofuran. This was stirred for 1 h before being quenched with water. The mixture was diluted with ethyl acetate and aqueous sodium bisulfite. The organic layer was evaporated in vacuo and the product was distilled on a Kugelrohr yielding 2- fluoro-3-iodopyridine (27.0 g, 60.6% yield).

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 372-48-5, 2-Fluoropyridine.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; WU, Yonggang; XIA, Chuanjun; FIORDELISO, James; LAYEK, Suman; ALLEYNE, Bert; DYATKIN, Alexey, Borisovich; ANSARI, Scott; BEERS, Scott; BARRON, Ed; BROOKS, Jason; WO2012/121936; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 86873-60-1, 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. 86873-60-1, name is 5-Chloro-2-picolinic acid, molecular formula is C6H4ClNO2, 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.

To a solution of 5- chloropyridine-2-carboxylic acid (4g, 25.4 mmol) in acetonitrile (250 mL) were added DMAP (0.3g, 2.54 mmol) and TEA (5.3 mL, 38.1 mmol) at 0 C followed by a solution of B0C2O (8.3g, 38.1 mmol) in acetonitrile (50 mL). The resulting light brown solution was warmed up to room temperature and stirred overnight. The solvent was removed in vacuo to afford a white solid which was purified by column chromatography (4:1 Hexanes: EtOAc) to give a white solid (4.5g, 83% yield), mp 86.3-88.3 C. NMR (300 MHz, DMSO-cfo 5 8.75 (dd, J = 2 and 1 Hz, 1H), 8.1 1 (dd, J = 8 and 2 Hz, 1H), 8.00 (dd, J = 8 Hz, 1H), 1.55 (s, 9H).

According to the analysis of related databases, 86873-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; HAMMOCK, Bruce, D.; HWANG, Sung, Hee; WECKSLER, Aaron, T.; MORISSEAU, Christophe; WO2012/112570; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55304-90-0, (2,6-Dichloropyridin-3-yl)methanol, 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: 55304-90-0, blongs to pyridine-derivatives compound. Recommanded Product: 55304-90-0

To a solution of (2,6-dichloropyridin-3-yl)methanol (1.0 g, 5.62 mmol) in CH2C12 (10 ml) was added Dess-Martin reagent (4.8 g, 11.24 mmol) at 26C. After addition the mixture was stirred at room temperature for 2 h. Once the reaction was complete, the mixture was then quenched by adding 5% aqueous Na2S203 and stirred for 30 min. The resulting mixture was extracted with CH2C12 (2×30 ml). The combined organic layers were washed with saturated Na2S203 solution (50 ml), brine (30 ml), dried over Na2S04 and concentrated to give the title compound which was used in next step without further purification. (800 mg, Yield 80%). 1H NMR (400MHz, CDC13): 10.38 (s, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55304-90-0, (2,6-Dichloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100695; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89488-29-9, 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. 89488-29-9, name is 2-Bromo-4-methoxypyridine, molecular formula is C6H6BrNO, 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.

Preparation 55 To a suspension of 2-bromo-4-methoxypyridine (1.21 g), 4-chlorophenylboronic acid (1.21 g) and tetrakis(triphenylphosphine)-palladium (372 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (7.74 ml). The mixture was stirred at 80 C. for 12 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. 2-Propanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methoxypyridin-2-yl)-chlorobenzene (1.03 g). 1H-NMR (CDCl3): delta3.91(3H,s), 6.78(1H,dd,J=5.7 Hz,2.4 Hz), 7.19(1H,d,J=2.4 Hz), 7.42(2H,d,J=8.6 Hz), 7.90(2H,d,J=8.0 Hz), 8.51(1H,d,J=5.7 Hz)

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 89488-29-9, 2-Bromo-4-methoxypyridine.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6521643; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem