Category: pyridine-derivatives

Synthetic Route of 1149-24-2, 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, 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.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

According to the analysis of related databases, 1149-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 144657-66-9, tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, 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 tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, blongs to pyridine-derivatives compound. Quality Control of tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

General procedure: To a solution of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium chloride in ethanol was added triethylamine and the mixture was stirred at 70 C for 5 min. To the resulting yellow solution were added an aldehyde and a solution of an imine in ethanol. The reaction mixture was stirred in a sealed tube at 50 – 70 C for 18 – 120 h. The reaction mixture was concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel or precipitation.

The synthetic route of 144657-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113209-90-8 ,Some common heterocyclic compound, 113209-90-8, molecular formula is C6H5ClFNO, 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 6′-[3-(dimethylamino)-1-pyrrolidinyl]-4-hydroxy-2/-/-1 ,3′-bipyridin-2-one (150 mg, 0.499 mmol) and triphenylphosphine (327 mg, 1.249 mmol) was treated with (4-chloro-5-fluoro-2-pyridinyl)methanol (81 mg, 0.499 mmol) dissolved in dichloromethane (5 ml). Bis(1 ,1-dimethylethyl) (E)-1 ,2-diazenedicarboxylate (287 mg, 1.249 mmol) was added in two portions, and the reaction mixture was stirred at 250C for 2 h then concentrated under a stream of nitrogen gas. Purification by reverse phase HPLC (1 to 50% gradient) and concentration of the fractions containing product provided a residue. The residue was treated with aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to provide the title compound as a white solid (1 14 mg, 51 %): 1H NMR (400 MHz, CDCI3) delta ppm 8.46 (s, 1 H), 8.06 (d, J = 2.7 Hz, 1 H), 7.56-7.48 (m, 2 H), 7.21 (d, J = 7.6 Hz, 1 H), 6.43 (d, J = 9.0 Hz, 1 H), 6.09 (dd, J = 7.4, 2.5 Hz, 1 H), 5.98 (d, J = 2.7 Hz, 1 H), 5.10 (s, 2 H), 3.95-3.84 (m, 1 H), 3.77-3.65 (br m, 2H), 3.55-3.22 (br m, 2 H), 2.60 (br s, 6 H), 2.47-2.29 (br m, 2 H); ES-LCMS m/z 444 {M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113209-90-8, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/76387; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, molecular formula is C7H6ClNO2, 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 stirred solution of diisopropyl amine (0.82 mL, 5.8 mmol) in anhydrous THF (5 mL) cooled to -15C was added n-butyl lithium (2.5 M in hexanes, 2.3 mL, 5.8 mmol) slowly, maintaining the temperature of the flask between -10C and 0C. The resultant mixture was stirred at room temperature for 15 minutes before being cooling to 0C. The LDA thus formed was added to a rapidly stirred suspension of 2-(2-chloropyridin-3-yl)acetic acid (500 mg, 2.9 mmol) in anhydrous THF (10 mL) at 0C. The resultant bright yellow suspension was stirred at 0C for 15 min. A solution of 2-fluoro-4-iodo-l -isothiocyanatobenzene (814 mg, 2.9 mmol) in anhydrous THF (10 mL) was then added to the reaction mixture (brown suspension) and heated to 65C for 18 hours. The reaction mixture was cooled and the volatiles removed in vacuo. The resultant crude product was redissolved in THF, cooled to 0C and 10% aqueous acetic acid in water (10 mL) was added slowly. Acetonitrile (5 mL) was added slowly until a brown solid developed, the solid was isolated by filtration and washed with ether and acetonitrile to give the title compound. LC/MS: [M+l]+ 415; NMR (300 MHz, DMSO-d6): d 10.74 (s, 1H), 9.21 (s, 1H), 8.36-8.25 (m, 2H), 7.79 (d, J = 1.8 Hz, 1H), 7.68-7.61 (m, 1H), 7.51 (t, J=8.5 Hz, 1H), 7.42- 7.31 (m, 1H).

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 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; KINCAID, John; NEWSAM, John; KISAK, Edward; WOOTTON, Michael; KUSHWAHA, Avadhesh; (364 pag.)WO2020/106304; (2020); 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. 19346-44-2, name is 2-Fluoro-3-nitro-5-methylpyridine, molecular formula is C6H5FN2O2, 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 2-Fluoro-3-nitro-5-methylpyridine

General procedure: The dimethyl derivatives (4,4?, 5,5? or 6,6?) of 3,3?-dinitro-2,2?-azobipyridine were synthesized from the respective hydrazo-derivatives obtained previously from 3-nitro-4(or 5 or 6)-methyl-2-hydrazine-pyridine, respectively. Syntheses of these hydrazo derivatives were very similar to the synthesis of 3,3?-dinitro-2,2?-hydrazobipyridine. Instead of ethanol n-propanol was used and its mixtures were heated at boiling temperature for 30 min in the water bath. 2.52 g (0.015 mol) of 3-nitro-4(or 5 or 6)-methyl-2-hydrazine-pyridine were used to synthesis. The synthesized red-brown needle-like crystals of 4,4?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 255C. The yield was 53.1%. The synthesized brown needle-like crystals of 5,5?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 285C. The yield was 54.0%. The synthesized dark-brown needle-like crystals of 6,6?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 275C. The yield was 51.0%. 1 g of the obtained in this way 4,4?(or 5,5? or 6,6?)-3,3?-dinitro-2,2?-hydrazobipyridine was used to obtain respective azo derivatives in the same way as 3NAP. The synthesized orange needle-like crystals of 4,4?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (4M3NAP) melt with decomposition at 260C. The yield was 74.2%. The synthesized orange needle-like crystals of 5,5?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (5M3NAP) melt with decomposition at 256C. The yield was 77.1%. The synthesized orange powder of 6,6?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (6M3NAP) melt with decomposition at 206C. The yield was 80.3% [51,52,54].

With the rapid development of chemical substances, we look forward to future research findings about 19346-44-2.

Reference:
Article; Kucharska; Hanuza; Lorenc; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 127; (2014); p. 370 – 380;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153034-88-9, Adding some certain compound to certain chemical reactions, such as: 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine,molecular formula is C6H5ClIN, 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 153034-88-9.

A mixture of 2-chloro-4-iodo-3-methylpyridine (250 mg, 986 mumol) (AstaTech, catNo.22441) and boric acid, trimethyl ester (224 muL, 1.97 mmol) in tetrahydrofuran (5.0 mL) was added 2.5 M n-butyllithium in hexanes (789 muL, 1.97 mmol) dropwise at -78 C. The reaction mixture was allowed to warm up to r.t. after 90 min and stirred for another 30 min. The resulting mixture was concentrated and acetonitrile (5 mL) was added. The resulting suspension was filtered through celite then concentrated to give the desired product. LCMS calculated for C6H8BClNO2 (M+H)+: m/z=172.2; found 172.2

According to the analysis of related databases, 153034-88-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Incyte Corporation; Li, Zhenwu; Wu, Liangxing; Yao, Wenqing; (48 pag.)US2017/320875; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1227502-35-3, 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. 1227502-35-3, name is 5-Bromo-3-(hydroxymethyl)pyridin-2(1H)-one, molecular formula is C6H6BrNO2, 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 3: [0901] To a suspension of 5-bromo-3-(hydroxymethyl)pyridin-2(1H)-one 62 (350 mg, 1.72 mmol), Et3N (0.71 mL, 5.16 mmol) and CH2Cl2 (15 mL) was slowly added methanesulfonyl chloride (0.27 mL, 3.43 mmol) at 0 C. under nitrogen. The reaction mixture was allowed to warm to room temperature for 17 h and then water was added. The layers were separated and the aqueous was extracted with CH2Cl2. The organic phase was dried over sodium sulfate and filtered. The solvent was removed and the residue was purified by silica gel chromatography (eluting with 0 to 30% ethyl acetate in hexanes) to provide compound 63 (75 mg, 15%).

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 1227502-35-3, 5-Bromo-3-(hydroxymethyl)pyridin-2(1H)-one.

Reference:
Patent; RVX Therapeutics Inc.; Liu, Shuang; Duffy, Bryan Cordell; Quinn, John Frederick; Jiang, May Xiaowu; Wang, Ruifang; Martin, Gregory Scott; Zhao, He; Molino, Bruce Francis; Young, Peter Ronald; US2014/179648; (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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile, the common compound, a new synthetic route is introduced below. Formula: C6H3ClN2

[Referential Example 114]; 4-Methylthiopyridine-2-carbonitrile; Sodium thiomethoxide (1.01 g) was added to 4-chloropyridine-2-carbonitrile (2.00 g) obtained from Referential Example 113 in N,N-dimethylformamide (20 mL) at 0C, followed by stirring for 2 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane – ethyl acetate), to thereby give the title compound as a solid (1.96 g, 90%).1H-NMR(400MHz,CDCl3)delta: 2.53(3H,s), 7.26-7.27(1H,m), 7.45-7.46(1H,m), 8.45-8.46(1H,m). MS(EI)m/z: 150(M+) .

The synthetic route of 19235-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1591443; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1321612-85-4, 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. 1321612-85-4, name is 3-Fluoro-5-iodopyridin-2-amine, molecular formula is C5H4FIN2, 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.

In a 50-mL round-bottomed flask, the solution of 4-bromobenzenethiol (1.0 g, 5.3 mmol) and 3-fluoro-5-iodo-2-pyridinamine (0.63 g , 2.7 mmol) in DMSO (10 mL) was degassed by purging with argon gas at room temperature for 10 min. K2C03 (2.18 g, 15.9 mmol) and Cul (0.05 g, 0.26 mmol) were added sequentially to the above reaction mixture at room temperature under argon atmosphere. The reaction mixture was heated overnight at 100 C under argon atmosphere. The reaction mixture was cooled to room temperature and filtered through a pad of Celite (diatomaceous earth). The filtrate was diluted with cold water (50 mL) and ethyl acetate (100 mL). The EtOAc layer was separated, washed with water, brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel (100 to 200 mesh) column chromatography (elution 30% EtOAc-hexanes) to give 5-((4-bromophenyl)sulfanyl)-3-fluoro-2-pyridinamine (400 mg) as a white solid.

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 1321612-85-4, 3-Fluoro-5-iodopyridin-2-amine.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60010-03-9, 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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine, molecular formula is C6H4Cl2N2O2, 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.

2,6-Dichloro-4-methyl-3-nitropyridine (Step 31.1;1.17 g, 5.68 mmol) was added at rtto a 2M solution of methylamine in THF and alowed to stir for 30 mm. The reaction mixture was then diluted with EtOAc/water, extracted twice with EtOAc and the combined organic extracts were washed with brine, dried (Na2504) and concentrated. The crude product was purified by flash chromatography (ISCO combi flash; EtOAc/hexanes: 1:4, 5i02) to afford the title compound as a yellow solid. tR: 1.08 mm (LC-MS 2); ESl-MS: 202.0 [M+H]1H NMR (400 MHz, DMSO-d6) 0 ppm 2.39 (5, 3 H) 2.90 (d, J=4.65 Hz, 3 H) 6.73 (5, 1 H) 7.95 (d, J=3.91 Hz, 1 H).

According to the analysis of related databases, 60010-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BOLD, Guido; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; WO2014/191894; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem