Pyridine-derivatives

Electric Literature of 677728-92-6 ,Some common heterocyclic compound, 677728-92-6, molecular formula is C6H4FNO, 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 6 Synthesis of 2-fluoro-5-[(E)-2-(4-methoxyphenyl)vinyl]pyridine (1f); Compound 1f was synthesized by Horner-Wadsworth-Emmons.10Synthe -fluoro-5-[(E)-2-(4-methoxyphenyl)vinyl1pyridine (1f)To a solution of diethyl [4-(meththoxy)benzyl]phosphonate (500 mg, 1 .94 mmol) and 6-fluoropyridine-3-carbaldehyde (242 mg, 1 .94 mmol) in DMF (4 mL) was added a solution of potassium tert.butylat (543 mg, 4.8 mmol) in DMF (16 mL). After stirring for one hour the reaction mixture was quenched with saturated aqueous ammonium chloride solution, extracted with dichloromethane, washed with brine and dried over sodium sulfate. The residue was purified by chromatography on silica gel (ethyl acetate in hexane 0 to 50%) to yield 50.6 mg (10.3%) of the title compound.1 H-NMR (400 MHz, CHLOROFORM-d) d = 3.85 (s, 3H), 6.92 (d, 1 H), 6.92 (dd, 1 H), 6.93 (d, 2H), 7.05 (d, 1 H), 7.46 (d, 2H), 7.93 (ddd, 1 H), 8.28 (d, 1 H) ppm. 19F-NMR (376 MHz, CHLOROFORM-d) delta = -70.13 (d, 1 F) ppm. MS ES+ m/z = 230.13 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BERNDT, Mathias; BROCKSCHNIEDER, Damian; HEINRICH, Tobias; BERGER, Markus; WO2011/141515; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 614-18-6, Adding some certain compound to certain chemical reactions, such as: 614-18-6, name is Ethyl nicotinate,molecular formula is C8H9NO2, 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 614-18-6.

EXAMPLE 58 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A solution of 49.2 g (0.32525 mol) ethyl nicotinate and 72 g (1.17 mol) ethanolamine was heated at 70 C. for 60 hours. The excess ethanolamine was removed under reduced pressure and the resulting viscous cream oil was stirred with ether for 48 hours The resulting white solid was removed by filtration, affording 46 g 15 (85 1%) of the title compound melting at 75-78 C.

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. 614-18-6, Ethyl nicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; University of Florida; US5017566; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14529-54-5, Adding some certain compound to certain chemical reactions, such as: 14529-54-5, name is 3,5-Dibromo-1-methylpyridin-2(1H)-one,molecular formula is C6H5Br2NO, 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 14529-54-5.

Example 304c 5-Bromo-3-(5-(2-methoxyethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-1-methylpyridin-2(1H)-one 304c A 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 304b (230 mg, 1.17 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (468.4 mg, 1.76 mmol), Pd2(dba)3 (53.5 mg, 0.0585 mmol), Xantphos (67.6 mg, 0.117 mmol), Cs2CO3 (762.8 mg, 2.34 mmol), and dioxane (20 mL). After three cycles of vacuum/N2 flush, the mixture was heated at 100C for 3 h. Analysis of the reaction mixture by LCMS showed complete conversion to the desired product. It was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 40:1 dichloromethane/methanol to afford 304c as a dark solid (380 mg, 85%). MS-ESI: [M+H]+ 382.2

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. 14529-54-5, 3,5-Dibromo-1-methylpyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
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. 16063-69-7, name is 2,4,6-Trichloropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2,4,6-Trichloropyridine

To a solution of 2,4,6-trichloropyridine (3.64 g, 20.0 mmol) in DMF (20 mL) at 0C were slowly added NaH (60% in mineral oil, 840 mg, 21 mmol) and MeOH (673 mg, 21 mmol). The mixture was stirred at room temperature for 16 h. The mixture was concentrated and partitioned between EtOAc (30 mL) and water (15 mL). The organic extracts were dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with ethyl acetate in hexane (0-5 percent) to afford the title compound (3.0 g, yield: 94%).

The synthetic route of 16063-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEW ERA PHARMA, INC.; XIAN, Jun; (82 pag.)WO2018/106459; (2018); 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.135795-46-9, name is 3-Amino-2-bromo-6-methoxypyridine, molecular formula is C6H7BrN2O, molecular weight is 203.04, as common compound, the synthetic route is as follows.Safety of 3-Amino-2-bromo-6-methoxypyridine

2-Bromo-6-methoxypyridin-3-amine (315.6g, 1.56mol, 1.00wt) was charged to a 20000mL flask under nitrogen followed by tetrahydrofuran (2000mL, 6.3vol) and the reaction mixture cooled to -5oC. Sodium bis(trimetylsilylamide) (1M solution in tetrahydrofuran, 3400mL, 3.42mol, 10.9vol) was added dropwise over 2 hours maintaining the temperature below 5oC. The reaction was warmed to room temperature and stirred for 1 hour. The mixture was re-cooled to 0-5oC and di-tert butyl dicarbonate (372.4g, 1.72mol, 1.18wt) solution in tetrahydrofuran (1600mL) added dropwise over 1 hour. The reaction was left to stir under nitrogen over 16 hours after which the 1H-NMR showed complete reaction. Ethanol (6000mL, 19vol) was added to quench the reaction mixture, stirred for 1 hour and concentrated. Dichloromethane (18000mL, 57vol) and saturated ammonium chloride (3000mL, 9.5vol) were charged to the reaction vessel and stirred for 15 minutes. The layers separated and the aqueous layer extracted with dichloromethane (3x 2000mL, 6.3vol). The combined organic fractions were washed with saturated brine (4000mL, 12.7vol), dried over magnesium sulphate, (315g, 1wt), filtered and concentrated under to give a dark red solid (551.4g).The crude product was purified by dry flash chromatography on silica (2x 2200kg, 8wt) eluting with ethyl acetate:heptanes (1:19; Rf 0.28) collecting 2000mL fractions (TLC visualised at UV 254nm and developed by KMNO4). The product containing fractions were combined and concentrated under reduced pressure to give the title compound 19 (368.6g, 78.2%) as a red solid.1H NMR (400MHz, DMSO): d 1.57 (s, 9H), 3.94 (s, 3H), 6.97 (d, J=8.1Hz, 1H), 7.71 (d, J=8.1Hz, 1H), 8.71 (br s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135795-46-9, 3-Amino-2-bromo-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Article; Badland, Matthew; Devillers, Ingrid; Durand, Corinne; Fasquelle, Veronique; Gaudillire, Bernard; Jacobelli, Henry; Manage, Ajith C.; Pevet, Isabelle; Puaud, Jocelyne; Shorter, Anthony J.; Wrigglesworth, Roger; Tetrahedron Letters; vol. 52; 41; (2011); p. 5292 – 5296;,
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. 188554-13-4, name is 2-Hydroxyisonicotinaldehyde, the common compound, a new synthetic route is introduced below. Safety of 2-Hydroxyisonicotinaldehyde

4-[(E)-2-(4-Fluoro-phenyl)-vinyl]-pyridin-2-ol:To a solution of dieihyl-4-fI?iorobenzyl-phosphonatc (515 mg, 2.09 mmol) in THF ( 10.0 mL) was added potassium tert-buloxide (246 mg, 2.09 mmol). After stirring at 20 0C for 1 h, the mixture was treated with 2-hydroxypyridoaIdehyde (246 mg, 2.00 mmol), and allowed to stir for 3 h at 20 0C. The reaction mixture was quenched with water, and the aqueous phase was extracted with DCM, the combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude oil was purified by column chromatography (DCM to 20%methanol in DCM) gave the desired product 4-[(L)-2-(4-fluoro-phenyO-vinyl]-pyridin-2-ol (32.0 mg, 7.5%, 5: 1 transxis) as white crystal. 1H NMR (400 MHz, CDCh) ?: 7.56 (m, 2H), 7.33 (m, I H), 7.26 (m, IH), 7.08 (m, 2H), 6.87 (m, IH), 6.64 (m, IH), 6.54 (m, IH); ESMS m/e: 216 (M+H)+.

The synthetic route of 188554-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2009/120655; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5223-06-3, 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. 5223-06-3, name is 2-(5-Ethylpyridin-2-yl)ethanol, molecular formula is C9H13NO, 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) To a solution of 2-(5-ethyl-2-pyridyl)ethanol (53.0 g) and 4-fluoronitrobenzene (47.0 g) in DMF (500 ml) was added portionwise under ice-cooling 60% sodium hydride in oil (16.0 g). The mixture was stirred under ice-cooling for one hour, then at room temperature for 30 minutes, poured into water and extracted with ether. The ether layer was washed with water and dried (MgSO4). The solvent was evaporated off to give 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene as crystals (62.0 g, 62.9%). Recrystallization from ether-hexane gave colorless prisms, m.p. 53-54 C.

According to the analysis of related databases, 5223-06-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4687777; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1122-71-0, 6-Methyl-2-pyridinemethanol, 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, Formula: C7H9NO, blongs to pyridine-derivatives compound. Formula: C7H9NO

Diphenylphosphoryl azide (8.02 g, 29.16 mmol) was added to a cooled (0 C.) solution of 6-methyl2-pyridinemethanol (3.00 g, 24.30 mmol) in ether. The resulting mixture was stirred for a few minutes and DBU (4.07 g, 26.73 mmol) was added slowly. The reaction mixture was stirred for 14 hours, decanted into a clean flask and the residue was washed with more ether. The combined organic phases were concentrated to give the crude title azido compound. The crude azide was dissolved in THF:H2O (3:1) and Ph3P (5.77 g, 22.00 mmol) was added, followed by KOH (1.23 g, 22.00 mmol). The reaction mixture was stirred for 14 hours, and then was acidified with concentrated HCl. The resulting solution was washed with Et2O and the aqueous layer was basified with NH3 and extracted with Et2O (3×200 mL). The combined organic extracts were washed with H2O (3×100 mL) and brine (1×100 mL), then dried over MgSO4 and concentrated to give the desired substituted benzylamine. Spectroscopic data: 1H NMR (300 MHz, Acetone-d6) delta 2.52 (s, 3H) 3.91 (s, 2H) 7.04 (d, J=7.61 Hz, 1H) 7.05 (d, J=7.90 Hz, 1H) 7.51 (t, J=7.82 Hz, 1H).

The synthetic route of 1122-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allerghan, Inc.; US2008/194650; (2008); 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. 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

2-Chloro-4, 6-dimethylnicotinonitrile4,6-Dimethyl-2-oxo-l,2-dihydropyridine-3-carbonitrile (5g, 34mmol) was added to phosphorus oxychloride (20ml). The reaction was stirred at reflux for 2 h, after which it was seen complete. Volatiles were removed and the residue triturated with petrol.The resultant solid was filtered off and washed with hexane,and dried to give a pure white solid (5.1g, 90%). deltaH (250 MHz, CDCl3) 2.55 (3 H, s, CH3), 2.57 (3 H, s, CH3),7.09 (1 H, s, ArH); deltac ( 250 MHz, CDCl3) 162.64 (C), 154.39 (C), 152.26 (C), 123.22 (CH), 114.28 (C), 108.31 (C), 24.5 (CH3), 20.54 (CH3).; m/z 189 (M + Na)

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, 769-28-8, 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile.

Reference:
Patent; CYCLACEL LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; WO2008/122767; (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. 13534-89-9, name is 2,3-Dibromopyridine, molecular formula is C5H3Br2N, 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. COA of Formula: C5H3Br2N

General procedure: 2,4-Dibromopyridine (0.236 g, 1 mmol) and phenol (0.094 g, 1 mmol), CuI (19.0 mg, 0.1 mmol), TMEDA (11.6 mg, 0.1 mmol), and cesium carbonate (0.65 g, 2 mmol) were placed in DMSO (5 mL). The reaction was stirred at 110 C under nitrogen atmosphere for 24 h. When the reaction mixture was cooled, the reaction mixture was filtered. The mixture was dissolved with dichloromethane (25 mL). Then the mixture was washed with brine (3×30 mL). The organic phase was dried over sodium sulfate. After evaporation of the solvent, the mixture was subjected to column chromatography with petroleum ether/ethyl acetate (20:1) as eluent to give pure product.

With the rapid development of chemical substances, we look forward to future research findings about 13534-89-9.

Reference:
Article; Zhou, Qizhong; Zhang, Bin; Du, Tieqi; Gu, Haining; Ye, Yuyuan; Jiang, Huajiang; Chen, Rener; Tetrahedron; vol. 69; 1; (2013); p. 327 – 333;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem