Category: pyridine-derivatives

Electric Literature of 89402-42-6, 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 89402-42-6, name is 2,3-Difluoro-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1 Preparation of alpha-anti-methoxyimino-N-methyl-2-(3-fluoro-5-trifluoromethyl-2-pyridyloxy)methylphenyl-acetamide (No. I-1) A suspension of 1.4 g of sodium hydride in 15 ml of dimethylformamide (DMF) was mixed with a solution of 11.1 g of (E) -2-[2-(hydroxymethyl) phenyl]-2-methoxyimino-N-methylacetamide in 120 ml of DMF. The reaction mixture was exposed to ultrasound for about 10 min and subsequently stirred at about 20 to 25 C. for 1 h. A solution of 9.2 g of 2,3-difluoro-5-trifluoromethyl-pyridine in 85 ml of DMF was added dropwise and the mixture was stirred at 22 to 25 C. for about 24 h. The reaction mixture was taken up in 1 l of dilute sodium chloride solution and extracted with methyl tert-butyl ether (MtBE). The combined organic phases were washed with water and dried. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel chromatography (cyclohexane/MtBE=2:1), affording 6.9 g of the title compound as a pale powder of mp. 112-116 C. IR (cm-1): 3380, 1659, 1623, 1498, 1453, 1336, 1272, 1151, 1131, 1040.

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 89402-42-6, 2,3-Difluoro-5-(trifluoromethyl)pyridine.

Reference:
Patent; BASF Aktiengesellschaft; US6372766; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 865156-59-8, 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. 865156-59-8, name is 4-Bromo-6-methylpyridin-2-ol, 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.

Diisopropyl diazocarboxylate (323 mg, 1.60 mmol) was added to a solution of 4- bromo-6-methylpyridin-2-ol (200 mg, 1.06 mmol), methanol (54 ^L, 1.3 mmol) and triphenylphosphine (419 mg, 1.60 mmol) in THF (4.6 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (5 to 10%) to give the title compound (65 mg, 0.32 mmol, 30%).

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 865156-59-8, 4-Bromo-6-methylpyridin-2-ol.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M., Arshad; CIBLAT, Stephane; DERY, Martin; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu; SRIVASTAVA, Sanjay; SHIPPS, Gerald, W.; COOPER, Alan, B.; BRUNEAU-LATOUR, Nicolas; LY, Vu, Linh; (314 pag.)WO2016/196644; (2016); 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. 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, the common compound, a new synthetic route is introduced below. Recommanded Product: 103058-87-3

a) 5-Bromo-2-methoxv-3- (4-methoxv-but-1 (E, Z)-envl)-pvridine; 2. 45 ml of a 1M solution of sodium-bis(trimethylsilyl) amide in tetrahydrofuran are added. to a suspension of 2. 4 mmol (3-methoxy-propyl)-triphenyl-phosphonium bromide [111088-69-8] in 8 mi tetrahydrofuran unter an argon atmosphere at 0C. The reaction mixture is stirred for 30 minutes at 0C and then 1. 6 mmol 5-bromo-2-methoxy-pyridine-3-carbaldehyde [103058-87- 3] are added. The reaction mixture is warmed to room temperature and then diluted with tert- butyl methyl ether. The solution is washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer is dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and identified based on its Rf value

The synthetic route of 103058-87-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); 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. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, the common compound, a new synthetic route is introduced below. COA of Formula: C9H10N2O

The 2-methoxy-4,6-dimethylnicotinic acid required as first starting material is obtained as follows: 97 g (0.6 mole) of 2-methoxy-4,6-dimethylnicotinonitrile and 230 g of solid potassium hydroxide are dissolved in 1000 ml of ethanol and 120 ml of water and the solution is refluxed under nitrogen for 82 hours. The mixture is cooled, the precipitated substance collected by filtration, and the bulk of the ethanol is distilled off from the filtrate in vacuo. The residue is dissolved in 500 ml of water and extracted with methylene chloride. The alkaline aqueous phase is adjusted to pH 3.3 with concentrated hydrochloric acid and the precipitated crude product is collected by filtration. Recrystallisation of this crude product from ethanol yields pure 2-methoxy-4,6-dimethylnicotinic acid (m.p. 210-215 C).

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4089960; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Example 71N-((ls,4s)-4-(2-(4′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)biphenyl-3-yloxy)-5- fluoronicotinamido)cyclohexyl)pyrazolo [ 1 ,5-a] pyridine-2-carboxamide HATU (0.069 g, 0.18 mmol) was added in one portion to N-((ls,4s)-4-aminocyclohexyl)-2- (4′-(((3 S ,5R)-3 ,5 -dimethylpiperazin- 1 -yl)methyl)biphenyl-3 -yloxy)-5 -fluoronicotinamide (0.08 g, 0.15 mmol), pyrazolo[l,5-a]pyridine-2-carboxylic acid (0.024 g, 0.15 mmol) and DIPEA (0.079 niL, 0.45 mmol) in acetonitrile (1 mL) at 250C under nitrogen. The resulting solution was stirred at 25 0C for 10 min. The reaction mixture was concentrated and diluted with EtOAc, and washed sequentially with saturated NaHCO3, saturated brine and water. The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by preparative HPLC on a Waters X-Bridge column using a 95- 5% gradient of aqueous 0.1% TFA in acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford the title compound as a white solid. Yield: 70 mg1H NMR (400 MHz, DMSO) delta 8.61 (d, J= 11.5 Hz, IH), 8.35 (d, J= 6.9 Hz, IH), 8.26 (d, J= 2.8 Hz, IH), 8.07 (dd, J= 3.1, 7.3 Hz, IH), 7.78 – 7.65 (m, 4H), 7.53 – 7.50 (m, 3H), 7.36 (d, J= 7.7 Hz, 2H), 7.30 (t, J= 7.7 Hz, IH), 7.23 – 7.21 (m, IH), 7.02 (t, J= 6.9 Hz, IH), 6.98 (s, IH), 3.38 – 3.28 (m, 2H), 3.10 – 3.04 (m, 2H), 2.56 – 2.44 (m, 4H), 2.23 – 2.14 (m, 2H), 1.84 1.67 (m, 9H), 1.17 (d, J= 10.4 Hz, 6H).MS: [M+H]+=676.3 (calc=676.3411) (MultiMode+)

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, 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); 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. 42182-27-4, name is 2-Amino-4-cyanopyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Amino-4-cyanopyridine

NaN02 (0.99 g, 14.3 mmol) was added in small portions to a well stirred solution of the product of Step B (0.96 g, 8.1 mmol) in a premixed solution of concentrated H2S04 (1 .2 ml) and H20 (1 1 .5 ml) while the temperature of the reaction mixture was kept at ) 0 – 5C. The clear solution became heterogenous with evolution of N2. The mixture was allowed to warm up to room temperature with stirring, than heated on the water bath (reflux) for 30 min and cooled to room temperature. The solid formed was filtered off, washed with H20 and dried in vacuo to give the title product (0.9 g, 92%) as colourless solid. 1 H NMR (DMSO-d6) 8.21 (d, 1 H, J = 2.4 Hz), 7.61 (dd, 1 H, 2.4, 9.6 Hz), 6.38 (d, 1 H, J = 9.6 Hz), 3.3 (broad s, 1 H + 2H20).

The synthetic route of 42182-27-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AKAAL PHARMA PTY LTD; GROBELNY, Damian W; GILL, Gurmit S; WO2014/63199; (2014); 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. 17322-91-7, name is 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one, molecular formula is C7H6N2O, 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 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one

5-hydroxy -1H- pyrrolo [3,2] pyridine (10 mmol)Soluble in 40 ml of dichloromethane solution,Add 10 ml of triethylamine to it,Control temperature below 10 C,Add to the systema solution of 2-chloroacetyl chloride (12 mmol) in dichloromethane,After the addition is completed, return to room temperature.Stir at room temperature for 10 hours,The reaction system was then washed with 50 ml of a 5% aqueous solution of sodium carbonate.The organic phase is dried over anhydrous Na2SO4.After evaporating the solvent,The obtained solid is separated by flash column chromatography,Get 1.9 g light yellow2-Chloro-1-(5-hydroxy-1H-pyrrole[3,2]pyridin-1-yl)-ethanone solid,The yield was 90%.

With the rapid development of chemical substances, we look forward to future research findings about 17322-91-7.

Reference:
Patent; Sang Qi; (10 pag.)CN108218865; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 204378-41-6, 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 204378-41-6, name is Methyl 6-chloro-4-methoxypicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 6-chloro-4-methoxypicolinate 25 (600 mg, 2.98 mmol) and cyclopentylzinc bromide (12 mL of a 0.5 M solution in THF) in dioxane (10 mL) Pd(dppf)Cl2 (25 mg, 30 mol) was added. The mixture was stirred at 75°C for 18 h. The mixture was cooled the rt and the reaction was quenched by carefully adding water (20 mL). The mixture was filtered and the filtrate was extracted with EA (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. The crude product was purified by CC on silica gel eluting with heptane:EA 4:1 to give methyl 6-cyclopentyl-4-methoxypicolinate 30 (580 mg, ~80percent) as a pale yellow oil containing approx. 30percent of cyclopentyl 6-cyclopentyl-4-methoxypicolinate

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 204378-41-6, Methyl 6-chloro-4-methoxypicolinate.

Reference:
Article; Bolli, Martin H.; Lescop, Cyrille; Birker, Magdalena; De Kanter, Ruben; Hess, Patrick; Kohl, Christopher; Nayler, Oliver; Rey, Markus; Sieber, Patrick; Velker, Joerg; Weller, Thomas; Steiner, Beat; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 326 – 341;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 727356-19-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 727356-19-6 as follows.

Potassium pthalimide (1.23 kg, 6.0 mol), potassium carbonate (2.07 kg, 15 mol) were dissolved in DMF (12.5L). A214.1a was added slowly and the reaction stirred at room temperature overnight. TLC analysis indicated disappearance of starting material. The product was filtered to yield A214.1 (2.5kg wet weight- used in next step without further drying).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,727356-19-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 887707-23-5, 2-Hydroxy-5-iodo-3-(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, Formula: C6H3F3INO, blongs to pyridine-derivatives compound. Formula: C6H3F3INO

To a solution of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (4.0 g, 13.8 mmol) in DMF (50 mL), CuCN (2.48 g, 27.7 mmol) was added. The mixture was degassed with 3 vacuum-nitrogen cycles and stirred at 120 C for 16 h. The reaction was cooled to room temperature, poured into water (60 mL), diluted with 3 M HC1 (30 mL) then extracted with EtOAc (3 x 80 mL). The combined organic layers were washed with brine (2 c 60 mL), dried over Na2S04, filtered, and concentrated to give 6-hydroxy-5-(trifluoromethyl)nicotinonitrile (2.5 g, crude) as an oil. 1H NMR (400 MHz, CDCI3): d 8.03 (s, 2H); MS: 189.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; HUDSON, Andrew R.; CHEN, Mi; NAGASAWA, Johnny Y.; (265 pag.)WO2019/241751; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem