Category: pyridine-derivatives

Electric Literature of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile. A new synthetic method of this compound is introduced below.

2-Chloro-5-cyanopyridine (1 .5 g) is dissolved in hydrazine (6 mL) at r.t. and an exothermic reaction occurs and a solid precipitate forms. Water is added and the solid is filtered off washing with water and is dried by suction to give the hydrazine intermediate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33252-28-7, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1192813-41-4, 2-(Difluoromethoxy)-5-nitropyridine, 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, Application In Synthesis of 2-(Difluoromethoxy)-5-nitropyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-(Difluoromethoxy)-5-nitropyridine

2-Difluoromethoxy-5-nitro-pyridine obtained in Step A (1.6 g) was treated with iron (5 g) and concentrated hydrochloric acid (0.23 ml) in ethanol (15 ml) and water (2.5 ml) at 800C for 20 minutes. Filtration over Celite and evaporation of the solvent afforded 6- difluoromethoxy-pyridin-3-yl-amine (1.4 g) as an orange solid. IH NMR (400 MHz, CDCI3) 3.51 (br s, 2H), 6.89 (d, IH), 7.23 (d, IH), 7.44 (dd, IH), 7.80 (d, IH).

The synthetic route of 1192813-41-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; CASSAYRE, Jerome Yves; CORSI, Camilla; MAIENFISCH, Peter; WO2010/9968; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65515-39-1, Adding some certain compound to certain chemical reactions, such as: 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile,molecular formula is C9H10N2O, 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 65515-39-1.

(a) 4-(3-hydroxypent-4-en-l-yl)-2-methoxy-6-methylnicotinonitrile and 4-(2- (hydroxymethyl)but-3-en- -yl)-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (2.8 g, 17.26 mmol) in THF (85 mL) was added LHMDS (1 M in THF, 18.13 mL, 18.13 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction mixture turned an orange color. The mixture was stirred at 0 C for 50 min, 2-vinyloxirane (1.703 mL, 20.72 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature for 4 h. The reaction mixture was quenched with saturated aqueous ammonium chloride (40 mL) and the layers were separated, the aqueous layer was extracted with EtOAc (3x). The combined organics were concentrated and the residue was adsorbed onto silica, and purified by flash chromatography (CombiFlash, 0-40% EtOAc in hexane, 80 g column) to afford 4-(3-hydroxypent-4-en-l-yl)-2-methoxy-6-methylnicotinonitrile (512 mg, 2.204 mmol, 12.8% yield) as a yellow oil. LC-MS(ES) m/z = 233.3 [M+H]+. Also isolated was 4-(2-(hydroxymethyl)but-3-en-l-yl)-2-methoxy-6- methylnicotinonitrile (1.08 g, 4.65 mmol, 26.9% yield) as a yellow oil. LC-MS(ES) m/z = 233.3 [M+H]+.

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. 65515-39-1, 2-Methoxy-4,6-dimethylnicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (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.1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate, molecular formula is C21H17FN6O2, molecular weight is 404.4, as common compound, the synthetic route is as follows.Recommanded Product: Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate

A 5-L, three-neck, round-bottom flask was equipped with an overhead stirrer, a thermocouple, a 500-mL addition funnel and a nitrogen-inlet adapter. The flask was dried with a heat gun under a flow of nitrogen to an internal temperature of 60C. The flask was charged with intermediate 7 (110.0 g, 0.272 mol, AMRI lot No. DUG-AF-202Q)) and anhydrous THF (2.2 L, 20 vol). The slurry was stirred and a light green solution formed. The addition funnel was charged with 1.0 M lithium hexamethyldisilazide (299 mL, 0.286 mol, 1.05 eq.). The LiHMDS solution was added dropwise to the solution of intermediate 7 over approximately 25 minutes. A red solution formed. The solution was stirred one hour at room temperature and then DMPU (34.9 g, 0.272 mol, 1 eq) was added, and the mixture turned to a yellow slurry. The batch was cooled in an ice bath to 5.7C. R-(-)-Glycidyl butyrate (41.25 g, 0.286 mol, 1.05 eq) was then added in one portion. The mixture was stirred in the ice bath for 0.5 hour and then was warmed to room temperature and stirred overnight. The reaction formed a tan slurry at this point, and HPLC analysis after 15 hours indicated that there was approximately 87% TR-700, 1.6% intermediate 7, and approximately 7% of the butyrate ester of TR-700. A small amount of sodium methoxide in methanol (11 mL, 0.1 vol) was added, and the batch was stirred for 1 hour to remove the residual ester. The in-process HPLC analysis at this point showed there was approximately 90.7% TR-700 and 0.2% of the butyrate ester. The reaction was quenched by the addition of 10% w/w ammonium chloride solution (1.1 L, 10 vol). A modest exothermic event from 22C to 25C was observed upon addition of the ammonium chloride solution. The two-phase mixture was distilled to a pot temperature of 700C (atmospheric pressure) to remove approximately 2.2 L of the THF. This formed a thick slurry which is diluted with water (550 mL, 5 volumes). The slurry was cooled to room temperature (23.6C) and was filtered. The filter cake was washed with water (1.1 L, 10 vol) and methanol (550 mL, 5 vol) to give TR-700 as a white solid. The wet cake was dried overnight in a vacuum oven at 500C to give 89.7 g of TR-700 (89% yield) that was 97.8% (AUC) by HPLC analysis. The TR-700 was further purified by reslurrying in 2.7 L (30 vol) of 4: 1 methanol/water at 700C, cooling to 230C, filtering and washing with methanol (180 ml). This removed some of the over-alkylated product that is observed. The purified TR- 700 was recovered in 96% yield (85% overall yield), and the purity was improved to 98.4% (AUC) by HPLC analysis. The palladium content was 10 ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1220910-89-3, Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; TRIUS THERAPEUTICS; COSTELLO, Carrie, A.; SIMSON, Jaqueline, A.; DUGUID, Robert, J.; PHILLIPSON, Douglas; WO2010/42887; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 103058-87-3, 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. 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, molecular formula is C7H6BrNO2, 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) 5-Bromo-2-methoxv-3- (4-methoxv-but-1 (E, Z)-envl)-pyridine; 2.45 mi of a 1 M 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 ml 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 hydrogen- carbonate 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 (Si02 60F) and identified based on its Rf value.

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 103058-87-3, 5-Bromo-2-methoxynicotinaldehyde.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90305; (2005); A1;,
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. 84199-61-1, name is 3-Acetyl-2-bromopyridine. A new synthetic method of this compound is introduced below., Quality Control of 3-Acetyl-2-bromopyridine

Step 1: To a solution of 4-chloro-2-nitroaniline (474mg, 2.75mmol), 1-(2-bromopyridin-3- yl)ethanone (500mg, 2.500mmol), Pd2(dba)2 (114mg, 0.125mmol), (9,9-dimethyl-9H-xanthene- 4,5-diyl)bis(diphenylphosphine) (Xantphos) (217mg, 0.375mmol), cesium carbonate (3.2g, 10.00mmol) in 1,4-dioxane (10mL) was degassed by bubbling nitrogen through the reaction mixture. The mixture was heated to reflux and left overnight and then cooled to RT. Boc2O (818mg, 3.75mmol) and DMAP (458mg, 3.75mmol) were added and stirred for 3-4 h. When the reaction was complete it was diluted with dichloromethane and filtered through a pad of celite washed three times with dichloromethane, and the solvent removed to afford crude tert-butyl (3- acetylpyridin-2-yl)(4-chloro-2-nitrophenyl)carbamate as a solid which was used in the next step without further purification. MS: 392 (M+1).

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, 84199-61-1, 3-Acetyl-2-bromopyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WITTER, David, J.; BIFTU, Tesfaye; BIJU, Purakkattle; BOGEN, Stephane, L.; HONG, Qingmei; HUANG, Chunhui; HUANG, Xianhai; LI, Bing; PARK, Min, K.; SLOMAN, David, L.; (104 pag.)WO2017/74914; (2017); 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.98139-15-2, name is 4-Aminopicolinonitrile, molecular formula is C6H5N3, molecular weight is 119.124, as common compound, the synthetic route is as follows.COA of Formula: C6H5N3

To ethyl 3-fluoro-l -methyl -4-[[(lR)-2,2,2-trifluoro-l-methyl-ethyl]sulfamoyl]pyrrole-2- carboxylate (128 mg, 0.37 mmol)and 4-aminopyridine-2-carbonitrile (57.2 mg, 0.48 mmol) dissolved in dry THF (20 mL) at 0C under nitrogen atmosphere, lithium (0240) bis(trimethylsilyl)amide in toluene (1.5 mL, 1 M, 1.478 mmol) was added. The mixture was stirred 1 hour at 0C and further overnight at room temperature. The reaction mixture was quenched with NH4C1 solution (30 mL) and extracted with EtOAc (50 mL), diluted with brine (50 mL) and extracted again with EtOAc (50 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated. The residue (dissolved in 1 mL DMF) was purified by column chromatography on silica gel using a 120g Reveleris cartridge with a gradient from 10 till 100% EtOAc in heptane. The product fractions were concentrated and the solid residue was crystallised from warm methanol (20 mL) upon addition of water. The light yellow crystals were filtered off and dried in vacuo at 50C overnight, resulting in compound 18 (47 mg). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.18 (d, J=6.8 Hz, 3 H), 3.82 (s, 3 H), 3.93 – 4.04 (m, 1 H), 7.62 (d, J=4.4 Hz, 1 H), 7.91 (dd, J=5.7, 2.2 Hz, 1 H), 8.21 (d, J=1.8 Hz, 1 H), 8.60 – 8.69 (m, 2 H), 10.72 (s, 1 H). Method D: Rt: 1.70 min. m/z: 418.0 (M-H)~ Exact mass: 419.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75279-39-9, 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 75279-39-9, name is N-(4-Aminopyridin-2-yl)acetamide. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of ethyl 2,4-dichloropyrrolo[2, 1 -J] [1 ,2,4]triazine-5-carboxylate (2 g, 7.69 mmol) N-(4-aminopyridin-2-yl)acetamide (1.744 g, 11.54 mmol)in 2-propanol (20 mL) DIPEA (4.03 mL, 23.07 mmol) was added. The reaction mixture was stirred at 50 C for 3 h. The reaction mixture was cooled to room temperature and filtered. The residue was taken in 5% methanol in DCM washed with aqueous sodium bicarbonate.The organic phase was concentrated to get ethyl 4-((2-acetamidopyridin-4-yl)amino)-2-chloropyrrolo[2, 1 -J] [1 ,2,4]triazine-5-carboxylate (1.4 g, 3.74 mmol, 48.6 %yield) as a white solid. LCMS m/z 375.1 (M+H); rt 1.25 mm; Conditions B

According to the analysis of related databases, 75279-39-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; RAHAMAN, Hasibur; WARRIER, Jayakumar Sankara; SESHADRI, Balaji; (411 pag.)WO2017/15425; (2017); 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.87674-15-5, name is 1-(3-Fluoropyridin-4-yl)ethanol, molecular formula is C7H8FNO, molecular weight is 141.14, as common compound, the synthetic route is as follows.COA of Formula: C7H8FNO

A mixture of 1- (3-FLUOROPYRIDIN-4-YL) ETHANOL (10 g, 70.3 MMOL) and commercial activated Mn02 (8 G, 92.1 MMOL) in toluene (100 mL) were REFLUXED until disappearance of starting material. After cooling the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3-FLUORO-4-ACETYL pyridine (6.9 g, 70%) that was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87674-15-5, 1-(3-Fluoropyridin-4-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA ITALIA S.P.A.; WO2005/13986; (2005); 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. 29681-42-3, name is Methyl 4-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 29681-42-3

Example 17, Compound 17; (E)-(1 S,14R,15R,18S,21 S)-21 -(3-Hydroxy-benzyl)-18-isopropyl-14-methoxy-15-methyl-3-oxa-6,17,20,23,27-pentaaza-tricyclo[21.3.1.1 *5,9*]octacosa- 5 7,9(28),10-tetraene-2,16,19,22-tetraone; Com ound 17a: (4-Bromo-pyridin-2-yl)-methanol.; Sodium borohydride (763 mg, 20.17 mmol) was added portionwise to a solution of 4- bromo-pyridine-2-carboxylic acid methyl ester (1 .98 g, 9.166 mmol) in ethanol (50 mL) under nitrogen and the reaction mixture was stirred at room temperature for 18 hours. The reaction was quenched by the addition of acetone (10 mL) and the reaction was stirred for 15 minutes. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organics were collected, dried over anhydrous sodium sulfate and the solvent evaporated to afford the title compound (1 .61 g, 94%) as a yellow oil. H NMR (300 MHz, CDCI3) 3.4-3.5 {br s, 1 H), 4.80 (s, 2H), 7.40 (dd, J = 5.4, 1 .8 Hz, 1 H), 7.50 (br m, 1 H), 8.39 (d, J = 5.4 Hz, 1 H). LCMS (m/z) 188/200 [M+H], Tr = 1 .55 min.

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, 29681-42-3, Methyl 4-bromopicolinate.

Reference:
Patent; GILEAD SCIENCES, INC.; SELCIA LIMITED; APPLEBY, Todd; FLIRI, Hans, G.; KEATS, Andrew, J.; LAZARIDES, Linos; MACKMAN, Richard, L.; PETTIT, Simon, N.; POULLENNEC, Karine, G.; SANVOISIN, Jonathan; STEADMAN, Victoria, A.; WATT, Gregory, M.; WO2012/78915; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem