Category: pyridine-derivatives

Related Products of 127446-34-8, 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 127446-34-8, name is N-(6-Chloro-3-formylpyridin-2-yl)pivalamide. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-Benzyloxy-butan-l-ol (12) (8.43 mL, 48 mmol) in DMF (50 mL) was treated with NaH (1.52 g, 60 mmol) at O0C under nitrogen. The mixture was stirred at this temperature for 15 min, and then treated with N-(6-Chloro-3-formyl-pyridin-2-yl)-2,2- dimethyl-propionamide (11), (Journal of Organic Chemistry, 55(15), 4744-50; 1990, 5.76g, 24 mmol) in portions. After the addition was over, the mixture was left stirring for another 1 h. Aqueous NH4Cl was added to quench the reaction. The mixture was taken up into EtOAc and washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (13) (6.15g) 1H-NMR (400 MHz, CDCl3): 11.50 (s, IH), 9.75 (s, IH), 7.80 (d, IH), 7.40 – 7.20 (m, 5H), 6.45 (d, IH), 4.50 (m, 4H), 3.50 (t, 2H), 2.00 – 1.70 (m, 4H), 1.40 (s, 9H).

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 127446-34-8, N-(6-Chloro-3-formylpyridin-2-yl)pivalamide.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/103559; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10177-32-9, 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 10177-32-9 as follows.

MeI (0.2 mL, 3.00 mmol, 0.25 equiv) was added to a solution of methyl ester 14 (2 g, 12 mmol) in MeCN (16 mL), and the mixture was heated at 120 C under microwave conditions for 1 h. The solvent wasthen removed, and the oily residue was taken up in EtOAc, treated with charcoal, filtered, and re-concentrated to give 4-pyridinone 16 as a viscous oil that solidified to a near colourless solid on standing (2g, 95%). IR (ATR): 1645, 1717, 2950, 3013, 3053, 3094 cm-1. 1H NMR (CDCl3): delta = 8.12 (s, 1 H), 7.21-7.24 (dd, 3J = 7.7 Hz, 4J = 2.5 Hz,1 H), 6.44 (d, 3J = 7.5 Hz, 1 H), 3.83 (s, 3 H), 3.69 (s, 3 H). 13C NMR (CDCl3): delta = 174.8, 165.3, 146.6, 139.8, 122.7, 118.1, 51.9,44.9. HRMS (HESI): m/z [M + H]+ calcd for C8H9NO3: 168.0655; found:168.0657.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10177-32-9, its application will become more common.

Reference:
Article; Koperniku, Ana; Zamiri, Maryam; Grierson, David S.; Synthesis; vol. 51; 8; (2019); p. 1779 – 1790;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1279815-46-1 ,Some common heterocyclic compound, 1279815-46-1, molecular formula is C9H7BrN2, 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.

To a chilled (-78C) solution of l-(2-bromopyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.2 mmol) in toluene (30 mL) is added a 1 M solution of diisobutylaluminum hydride (DIBAH) (10.4 mL) in toluene. The mixture stirred at -78C for 1 hour and is then warmed to room temperature. After 1 hour, EtOAc (30 mL) is added, followed by 1 M aqueous solution of H2S04 (30 mL). The organic phase is separated and the aqueous layer is extracted with EtOAc (3 x 50 mL). The combined organic layers are dried over MgS04, filtered and concentrated to afford crude l-(2-bromopyridin-4-yl)- cyclopropanecarboxaldehyde which is used without purification. MS mJz 226.5, 228.5

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. 1279815-46-1, 1-(2-Bromopyridin-4-yl)cyclopropanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; WO2011/56440; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 26163-03-1, 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. 26163-03-1, name is 3-Bromo-5-chloropyridin-2-amine, molecular formula is C5H4BrClN2, 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.

Example 39 2′-amino-6-(6-chloroimidazo[ 1 ,2-a]pyridin-8-yl)- 1 ‘,2,2-trimethylspiro[chroman-4,4′- imidazol]-5′(l’H)-oneStep A: 3-Bromo-5-chloro-2-pyridinamine (487 mg, 2.35 mmol) was diluted with ethanol (4 mL), followed by the addition of 2-chloroacetaldehyde (614 , 4.69 mmol). The reaction was heated at reflux for 3 hours. The reaction was cooled and loaded onto silica gel eluting with 10-50% ethyl acetate/hexanes to yield 8-bromo-6-chloroimidazo[l,2-a]pyridine (300 mg, 1.30 mmol, 55.2% yield).Step B: 2’-Amino-r,2,2-trimethyl-6-(4,4,5,5-tetramethyl

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 26163-03-1, 3-Bromo-5-chloropyridin-2-amine.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 106961-33-5, N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine, 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: 106961-33-5, blongs to pyridine-derivatives compound. Recommanded Product: 106961-33-5

Step (ii): Preparation of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a|pyridine-3- acetonitrile (10)Dissolved the 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-N,N- dimethylmethylamine (8) ( (230 grams, 0.82 mmol) (obtained from step (i)) in dichloromethane (600 mL) under stirring. Cooled the above solution to 0 – 5 0C, add ethylchloroformate (98.4 grams, 0.90 mmol) slowly over a period of 30 minutes. Stirred the above reaction mass for a period of 45 minutes at the same temperature, distilled off the solvent under reduced pressure, which produced 332 grams crude carbamate salt of dimethylaminomethyl imidazopyridine (2) as yellow colored solid. Dissolved the obtained solid immediately in water (690 mL), basify the solution to pH 7.5-8.0 using 10% sodium hydroxide solution. Added sodium cyanide (48.4 grams, 0.99 mmol) to the above reaction mass and stirred at 50 – 55 0C for a period of 3 hours. Cooled the above reaction mass to room temperature, extracted the solution with chloroform (300 mL, 2×200 mL). Combined organic layers and washed with water (500 mL) and brine (400 mL). Dried with anhydrous sodium sulfate, filtered and concentrated the solution until the volume reaches to 250 mL. Add methanol (1000 mL), stirred for the period of 30 minutes. Filtered the formed off white solid from the solution and dried in the oven until constant weight reached. Dry weight of obtained 6- methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-acetonitrile(10) is 165.0 grams. Yield: 76% Purity: 96%Melting Range: 176.9 – 178.00C;IR spectra (cm”1): 2921, 2895, 2249, 1500, 1386, 1343, 824, 799;1H NMR (400 MHz, CDCl3): delta 2.42(s, 6H), 4.13 (s, 2H), 7.16 (dd, J= 9.1 Hz, J= 1.5 Hz, IH), 7.31 (d, J= 7.9 Hz, 2H), 7.58 (d, J= 8.0 Hz, 2H), 7.60 (d, J= 9.6 Hz, IH), 7.80(s, IH);Mass (m/z): 262.5 (M+H)+; Example 2:Preparation of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3- acetic acid (12)Dissolved the 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine (9) (100 grams, 0.45 mmol) in acetic acid (500 mL) under stirring. Cooled the reaction mass to 5 – 10 0C, added 40% aqueous solution of dimethylamine (76 grams) slowly, followed by addition of paraformaldehyde (17.7 grams). Stirred the reaction mass at 50 – 55 0C for the period of 3 hours and removed acetic acid under reduced pressure. Added water (1000 mL), basify the solution (pH 8.0) by adding 30% sodium hydroxide solution. Extracted the solution with dichloromethane (3×300 mL), washed the organic layer with water (500 mL) and brine solution (500 mL). Dry with anhydrous sodium sulfate, filtered and distilled the solvent until the volume reaches to around 300 mL. This solution contains 6-methyl-2-(4-methylphenyl)imidazo[l ,2-a]pyridine-3-N,N- dimethylmethylamine (10), 89% purity by HPLC, and used further as it is. Cooled the above organic solution to 0 – 5 0C, added ethylchloroformate (58.3 grams, 0.54 mmol) slowly over a period of 30 minutes. Stirred the reaction mass for one hour at the same temperature, distilled off the solvent under reduced pressure to obtain carbamate salt as bright yellow colored solid (2). This solid was dissolved in water (300 mL), basified the solution to pH 7.5 – 8.0 using 10% sodium hydroxide solution. Added sodium cyanide (26.5 grams, 0.54 mmol) and stirred the reaction mass at 50 – 55 0C for a period of 3 hours. Cooled the reaction mass to room temperature and filtered the yellow solid and washed with water (500 mL). This crude solid contains 6- methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-acetonitrile (10), 82% purity by HPLC, and used for hydrolysis without any further purification. The above crude solid was dissolved in 50% sulfuric acid (624 mL), refluxed the reaction mass at 110 0C for 4 hours. Cooled the reaction mass to room temperature and added to a flask contain of ice cold water (2.5 L). Basified the white ppt solution by adding sodium hydroxide flakes portion wise until pH 9.0. Extracted the solution with dichloromethane (2 x 300 mL) and discarded. Added carbon (5.0 grams), stirred for 30 minutes and filtered through a pad of celite. Acidified the solution pH 5.5 by adding glacial acetic acid and obtained white solid filtered. Filtered cake was washed with water (500 mL) and dried in the airflow oven at 60 – 65 0C until constant weight reached. 78.0 grams of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3- aceticacid (12) obtained as off-white solid. Yield: 62.0% Purity: 99.5 %Melting Range: 234.0 – 235.20C; IR spectra (cm 1): 3427, 2919, 1701, 1508, 1183, 827, 805; 1H NMR (400 MHz, DMSO-c4): delta 2.31 (s, 3H), 2.34 (s, 3H), 4.08 (s, 2H), 7.17 (dd, J=9.1 Hz, J= 1.5 Hz, IH), 7.28 (d, J= 8.0 Hz, 2H), 7.51 (d, J= 9.1 Hz, IH), 7.61 (d, J= 8.0Hz, 2H), 8.22 (s, lH);Mass (m/z): 281.2 (M+H)+

The synthetic route of 106961-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; WO2009/7995; (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. 944900-06-5, name is 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, the common compound, a new synthetic route is introduced below. Product Details of 944900-06-5

2-Chloro-6-(trifluoromethyl)nicotinaldehyde (176 mg, 0.840 mmol), cyclopropylboronic acid (152 mg, 1.76 mmol), sodium carbonate (267 mg, 2.52 mmol) and tetrakis(triphenylphosphine)palladium (0) (48.5 mg, 0.0420 mmol) were combined, diluted with toluene (2 mL) and water (200 muL). The reaction vial was purged with argon, heated to 900C and stirred for 24 hours. The reaction was allowed to cool, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 2-cyclopropyl-6- (trifluoromethyl)nicotinaldehyde (130 mg, 0.604 mmol, 71.9 % yield).

The synthetic route of 944900-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1142363-52-7, name is JNJ-40346527. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1142363-52-7

Example 23 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide hydrochloride salt A solution of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (49.2 mg, 0.107 mmol, as prepared in Example 15, step (h)) in EtOH (2 mL) was treated with HCl (26.6 muL, 0. 107 mmol, 4 M in dioxane) at room temperature for 1.5 h. The solvents were evaporated in vacuo, and the residue was dried under high vacuum overnight. The solid was dissolved in a minimum amount of EtOH (900 muL) with sonication and heating. While warm, the solution was slowly treated with hexanes (3 mL) to the cloud point. The mixture was heated again until clear, the sides of the vial were scratched, and the mixture was allowed to cool. The solid was filtered and air-dried to afford the title compound (20mg, 38%) as white crystals. 1H-NMR (CD3OD; 400 MHz): delta 9.17 (d, 1H, J=8.4 Hz), 8.10 (s, 1H), 7.95 (d, 1H, J=8.4 Hz), 6.38-6.32 (m, 1H), 3.76-3.65 (m, 1H), 2.54-2.46 (m, 2H), 2.25-2.19 (m, 2H), 1.98-1.91 (m, 2H), 1.76-1.65 (m, 4H), 1.43 (s, 6H), 1.30 (s, 6H), 1.15 (s, 6H). Mass spectrum (APCI, m/z): Calcd. for C27H35N5O2, 462.3 (M+H), found 462.3.

With the rapid development of chemical substances, we look forward to future research findings about 1142363-52-7.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (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. 20511-15-3, name is 3-Amino-4-chloropyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H5ClN2

[Example 719] Compound q1 4-Chloropyridine-3-carbonitrile [1519] aqueous tetrafluoroboric acid solution (10 ml) was added to a solution of 4-chloropyridin-3-amine (1.29 g, 10.0 mmol) in ethanol (10 ml) at 0C. An aqueous solution (10 ml) of sodium nitrite (725 mg, 10.5 mmol) was added to the resultant mixed solution at the same temperature, and it was stirred at the same temperature for 30 minutes. The precipitate was collected by filtration and washed with ethanol, and the resultant brown solid (1.94 g) was then dissolved in acetonitrile (10 ml). A mixed solution of sodium cyanide (980 mg, 20.0 mmol) and copper(I) cyanide (896 mg, 10.0 mmol) in water (10 ml) and acetonitrile (1 ml) was added to the resultant solution at 0C, and it was stirred while gradually warming to room temperature for 10 hours. The reaction mixture was cooled to 0C, after which a saturated aqueous solution of sodium bicarbonate was added, and it was stirred for five minutes. The resultant solution was extracted with ethyl acetate, and the organic layer was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (605 mg, 44%) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) delta: 8.87 (1H, s), 8.72 (1H, d, J = 3.9 Hz), 7.51 (1H, d, J = 3.9 Hz).

The synthetic route of 20511-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; MURATA, Takeshi; NIIZUMA, Satoshi; HARA, Sousuke; KAWADA, Hatsuo; HADA, Kihito; SHIMADA, Hideaki; TANAKA, Hiroshi; NAKANISHI, Yoshito; EP2842939; (2015); 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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid. A new synthetic method of this compound is introduced below., Quality Control of 2-Fluoro-4-iodonicotinic acid

To a solution of the product from step 2 (23.5 g, 88 mrnoi) in methanol (300 mL) was added dropwise TMSCHN2 (220 mL, 440 minol) at 05C under N2 . After addition was complete, the mixture was stirred at RT for 16 hrs, water was added and the mixture extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. The crude product was purified bychromatography on silica (10% EtOAc in petroleum ether) to give the title compound as an oil. LRMS m/z M+H) 282.1 found, 282.1 required.

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, 884494-51-3, 2-Fluoro-4-iodonicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below.

To a solution of ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 5.51 mmol) in dimethylformamide was added slowly sodium hydride (242 mg, 6.06 mmol) at 0 C, followed by iodomethane (821 mg, 5.79 mmol). The mixture was stirred at same degree for 1 hour, and then quenched with water. The resulting mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulphate and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)propanoate (790 mg, 67 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,197376-47-9, Ethyl 6-Chloropyridine-3-acetate, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; WO2013/13815; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem