Category: pyridine-derivatives

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. 16744-81-3, name is 4-Methoxypicolinaldehyde, molecular formula is C7H7NO2, 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. category: pyridine-derivatives

2. (R SS2-[4-(4-METHOXYPYRIDIN-2-YL) BUT-2-YL]-3H-I MIDAZO [4. S-B] PYRID INE; A solution of 7.2 g of tributyl-{1-(3H-imidazo [4,5-b] PYRIDIN-2-YL)-PROPYL}-PHOSPHONIUM chloride (compound A2) in tetrahydrofurane is added to a suspension of 720 mg of sodium hydride (60percent strength suspension in paraffin) in 180 ml of tetrahydrofurane. After 15 min stirring, a solution of 0.500 g of 4-methoxypyridine- 2-carbaldehyde (Ashimori et AL., Chem. Pharm. Bull. 38,2446-2458 (1990) ) in tetrahydrofurane is added dropwise and the reaction mixture is heated at 80°C for 6 h. The mixture is then evaporated to dryness and the resulting residue chomatographed on silica gel using DICHLOROMETHANE/METHANOL 20: 1 to give 3.58 g of a colorless, amorpheous solid, which is dissolved as obtained in 200 ml of methanol. 2.9 ml of trifluoracetic acid and 788 mg of palladium on active carbon (10percent Pd) are added and the suspension is stirred at room temperature for 2.5 d under hydrogen atmosphere. Then the catalyst is filtered off and the reaction mixture is concentrated to dryness. After chromatographical purification of the residue on silica gel (DICHOROMETHANE/METHANOL 10: 1 to 5: 1) and evaporation of the eluents, 1.4 g of the title compound are obtained as an oil. MS: 283.1 (MH+). TLC: Rf = 0.48 (DICHLOROMETHANE/METHANOL 10: 1).

With the rapid development of chemical substances, we look forward to future research findings about 16744-81-3.

Reference:
Patent; ALTANA PHARMA AG; WO2005/30768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003711-43-0, 2-Bromo-5-hydroxy-3-methylpyridine, 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: C6H6BrNO, blongs to pyridine-derivatives compound. Formula: C6H6BrNO

To a mixture of 2-bromo-5-hydroxy-3-picoline (2.18 g, 11.59 mmol), TEA (19.39 mL, 139 mmol), and MeOH (30 mL, 740 mmol) in a 250 mL pressure tube was added 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (335 mg, 0.58 mmol) and palladium (II) acetate (65 mg, 0.29 mmol). The mixture was evacuated-purged with CO gas (balloon) 3- times. The valves were closed and the mixture was heated at 70 C for 24 h. The mixture was filtered through a pad of Celite filter aid. The Celite filter aid was washed with MeOH. The filtrate was concentrated in vacuo and dissolved in DCM (50 mL). The organic solution was washed with saturated NaHCO3 (30 mL). The aqueous layer was saturated with NaCl and extracted with 2% IPA in CHCl3 (3 x 20 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude was purified by silica gel chromatography using 1 -5% MeOH in DCM to give the product as an off- white solid (1.65 g, 85%). LCMS (ESI, pos.) 168.0 (M+1 )+. 1H NMR (400 MHz, DMSO-d6) delta 10.57 (br. s., 1 H), 8.02 (d, J=2.54 Hz, 1 H), 7.08 (d, J=2.15 Hz, 1 H), 3.79 (s, 3H), 2.44 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1003711-43-0, 2-Bromo-5-hydroxy-3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); 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. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 7477-10-3

Synthesis (compoundof 6- (4-Ethoxyphenylamino) -5-nitronicotinic acid 22-2)[0000150] To a solution of 6-chloro-5-nitronicotinic acid (22-1) (10 g, 49 mmol, 1.0 equiv) in acetonitrile (150 mL) was added triethylamine (15.1 mL, 109 mmol, 2.2 equiv) and 4- ethoxyaniline (6.7 mL, 52 mmol, 1.05 equiv) . The mixture was heated refluxed for 18 hours and concentrated under reduced pressure. The residue was suspended in water (100 mL) and the pH adjusted to 4 with 6N hydrochloric acid. The aqueous phase was extracted with a 2:1 mixture of ethyl acetate and tetrahydrofuran (4 x 100 mL) . The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure to give crude compound 22-2 (14 g, 96% yield) as a black solid.

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, 7477-10-3, 6-Chloro-5-nitronicotinic acid.

Reference:
Patent; SIGA TECHNOLOGIES, INC.; DAI, Dongcheng; BURGESON, James, R.; AMBERG, Sean, M.; HRUBY, Dennis, E.; WO2013/123215; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 54864-83-4 ,Some common heterocyclic compound, 54864-83-4, molecular formula is C8H9ClN2O, 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.

6-((3S)-3-{[(4-Hydroxy-l-adamantyl)carbonyl]amino}piperidin-l-yl)-N,N-dimethylnicotinamideA mixture of 4-hydroxy-N-[(3S)-piperidin-3-yl]adamantane-l-carboxamide (13.9 mg, 0.0000500 mol, prepared by using a procedure that was analogous to that described for the synthesis of example 141, steps 1-3), 6-chloro-N,N-dimethylnicotinamide (13.8 mg, 0.0000750 mol) andN,N-diisopropylethylamine (19.4 mg, 0.000150 mol) in N,N-dimethylformamide (0.500 mL, 0.00646 mol) was irradiated under microwave at 120 C for 10 min. The mixture was adjusted with TFA to pH =2.0 and was diluted with methanol (0.8 mL). The resulting solution was purified by prep.-HPLC to give the desired product. LCMS: (M + H)+ = 427.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54864-83-4, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; WO2006/20598; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75806-86-9, 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 75806-86-9 as follows.

Example 3: General procedure A: Synthesis of 5-chloro-3-nitro-2-aryloxy- pyridines and 5-chloro-3-nitro-2-arylsulfanyl-pyridines; [00383] A mixture of the appropriate hydroxyaryl or thioaryl (1.3 equiv), 2- bromo-5-chloro-3-nitro-pyridine (1 equiv) and K2CO3 (1.5 equiv) in DMF was heated at 80 C overnight. The resulting mixture was cooled to room temperature, and diluted with water and CH2CI2. The biphasic mixture was separated and the aqueous portion was extracted with CH2CI2. The combined extracts were washed with saturated aqueous NaHCO3, brine and dried (Na2SO4). It was then filtered and filtrate was concentrated under reduced EPO pressure and the product was purified by flash column chromatography on silica gel to provide desired product.; Example 4: 5-Chloro-3-nitro-2-phenoxy-pyridine; [00384] This compound was prepared according to the general procedure described above using 2-bromo-5-chloro-3-nitro-pyridine (500 mg, 2.11 mmol), phenol (258 mg, 2.75 mmol), K2CO3 (437 mg, 3.16 mmol) and DMF (2 mL). MS m/z : 250.4 (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,75806-86-9, its application will become more common.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 847729-27-5 ,Some common heterocyclic compound, 847729-27-5, molecular formula is C7H5ClFNO2, 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 methyl 2-chloro-5-fluoronicotinate (step 1,1.5 g, 7.91 mmol), tetrakis (triphenylphoshine)palladium (914 mg, 0.79 mmol), methyboronic acid (521 mg, 8.70 mmol) and potassium carbonate (3.28 g, 23.7 mmol) in 1,4- dioxane (20 ml) was heated at 110 C for 20 h under nitrogen atmosphere. The reaction mixture was filtered through a pad of celite (Celite(trademark) (diatomaceous earth) ) and the filtrate was concentrated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (20/(at) to 4/1 ) to afford 936 mg (64%) of the title compound: ¹H-NMR (CDCl3) 8 8.49 (1H, d, J = 3.0 Hz), 7.93 (1H, dd, J = 3.0, 8.7 Hz), 3.94

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. 847729-27-5, Methyl 2-chloro-5-fluoronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/102389; (2005); A2;,
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 942060-13-1, name is 3-(Bromomethyl)-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 942060-13-1

To a 100-mL round-bottomed flask were added 3-(bromomethyl)-2- methoxypyridine (1.10 g, 5.44 mmol), ethyl N-(diphenylmethylene) glycinate (1.46 g, 5.44 mmol, Acros, New Jersey) and 5N sodium hydroxide (5.44 mL, 27.2 mmol) in tetrahydrofuran (30 mL). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2 x 50 mL). The organic extract was washed with saturated NaCl (20 mL) and dried over Na2S04. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give ethyl N-(diphenylmethylidene)-3-(2-methoxy-3- pyridinyl)alaninate (1.52 g) as viscous oil.

With the rapid development of chemical substances, we look forward to future research findings about 942060-13-1.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael David; BO, Yunxin; BRYAN, Marian C.; CROGHAN, Michael; FOTSCH, Christopher Harold; HALE, Clarence Henderson; KUNZ, Roxanne Kay; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis Dale; POON, Steve Fong; STEC, Markian Myroslaw; ST. JEAN, David, Joseph, Jr.; TAMAYO, Nuria A.; TEGLEY, Christopher Michael; YANG, Kevin Chao; WO2012/27261; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 76015-11-7 ,Some common heterocyclic compound, 76015-11-7, molecular formula is C7H9NO2, 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.

Reference Example 2 3-Methoxy-2-methyl-4(1H)-pyridone (5.6 g) was suspended in phosphorus oxychloride (50 ml), refluxed for 10 hours, and concentrated. To the resultant residue was added toluene and the residual phosphorus oxychloride was evaporated under reduced pressure. To the resultant oily substance were added chloroform and water and the chloroform layer was separated. The aqueous layer was made alkaline with potassium carbonate and extracted with chloroform. The chloroform solutions thus obtained were combined, washed with water, dried, and evaporated. The residue was purified by column chromatography on silica gel, to give 4-chloro-3-methoxy-2-methylpyridine (4.8 g) as a light brown oil. NMR(CDCl3)delta:2.53 (3H,s), 3.84(3H,s), 7.14(1H,d,J=6Hz), 8.12 (1H,d,J=6Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76015-11-7, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP208452; (1991); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 436799-32-5, 5-Bromo-2-(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, name: 5-Bromo-2-(trifluoromethyl)pyridine, blongs to pyridine-derivatives compound. name: 5-Bromo-2-(trifluoromethyl)pyridine

In a dried 250 mL 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (16 mL, Aldrich, inhibitor free) followed by N, N-diisopropylamine (0.895 g, 8.85 mmol, Aldrich, redistilled 99.95% pure). After cooling the stirred solution to -70 0C, n-butyl lithium (3.54 mL of a 2.5M solution in hexanes, 8.85 mmol) was added dropwise, keeping the reaction temperature less than -60 0C. The resulting solution was stirred at -70 0C for a further 10 min, then warmed to -20 0C, before immediately cooling to -90 0C. A solution of 5-bromo-2-(trifluoromethyl)pyridine (2 g, 8.85 mmol) in anhydrous THF (8 mL, Aldrich, inhibitor free) was added dropwise, keeping the reaction temperature less than -85 0C. The resulting orange solution was stirred at -90 0C for 40 min.In a separate dried 250 mL 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (5 mL, Aldrich, inhibitor free) followed by methyl iodide (5 mL, 80 mmol). The solution was cooled to -90 0C. To this was added (via cannula) the solution of the pre-formed lithiated pyridine, controlling the rate so as to keep the reaction temperature of the receiving flask less than -80 0C. The resulting dark solution was stirred at -90 0C for a further 15 min (LCMS indicated reaction complete). The reaction was quenched with sat aq. NH4CI solution (50 mL), then allowed to slowly warm to room temperature. Organics were extracted with EtOAc (2 x 50 mL), then the combined organic layers washed with water (50 mL), then brine (50 mL), separated, dried over MgSO4, and then filtered. Concentration in vacuo gave 1.68 g of a brown oil which was purified via short-path vacuum distillation (45-46 0C, ca. 5 mmHg) to give 5-bromo-4-methyl-2- (trifluoromethyl)pyridine 1-2 (0.289 g, 14%) as a yellow oil (>97% pure). MS (M + H)+: 241.8, tR = 2.458 min (method 1 ); 1H NMR (CDCI3) delta 8.74 (1 H, s), 7.56 (1 H, s), 2.50 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,436799-32-5, 5-Bromo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124610; (2008); 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. 89694-10-0, name is 2-Methoxy-3-methyl-5-nitropyridine, molecular formula is C7H8N2O3, 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. Application In Synthesis of 2-Methoxy-3-methyl-5-nitropyridine

(lc) 6-Methoxy-5-methyl-3-pyridinamine [Formula 10]; 2-Methoxy-3-methyl-5-nitropyridine (1.63 g, 9.71 mmol) was dissolved in methanol (50 ml), 10% Pd- on-carbon powder (50% water content article) (800 mg) was added, and stirred under hydrogen atmosphere for 2 hours and 10 minutes. After the reaction was completed, celite filtration was carried out, the solvent was evaporated, thereby yielding the title compound (1.25 g, 0.90 mmol, 93%) as a blue oily substance. ¹H NMR(400 MHz, DMSO-d6) 8 ppm; 2.03(3H, s), 3.73(3H, s), 4.62 (2H, s), 6.83-6.86(lH, m), 7.31-7.34(lH, m),

With the rapid development of chemical substances, we look forward to future research findings about 89694-10-0.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem