Pyridine-derivatives

Electric Literature of 76006-11-6 ,Some common heterocyclic compound, 76006-11-6, molecular formula is C6H4ClN3, 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.

Trimethylaluminum (23.9 mL, 47.8 mmol, 2M sol. in toluene) was added to a vigorously stirred solution of 7-chloro-iH-pyrazolo[3,4-c]pyridine (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1.38 g, 1.19 mmol) in THF (109 mL) under argon. The reaction mixture was stirred at 65C for 16 h, cooled to RT and poured into sat. aq. NH4CI solution. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3x). The combined organic extracts were washed with brine then dried (phase separator) and concentrated to give 7-methyl-i H-pyrazolo[3,4-c]pyridine as a solid. MS (LC/MS): 134 [M+H]+, tR (HPLC conditions d): 0.25 mm.

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. 76006-11-6, 7-Chloro-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige, Liliane, Jeanne; MAIBAUM, Juergen, Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan, Andreas; VULPETTI, Anna; WO2014/2054; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 490-11-9 ,Some common heterocyclic compound, 490-11-9, molecular formula is C7H5NO4, 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 mixture of pyridine-3,4-dicarboxylic acid (10.00 g, 60.00 mmol, 1 eq) and a catalytic amount of DMAP (50 mg) in 300 mL of anhydrous MeOH was added dropwise SOCl2 (21.4 mL, 300.00 mmol, 5 eq) at 0 C. The reaction mixture was heated to reflux for 48 h, cooled to room temperature and concentrated in vacuo. The crude product was dissolved in CH2Cl2 (200 mL), and the solution was washed with saturated K2CO3 aqueous solution and water (50 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to afford the title compound as pale yellow oil (8.00 g, 68.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 196.05 (M+1).

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. 490-11-9, Pyridine-3,4-dicarboxylicacid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-78-9 , The common heterocyclic compound, 69045-78-9, name is 2-Chloro-5-(trichloromethyl)pyridine, molecular formula is C6H3Cl4N, 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.

The liquid was found to contain 17 ppm tungsten. The solid (1.4 grams) was used to catalyze the chlorination of 187.6 grams of 2-chloro-5-trichloromethylpyridine at 200 C. and ambient pressure. In 98 hours, 77.5 weight percent of 2,3-dichloro-5-trichloromethylpyridine was obtained.

The synthetic route of 69045-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4532111; (1985); 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. 1072438-54-0, name is Methyl 2-(aminomethyl)pyridine-4-carboxylate hydrochloride. A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 2-(aminomethyl)pyridine-4-carboxylate hydrochloride

Take a 25 mL round bottom flask, Weigh4-carbomethoxy-2-pyridinemethylamine hydrochloride (1 g, 4.9 mmol) and potassium carbonate (1 g, 7.2 mmol) in 10 mL EtOAc. Stir at room temperature for 15 minutes; then a solution of 3-bromopropyne (0.29 g, 2.5 mmol) in 25 mL of acetonitrile was added dropwise to the mixture with a constant pressure dropping funnel. Stirring was continued at room temperature overnight (new points were generated by TLC detection).After the reaction is completed, the solvent is evaporated under reduced pressure. Add 50 mL of water to it, Extract three times with 35 mL of ethyl acetate each time. The organic phases were combined and washed with saturated brine. Dry with anhydrous sodium sulfate, After filtration, the mixture was steamed under reduced pressure. The column was wet-packed and eluted with ethyl acetate: petroleum ether: triethylamine = 25:74:1 to ethyl acetate: petroleum ether: triethylamine = 49:50:1.Yellow solid, yield 21%.

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, 1072438-54-0, Methyl 2-(aminomethyl)pyridine-4-carboxylate hydrochloride.

Reference:
Patent; Shandong University; Jia Jihui; Zhan Peng; Liu Xinyong; Chen Chunyan; Jia Xiaxia; Zhang Shuo; Yu Ji; Wang Xueshun; (9 pag.)CN109369620; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 38186-82-2, 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. 38186-82-2, name is 6-Chloro-5-methylpyridin-3-amine. A new synthetic method of this compound is introduced below.

2-Chloro-3-methyl-5-nitro-pyridine (2g, 11.6 mmol) and SnCl2No. (H2O)2 34.8 mmol) are refluxed in MeOH overnight. After cooled down, the mixture is diluted with ethyl acetate, washed with water, brine, dried over MgS04, concentrated and purified by column chromatography to afford 6-chloro-5-methyl-pyridin-3-ylamine (1.7g). To the solution of 6-chloro-5-methyl-pyridin-3-ylamine (1.7g, 11.6 mmol) in IN HCl is added the solution ofNaNOz (960mg, 13.92mmol) in water (10ml) slowly at 0 C. After the addition, the solution is stirred for 20min and then heated to 90 C for 30min. The solution is cooled down, quenched with K2C03, extracted with ether, dried over MgS04, and purified by column chromatography to afford the titled compound (560mg) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38186-82-2, 6-Chloro-5-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/123668; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56673-34-8, 3-Bromo-6-mercaptopyridine, 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, SDS of cas: 56673-34-8, blongs to pyridine-derivatives compound. SDS of cas: 56673-34-8

2.0 g of 5-Bromo-pyridine-2-thiol (compound C1 ) are dissolved in 40 ml of carbon tetrachloride and 8 ml of water. Subsequently, the suspension is cooled in an ice bath and chlorine gas is passed into the reaction mixture for 20 min (flow: 35 ml/min). Thereafter, nitrogen is passed into the yellow solution to remove excess chlorine. Subsequently, the mixture is diluted with 150 ml of dichloromethane and extracted with 50 ml of brine. The organic layer is separated, dried using Na2SO4, filtered with suction, and evaporated to dryness to afford 2.70 g of the title compound as light yellow needles. M. p. 8O0C. GC-MS: 254.8/256.8/258.8 (77:100:25; M+). TLC: Rf = 0.84 (dichloromethane/ethanol 20:1 parts by volume).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56673-34-8, 3-Bromo-6-mercaptopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ALTANA PHARMA AG; WO2007/39580; (2007); 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. 56673-34-8, name is 3-Bromo-6-mercaptopyridine, molecular formula is C5H4BrNS, 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. Formula: C5H4BrNS

A suspension of 5-bromo-pyridine-2-thiol (which may be prepared as described for Intermediate 1.05; 2 g, 10.5 mmol) in carbon tetrachloride (40 mL) and water (8 mL) was cooled to 0 C. using an ice-bath. Chlorine gas was bubbled through the reaction mixture for 20 min and then CH2Cl2 (100 mL) was added. The mixture was washed with brine. The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to give 5-bromo-pyridine-2-sulfonyl chloride (1.92 g, 71%) as a light yellow solid which was used directly in the next step without further purification. NMR (400 MHz, DMSO-d6) delta: 8.63 (d, J=1.5 Hz, 3H), 8.07 (dd, J=8.3, 2.2 Hz, 3H), 7.68 (d, J=8.3 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 56673-34-8.

Reference:
Patent; Firooznia, Fariborz; Gillespie, Paul; Lin, Tai-An; So, Sung-Sau; US2012/309796; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 62002-31-7, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, 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, Safety of 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, blongs to pyridine-derivatives compound. Safety of 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride

At 0 C., EDC (0.45 g, 2.4 mmol) was added to a solution of 1-hydroxy-7-azabenzotriazole (0.32 g, 2.4 mmol) and 2-norbornaneacetic acid (0.338 mL, 2.4 mmol) in dichloromethane (30 mL). The reaction mixture was stirred for 20 min at 0 C. 4,5,6,7-Tetrahydroimidazo[4,5-c]pyridine dihycrochloride (0.50 g, 2.3 mmol) was added. Ethyldiisopropylamine (0.40 mL, 2.3 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. It was diluted with ethyl acetate (100 mL) and washed with a saturated aqueous solution of sodium hydrogencarbonate (100 mL). The aqueous solution was extracted with ethyl acetate (2*60 mL). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 120 mg of the title compound. 1H NMR (CDCl3, 2 rotamers): delta 1.00-2.50 (m, 13H); 2.65 and 2.75 (both t, together 2H); 3.75 and 3.90 (both t, together 2H); 4.55 and 4.65 (both s, together 2H); 7.53 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62002-31-7, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22620-32-2, 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. 22620-32-2, name is (5-Fluoropyridin-3-yl)methanol. A new synthetic method of this compound is introduced below.

To a solution of (5-fluoropyridin-3-yl)methanol (430 mg, 3.4 mmol) in anhydrous dichloromethane (30 mL) was added dropwise phosphorus tribromide (650 muL, 6.8 mmol). The mixture was stirred at room temperature overnight. Dichloromethane was evaporated. The residue was dried in vacuo, affording 3-(bromomethyl)-5- fluoropyridine hydrobromide. The product was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22620-32-2, (5-Fluoropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75291-85-9 , The common heterocyclic compound, 75291-85-9, name is 5-Bromo-2-chloronicotinamide, molecular formula is C6H4BrClN2O, 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.

General procedure: To 1,4-dioxane (30 mL) were added tert-butyl piperazine-1-carboxylate (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol) sequentially. The mixture was heated to 110 C, after stirring for 12 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (3.15 g, 88.7%).; The title compound was prepared using 5-bromo-2-chloronicotinamide (1.50 g, 6.37 mmol), tert-butyl piperazine 1-carboxylate (1.19 g, 6.37 mmol) and potassium carbonate (3.52 g, 25.48 mmol) in acetonitrile (20 mL) according to the process described in Step 4 of Example 1, and the crude product was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (2.25 g, 91.8%).MS (ESI, pos. ion) m/z: 385.2 [M+H] and?H NMR (400 IVIFIz, DMSO-d6): (ppm) 8.31 (d, J= 2.4 Hz, 1H), 7.95 (s, 1H), 7.82 (d, J= 2.0 Hz, 1H), 7.63 (s, 1H), 3.42 (d, J= 4.8 Hz, 4H), 3.27 (d, J= 4.8 Hz, 4H), 1.41 (s, 9H).

The synthetic route of 75291-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; LIANG, Haiping; YI, Chao; ZHANG, Ji; (94 pag.)WO2016/192657; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem