Pyridine-derivatives

Reference of 127561-18-6, 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. 127561-18-6, name is 1-(6-(Trifluoromethyl)pyridin-2-yl)piperazine. A new synthetic method of this compound is introduced below.

A-9 (0.33g, 1.40mmol), C-1 (0.30g, 1.30mmol),Triethylamine Anhydrous(0.263 g, 2.60 mmol) was dissolved in 25 mL of anhydrous acetonitrile, and HATU (0.513 g, 1.40 mmol) was added, and the reaction was performed at room temperature for 30 min. After the reaction, it was diluted with water, extracted with ethyl acetate, washed with dilute hydrochloric acid, washed with sodium bicarbonate solution, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated and purified by silica gel column chromatography (PE: EA = 2: 1, v / v) to obtain 470.385 g of the compound with a yield of 66.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,127561-18-6, 1-(6-(Trifluoromethyl)pyridin-2-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Weitan Pharmaceutical Technology Co., Ltd.; Cheng Yunfeng; Hu Yongzhou; (45 pag.)CN110357833; (2019); A;,
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 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Bromo-1H-pyrrolo[3,2-b]pyridine

To a mixture of 6-bromo-lH-pyrrolo[3,2-b]pyridine (0.985 g, 5 mmol, 1 eq) in N,N- dimethylformamide (25ml) was added cesium carbonate (1.79 g, 5.5 mmol, 1.1 eq), followed by (1,4,4- trifluorocyclohexyl)methyl trifluoromethanesulfonate (1.50 g, 5 mmol, 1 eq). The mixture was stirred at 70 C for five hours. The mixture was quenched with water, and extracted with ethyl acetate which was washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated down. The sample was purified by flash chromatography eluting with 40% ethyl acetate in hexane, then triturated with hexanes to provide 1.63 g (93.9%) of product as a solid (24, 1.63 g, 93.9%), MS (ESI) [M+H+]+ = 347.0, 349.0.

With the rapid development of chemical substances, we look forward to future research findings about 944937-53-5.

Reference:
Patent; ZHANG, Jiazhong; BUELL, John; CHAN, Katrina; IBRAHIM, Prabha, N.; LIN, Jack; PHAM, Phuongly; SHI, Songyuan; SPEVAK, Wayne; WU, Guoxian; WU, Jeffrey; WO2014/145051; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 78607-36-0 , The common heterocyclic compound, 78607-36-0, name is 2-Chloro-3-iodopyridine, molecular formula is C5H3ClIN, 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.

2-chloro-3-iodopyridine (500 mg, 2.09 mmol) was placed under argon and dissolved in anhydrous 9 THF (10 ml). 10 Et3N (1.44 ml, 5 eq, 10 mmol) and 11 1-ethoxy-4-ethynylbenzene (365 mg, 1.2 eq, 2.5 mmol) were added, followed by 12 CuI (10 mg, 0.025 eq, 0.05 mmol) and 13 PdCl2(PPh3)2 (37 mg, 0.025 eq, 0.05 mmol). The dark brown mixture was stirred at r.t. for 3 h, before 14 water (20 ml) and 15 CH2Cl2 (20 ml) were added. The aqueous layer was extracted with CH2Cl2 and the organic extracts were washed with water and brine, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography (PE:EtOAc 85:15) to afford the desired 26 compound (440 mg, 82%). 1H-NMR (300 MHz, CDCl3): 1.43 (t, J=7.0 Hz, 3H), 4.06 (q, J=7.0 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 7.22 (dd, J=7.7, 4.8 Hz, 1H), 7.49 (d, J=8.8 Hz, 2H), 7.82 (dd, J=7.7, 1.9 Hz, 1H), 8.31 (dd, J=4.8, 1.9 Hz, 1H).

The synthetic route of 78607-36-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Institut National de la Sante et de la Recherche Medicale (INSERM); Centre National de la Recherche Scientifique (CNRS); Sorbonne Universite; Universite Claude Bernard Lyon 1; Dimanche-Boitrel, Marie-Therese; Bach, Stephane; Delehouze, Claire; Goekjian, Peter; Comte, Arnaud; (32 pag.)US2018/312502; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one, 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, HPLC of Formula: C7H5NOS, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5NOS

Preparation 125; 2- (thieno [3, 2-b] pyridin-7-yl) acetamide; 7-Bromo-thienoF3, 2-blpyridine; Heat phosphorus oxybromide (145.00 g, 0.50 moles) to 60 C to form a melt. Add thieno [3, 2-b]-7-pyridinol (14.73 g, 97.43 mmol) while stirring and increase heat to 100 C for 2 hours. Pour the reaction contents over ice (1.0 kg). Dilute the slurry with ice and water to about 3 L. Extract the aqueous solution with chloroform (4 X 500 mL). Make the aqueous solution basic (pH 10-11) with 2 N sodium hydroxide and reextract with chloroform (3 X 400 mL). Treat the organic layers with magnesium sulfate, filter and concentrate. Redissolve the crude solid in dichloromethane (100 mL) and load the solution onto silica (300 g). Elute with 2 L of 30% ethyl acetate/dichloromethane. Concentrate the eluent to yield the desired compound as a crystalline solid (18.68 g, 89.5%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2003/76442; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 15862-36-9 ,Some common heterocyclic compound, 15862-36-9, molecular formula is C5H2Br2N2O2, 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.

B. 2-(3-Methoxyphenyl)-5-nitro-3-phenylpyridineObtained (0.257 g, 87% of yield) following the procedure described in Intermediate 2 (step A) starting with 3-bromo-2-(3-methoxyphenyl)-5-nitropyridine (0.97 mmol, 0.300 g) and phenylboronic acid (1.07 mmol, 0.130 g).ESI/MS (m/e, %): 307 [(M+1)+, 100].C. 2-(3-Methoxyphenyl)-5-nitro-3-phenylpyridineObtained (0.258 g, yield 87%) following the procedure described in Intermediate 27, starting with 3-bromo-2-(3-methoxyphenyl)-5-nitropyridine (0.97 mmol, 0.300 g), phenylboronic acid (1.07 mmol, 0.130 g). delta 1H NMR (300 MHz, CDCI3): 3.64 (s, 3H), 6.89-6.99 (m, 3H), 7.21-7.24 (m, 3H), 7.32- 7.37 (m, 4H), 8.50 (s, 1 H), 9.47 (s, 1 H). ESI/MS (m/e, %): 307 [(M+1)+, 100].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15862-36-9, its application will become more common.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 918516-27-5, 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. 918516-27-5, name is 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C13H9ClN2, 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.

General procedure: 7-Azaindole derivatives (4.2 mmol) were added to a stirredsuspension of AlCl3 (21.0 mmol, 2.80 g) in DCM (40 mL) placed at icebath. After the mixture was stirred at room temperature for 0.5 h,acetyl chloride (21.0 mmol, 1.49 mL) was added dropwise and theresulting mixture was reacted for 12 h at room temperature. MeOH(20 mL) was added cautiously to quench the reaction, the solventswere removed under reduced vacuum. Then the residue was dissolvedin 40 mL water,1N NaOH (aq) was added to adjust the pH upto 5, and extracted with ethyl acetate (15mL 3). The combinedorganic phase was dried over anhydride sodium sulfate andconcentrated under reduced vacuum. The residue was further purifiedby column chromatography on silica gel using PE/EA as eluentto afford the corresponding acylated product

According to the analysis of related databases, 918516-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Bin; Yuan, Xia; Xu, Bo; Zhang, Han; Li, Ridong; Wang, Xin; Ge, Zemei; Li, Runtao; European Journal of Medicinal Chemistry; vol. 170; (2019); p. 1 – 15;,
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. 76006-13-8, name is 3-Bromo-1H-pyrazolo[3,4-c]pyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4BrN3

A mixture of 2-chloro-6-(trifluoromethyl)benzyl 4-methylbenzenesulfonate (A-2) (0.19 g, 0.51 mmol), 3-bromo-lH-pyrazolo[3,4-c]pyridine (A-3) (0.1 g, 0.51 mmol), t-BuOK (0.11 g, 1.02 mmol) and TBAI (75 mg, 0.20 mmol) in THF (5 ml) was heated at 60 C for 14h. The reaction mixture was cooled down, diluted with saturated NH4C1 solution (20 ml) and extracted with ethyl acetate (30 ml x2). The combined organic layers were washed with brine (20 ml), dried over anhydrous Na2S04 and concentrated to give the title compound A-4 as a brown oil. LCMS (ESI) calc’d for Ci4H8BrClF3N3 [M+H] +: 390, found: 390

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, 76006-13-8, 3-Bromo-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28591; (2014); 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 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

5-(4-Methylpiperazin-1-yl)pyridin-2-amine (35.6 mg, 0.185 mmol) was taken up in dry1 ,4-dioxane (2 mL) under argon. tert-Butyl 1 -(2-chloropyrimidin-4-yl)-2-oxo- 1,3 – diazaspiro[4.Sjdecane-3-carboxylate (4) (65 mg, 0.18 mmol) was added followed by cesiumcarbonate (0.173 g, 0.532 mmol) and rac-2,2?-bis(diphenylphosphino)-l,l?-binaphthyl (11.0 mg, 0.0177 mmol). Finally, palladium acetate (3.98 mg, 0.0177 mmol) was added and the mixture was sparged with argon for 20 mm, the flask fitted with a condenser and the reaction mixture heated at 100 C for 30 minutes. The reaction mixture was cooled to ambient temperature, filtered through a pad of Celite rinsing with ethyl acetate and the solvent wasremoved in vacuo to afford a dark yellow foam. Addition of water caused the product to precipitate. The solids were removed by filtration and washed with water. Drying under nitrogen affords 52 mg (56% yield) of the desired product 5 as a dark yellow solid.MS (ESI+) for C27H38N803 m/z 523.6 (M+H)5

With the rapid development of chemical substances, we look forward to future research findings about 571189-49-6.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; GASTON, Ricky, D.; GADWOOD, Robert, C.; (177 pag.)WO2018/5533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58584-92-2, 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 58584-92-2 as follows.

To a 0.3 M solution of amino acid (1 equiv) in anhydrous THF, under an inert atmosphere, was added thionyl chloride (3.3 equiv) in a dropwise fashion. The reaction mixture was stirred at room temperature for 2 hours. After this time the reaction was concentrated in vacuo to give a crude yellow solid residue. The crude solid was dissolved in THF (equal to initial reaction volume) and concentrated in vacuo again to give a yellow solid residue. The residue was dissolved once more in THF and concentrated as before to give a solid residue which was then dissolved in THF (to give a solution of 0.3M) and ammonia gas bubbled through the solution for 1 hour. The resultant precipitate was removed by filtration and the filtrate concentrated in vacuo to give a yellow precipitate which was triturated with water at 50 0C then dried to give the title compound (typically 90-95 %) yield and suitably clean enough to be used without any further purification.2-Amino-6-chloronicotinamide – X=N, Y=C, Z=C: (92 % yield, 93 % purity) m/z (LC-MS, ESP): 172 [M+H]+ R/T = 3.19 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58584-92-2, its application will become more common.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2008/23161; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1056162-06-1, 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. 1056162-06-1, name is (2-(Trifluoromethyl)pyridin-3-yl)methanamine, molecular formula is C7H7F3N2, 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 mixture of 4-chloro-N-isopropyl-1 ,8-naphthyridin-2-amine (150 mg, 676.6 umol, 1 eq) and [2-(trifluoromethyl)-3-pyridyl]methanamine (1.2 g, 6.8 mmol, 10 eq) was stirred at 180C for 0.5 hour under microwave and N2. TLC (EtOAc) showed that 4~chloro- N-isopropyl-1 ,8-naphthyridin-2-amine was consumed completely and several new spots. LCMS showed that several peaks and 20% of desired product. To the mixture was added water (40 mL) and extracted with EtOAc (40 mL*2). The organic layers were washed with brine (40 mL), dried over NaaSCU and concentrated. The residue was purified by prep-TLC (EtOAc). Then the crude product was further purified by prep-HPLC (Column: Phenomenex Synergi C18 150*30mm*4um; Condition: water(0.225%FA)-ACN). The salt product was basified by strong basic anion exchange resin. Then the residue was purified by prep-TLC (Dichloromethane: Methanol 10: 1) to obtain N2-isopropyi-N4-[[2-(trifluoromethyi)-3- pyridyl]methyl]-1 ,8-naphthyridine-2,4-diamine (5.4 mg, 15 umo, 2% yield) as a light yellow solid.

According to the analysis of related databases, 1056162-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIVERPOOL SCHOOL OF TROPICAL MEDICINE; THE UNIVERSITY OF LIVERPOOL; EISAI R&D MANAGEMENT CO., LTD.; WARD, Stephen A.; TAYLOR, Mark J.; O’NEILL, Paul M.; HONG, Weiqian David; BENAYOUD, Farid; (300 pag.)WO2018/134685; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem