Category: pyridine-derivatives

Electric Literature of 5345-47-1 ,Some common heterocyclic compound, 5345-47-1, molecular formula is C6H6N2O2, 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 solution of bromine (7 mL, 136 mmol) in acetic acid (20 mL) was added dropwise to an acetic acid (230 mL) suspension of 2-aminonicotinic acid (9.37 g, 68 mmol) at 100C. After stirring the mixture for 6 hours, ether (600 mL) was added and the stirring was continued for 14 hours. The mixture was cooled to 00C, the precipitate was filtered, washed with ether and dried to give 18.2 g (90%) of a hydrobromide salt. The salt was dissolved in water (200 mL) and sodium hydroxide solution (60 mL, 2N) then neutralized with IN HCl. The resulting precipitate was filtered and dried to afford of the title compound (12.01 g, 82%). 1H NMR (300 MHz, OMSO-d6, delta): 8.25 (d, J= 2.6Hz, IH), 8.09 (d, J= 2.6Hz, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5345-47-1, its application will become more common.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/67416; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 173999-23-0 ,Some common heterocyclic compound, 173999-23-0, molecular formula is C6H7BrN2, 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.

Intermediate 21A. N-((5-bromopyridin-2-yl)methyl)-3,4-dichlorobenzamide[00211] 3,4-Dichlorobenzoic acid (0.50 g, 2.6 mmol), (5-bromopyridin-2- yl)methanamine (0.490 g, 2.62 mmol) and PyBOP (1.5 g, 2.9 mmol) were combined in dimethylformamide (10 mL) and treated with diisopropylethylamine (1.4 mL, 7.9 mmol). The reaction was stirred at rt for 2 h, concentrated and the residue purified on flash chromatography (4 g cartridge, 0 to 100 % ethyl acetate/hexanes) to afford 0.52 g of Intermediate 21 A (55% yield) as a white solid. LC/MS (HPLC Method M): RT = 2.00 min, (M+H)+ = 360.8. -bromo-3 -(3 ,4-dichlorophenyl)imidazo [ 1 ,5-a]pyridine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,173999-23-0, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; QIAO, Jennifer, X.; FINLAY, Heather; JIANG, Ji; LLOYD, John; HU, Carol Hui; PI, Zulan; TORA, George, O.; NEELS, James; HANGELAND, Jon, J.; FRIENDS, Todd, J.; WO2013/48928; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5350-93-6, Adding some certain compound to certain chemical reactions, such as: 5350-93-6, name is 6-Chloropyridin-3-amine,molecular formula is C5H5ClN2, 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 5350-93-6.

Bromine (24.86 g, 155.57 mmol) was added to a solution of6-chloropyridin-3-amine (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid(383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acidwas then evaporated. The residue was dissolved in EtOAc, washed with saturatedaqueous Na2C03, water and brine. The organic layer was dried over MgS04, filteredand evaporated, yielding 32.20 g of the desired product 49-a (99.8percent). m/z = 206.96 (M+ It

According to the analysis of related databases, 5350-93-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; TAHRI, Abdellah; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; VENDEVILLE, Sandrine Marie Helene; HU, Lili; DEMIN, Samuel Dominique; Cooymans, Ludwig Paul; WO2013/186333; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16830-24-3 ,Some common heterocyclic compound, 16830-24-3, molecular formula is C8H9NO2, 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 solution of (NH4)25208 in water was added to a solution of methyl 2-methylpyridine-4-carboxylatein methanol at reflux. The resulting reaction mixture was then stirred at reflux. Aqueous work up andrecrystallization from DCM afforded the title compound as white solid. ?H-NMR (300 MHz, CDC13): oe7.60 (s, 2 H), 4.78 (s, 2 H), 3.93 (s, 3 H), 3.81 (s (br), 1 H), 2.61 (s, 3 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. 16830-24-3, Methyl 2-methylisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPITHERAPEUTICS APS; BOESEN, Thomas; LABELLE, Marc; YANG, Ying; SARASWAT, Neerja; DUDEKULA, Dastagiri; COOK, Cyril John; VAKITI, Ramkrishna Reddy; ZHANG, Rui; ULLAH, Farman; (316 pag.)WO2016/33169; (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. 882500-21-2, name is 5-Bromo-6-trifluoromethylpyridin-2-ylamine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrF3N2

A mixture of 5-bromo-6-(trifluoromethyl)pyridin-2-amine (3.0 g, 12.3 mmol), Zn(CN)2 (0.81 g, 6.9 mmol), Pd2(dba)3 (0.57 g, 0.6 mmol), and Xantphos (0.72 g, 1.2 mmol) in DMA (12 mL) was placed in a sealed tube. The mixture was degassed with argon and stirred at 160C for 20h. The mixture was poured into water and extracted with EtOAc (2x). The combined organic layers were dried over magnesium sulfate and concentrated to dryness. The residue was purified by column chromatography on silica gel eluting with 3: 1 EtOAc/hexanes to afford 1.9 g of 6-amino-2-(trifluoromethyl)nicotinonitrile as a solid. lR NMR (400 MHz, CDC13) delta 7.74 (d, 1H), 6.67 (d, 1H).

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, 882500-21-2, 5-Bromo-6-trifluoromethylpyridin-2-ylamine.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2011/103202; (2011); A2;,
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. 89570-82-1, name is 3-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine

A CEM-designed 10-mL pressure-rated vial was charged with POCl3(2 mL), 3-chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine (211 mg,1mmol), 4-methoxylbenzoic acid or analogous acid (1mmol). The mixture was irradiated in a CEM Discover Focused Synthesiser (150 W, 140C, 200 psi, 15min). The mixture was cooled to room temperature by passing compressed air through the microwave cavity for 2 min. It was poured into cold ice (40 mL) and the formed precipitate filtered. The crude solid was recrystallised from EtOH to give the title compound 2a and others. All the other compounds were synthesised according to the same procedure.

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, 89570-82-1, 3-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine.

Reference:
Article; Yang, Ming-Yan; Zhai, Zhi-Wen; Sun, Zhao-Hui; Yu, Shu-Jing; Liu, Xing-Hai; Weng, Jian-Quan; Tan, Cheng-Xia; Zhao, Wei-Guang; Journal of Chemical Research; vol. 39; 9; (2015); p. 521 – 523;,
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. 126325-47-1, name is 6-Bromo-2-methylpyridin-3-amine. A new synthetic method of this compound is introduced below., SDS of cas: 126325-47-1

A solution of 6-bromo-2-methylpyridin-3-amine (24 g, 128 mmol) and AcOH (14.7 mL 257 mmol) in MeOH (200 mL) was cooled to 0C, Br2 (36.9 g, 230.9 mmol, 11.9 mL) was added and stirred at 0C for 5 hours. The mixture was quenched with saturated aqueous Na2S03 (500 mL), extracted with ethyl acetate (300 mL x 3). The organic layer was washed with brine (200 mL), dried over Na2S04, and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ethenethyl acetate = 2:1) to afford 4,6-dibromo-2-methylpyridin-3-amine.

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, 126325-47-1, 6-Bromo-2-methylpyridin-3-amine.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; MARIGO, Mauro; (142 pag.)WO2019/121840; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84487-14-9, 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. 84487-14-9, name is 2-Bromo-3-nitropyridine-4-amine. A new synthetic method of this compound is introduced below.

To a solution of N1-(3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl)-N2,N2-dimethylethane-1,2-diamine (CVII) (2.00 g, 6.49 mmol, 1.2 eq), 2-bromo-3- nitropyridin-4-amine (CVIII) (1.18 g, 5.41 mmol, 1.0 eq), Na2C03 (1.15 g, 10.82 mmol, 2.0 eq) and Pd(dppf)Cl2 (395.73 mg, 540.83 muiotaetaomicron, 0.1 eq) in dioxane (40 mL) and H20 (8 mL) was degassed and then heated to 80C overnight under N2. TLC (PE:EtOAc=l : l) showed the starting material was consumed completely. The reaction mixture was poured into H20 (300 mL). The mixture was extracted with EtOAc (3 x 250 mL). The organic phase was washed with saturated brine (300 mL), dried over anhydrous MgSO i, concentrated in vacuum to give a residue, which was purified by silica gel column chromatography (PE/EtOAc=5/l) to afford N1-(3-(4-amino-3- nitropyridin-2-yl)-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (CIX) (1.50 g, 4.70 mmol, 86.9% yield) as a solid. ESIMS found for C15H18FN5O2 m/z 320.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,84487-14-9, 2-Bromo-3-nitropyridine-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (322 pag.)WO2016/40193; (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. 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of tert-Butyl (6-chloropyridin-3-yl)carbamate

tert-Butyl(6-chloro-4-(4-hydroxytetrahydro-2H-pyran-4-yl)pyridin-3- yl)carbamate. BuLi(2.166 mL, 5.70 mmol) was added to the diethyl ether (17 mL) solution of TMEDA(0.706 mL, 4.68 mmol) and tert-butyl (6-chloropyridin-3- yl)carbamate (0.4653g, 2.035 mmol) at -78 C. The reaction was stirred at this temperature for 1hour. Dihydro-2H-pyran-4(3H)-one (0.230 mL, 2.442 mmol) wasadded to the reaction mixture (at this moment, the bath temperature was -75C).The reaction was stirred for 2.5 hours before quenched with NH4CI (sat.). Thereaction was diluted with ethyl acetate and washed with water three times. Theorganic layer was separated, dried (Na2SC”4), filtered and concentrated.Flash column eluted with ethyl acetate in hexane from 0 to 25% to 50%> gavethe desired product (0.3600g, 45% yield, 83% pure). MS(ES+) m/e 329 [M+H]+.

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, 171178-45-3, tert-Butyl (6-chloropyridin-3-yl)carbamate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183208-35-7 , The common heterocyclic compound, 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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.

At room temperature, 400 ml of N,N-dimethylformamide was added to a 1 L three-necked flask to start stirring. Add 5_bromo-7-azaindole (30g, 0.15mol) and potassium tert-butoxide (25·6g, 0 · 23mol) to the reaction flask. After stirring and clearing, cool the ice bath to wait for the internal temperature. At 0 C, triisopropylsilyl chloride (43.3 g, 0.225 mol) diluted with 80 ml of tetrahydrofuran was initially added dropwise. After the addition is completed, the reaction is maintained at 0-5 C for 10-20 minutes. TLC control, the reaction is over. 300 ml of water was added to the reaction flask, and the mixture was stirred for 15 minutes. The aqueous phase was extracted with methyl tert-butyl ether (200 ml*2). The organic phase was combined and the organic phase was washed with 500 ml of saturated aqueous sodium chloride solution once. After drying over anhydrous sodium sulfate, the solvent is concentrated to obtain an oil, and 50 ml of methanol is added to precipitate a solid. The solid is vacuum filtered and dried to obtain a compound of the formula. Yield: 50.5 g, yield: 93.8%.

The synthetic route of 183208-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hongbozhiyuan Pharmaceutical Co., Ltd.; Zhuang Yinqiang; Peng Shaoping; Jiang Hui; (11 pag.)CN107434807; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem