Category: pyridine-derivatives

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. 39903-01-0, name is 2-Amino-5-bromo-3-pyridinol. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Amino-5-bromo-3-pyridinol

To a mixture of 2-amino-5-bromopyridin-3-ol (5.00 g, 23.5 mmol, CAS 39903-01- 0) in DME (50.0 mL) was added NaOH (3.00 g, 75.0 mmol) in H20 (30.0 mL) dropwise at 10 ~ 20 C. The reaction mixture was degassed under vacuum and chloro(difluoro)m ethane (15.0 psi) was passed through the reaction mixture at 10 ~ 20 C and the mixture was stirred for 16 h. The reaction mixture poured into H20 (100 mL), then extracted with ethyl acetate (50.0 mL x 4). The combined organic layers were washed with brine (100 mL), dried over Na2S04, and concentrated under reduce pressure to get a residue. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate = 1/0 to 0/1) to give 5- bromo-3-(difluoromethoxy)pyridin-2-amine (1.70 g, 6.20 mmol, 26% yield) as a yellow solid. LC-MS (ESI+) m/z: 238.7 (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, 39903-01-0, 2-Amino-5-bromo-3-pyridinol.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-18-9, 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. 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

1-Trimethylsilyl-2-(2-ethylthio-4-trifluoromethylphenyl)ethyne (794 mg), 3-amino-2-chloro-5-trifluoromethylpyridine (650 mg, 1.1 Eq), triethylamine (1 mL), diphenylphosphino ferrocene dichloropalladium (141 mg), copper iodide (33 mg), DMF (5 mL) and a 1 M THF (tetrahydrofuran) solution (4 mL) of tetrabutylammonium fluoride were mixed, and the mixture was heated at reflux under argon for 4 hours. The reaction mixture was concentrated and the resulting residue was subjected to column chromatography to give the desired compound, i.e., 2-(2-ethylthio-4-trifluoromethylphenyl)ethynyl-5-trifluoromethylpyridin-3-amine (0.54 g). The obtained compound was dissolved in DMF (3 mL), potassium t-butoxide (672 mg, 3 Eq) was added to the solution, and the mixture was heated at 100 C. with stirring for 3 hours. After the reaction mixture was allowed to cool down to room temperature, silica gel was added and the mixture was concentrated. The residue was subjected to column chromatography to give 2-(2-ethylthio-4-trifluoromethylphenyl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; Yonemura, Ikki; Sano, Yusuke; Suwa, Akiyuki; Fujie, Shunpei; US2018/352811; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, 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, Quality Control of 5-Bromo-2-methoxyisonicotinaldehyde, blongs to pyridine-derivatives compound. Quality Control of 5-Bromo-2-methoxyisonicotinaldehyde

The solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (CAS: 936011-17-5, Vendor: Bide, 25.00 g, 115.72 mmol) and ammonium acetate (4.46 g, 57.86 mmol) in nitroethane (150 mL) was stirred at 100 C for 16 hrs. After being cooled down, the mixture was concentrated and purified by flash column (PE/EA = 10/1) to give compound 70a (23.00 g) as a green solid. MS: calc?d 273 (MH+), measured 273 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DEY, Fabian; KOU, Buyu; LIU, Haixia; SHEN, Hong; WANG, Xiaoqing; ZHANG, Weixing; ZHANG, Zhisen; ZHANG, Zhiwei; ZHU, Wei; (203 pag.)WO2019/238616; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 875781-18-3, 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. 875781-18-3, name is 5-Bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below.

5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine ((II), 10.44 g, 32.2 mmol) was combined with DMF, MeOH and triethylamine (75 mL each). The vessel was evacuated and flushed with argon (4x). XantPhos (1.12 g, 1.93 mmol) and Pd(OAc)2 (217 mg, 0.97 mmol) were added and carbon monoxide (generated from formic acid and sulfuric acid) was bubbled through the solution while heating to 60 C. The mixture was stirred under an atmosphere of carbon monoxide (balloon) for 8 h. Every 1.5 h carbon monoxide was bubbled through the solution for 5 minutes. The mixture was concentrated under reduced pressure and the residue was triturated with 2N HCl. The solids were heated at 95 C in about 100 mL 1N NaOH overnight. After cooling to RT, the mixture was acidified with conc. HCl and the precipitate collected by suction filtration and washed with water. The solids were dried in an oven at 110 C to constant mass. The solids were sonicated in 100 mL of toluene for 5 minutes and stirred for 30 minutes. The product was filtered, washed with an additional 20 mL of toluene and dried at 110 C. Yield: 7.92 g HPLC purity: > 99 %, 1H NMR (200 MHz, DMSO) delta 8.64 (d, J = 7.9 Hz, 2H), 5.69 (bs, 1H); 13C NMR (50 MHz, DMSO) delta 163.27, 150.97, 149.67, 136.69, 132.65, 115.73, 113.6; [M-H]- = 239.9 / 241.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,875781-18-3, 5-Bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; HEPAREGENIX GMBH; PRAEFKE, Bent; KLOeVEKORN, Philip; SELIG, Roland; ALBRECHT, Wolfgang; LAUFER, Stefan; (157 pag.)WO2019/149738; (2019); 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, 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. Recommanded Product: Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

With the rapid development of chemical substances, we look forward to future research findings about 1149-24-2.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
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. 936841-69-9, name is 4-(Trifluoromethyl)picolinonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 4-(Trifluoromethyl)picolinonitrile

To a solution of 4-(trifluoromethyl)pyridine-2-carbonitrile (0.516 g, 3.00 mmol) in methanol (4.5 ml) was added sodium methoxide (30 wt% in MeOH) (0.027 g, 0.150 mmol, 0.028 ml). The mixture was stirred at room temperature for 3 h. The solution was transferred into a reaction vial, methylamine (33 wt% inEtOH) (1.512 g, 16.07 mmol, 2.0 ml) was added, the vial was closed and the mixture was heated at60C overnight. Hydrochloric acid (4M in dioxane) (3.00 mmol, 0.750 ml) was added and heating was continued at 90C for 2 h. The reaction mixture was concentrated. In a reaction vial, the residue was redissolved in methylamine (33 wt% in EtOH) (7.56 g, 80 mmol, 10.00 ml), hydrochloric acid (4M in dioxane) (3.00 mmol, 0.750 ml) was added, the vial was capped and the mixture was heated at 90Covernight. The reaction mixture was concentrated and the residue partitioned between diethyl ether and sat. Na2CO3 (aq). After washing and separation of the phases, the aqueous layer was extracted with ether two more times. The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (0-100% B in A; A: CH2CI2 B: CH2CI2/MeOH/Et3N, 9/1/0.1). The fractions containing product were combined andconcentrated. The residue was dissolved in methanol and hydrochloric acid in dioxane (4M, 2 ml) was added. The mixture was concentrated, coevaporated with methanol and twice with diethyl ether to afford the title compound (484 mg) as a solid. LCMS (method 1): 218 (M+H), retention time 1.47 mm. 1H-NMR (DMSO-d6, ppm) 2.86 (3H), 3.06 (3H), 8.15 (1H), 8.29 (1H), 9.09 (1H), 9.87 (1H), 10.23 (1H).

The synthetic route of 936841-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; TITULAER, Ruud; EMERY, Daniel; EDMUNDS, Andrew; STOLLER, Andre; JUNG, Pierre Joseph Marcel; BUCHHOLZ, Anke; RENOLD, Peter; (98 pag.)WO2015/144826; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1221171-70-5 ,Some common heterocyclic compound, 1221171-70-5, molecular formula is C6H3ClF3NO, 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 solution of LDA (2 M, 2.5 mL) in THF ( 27.0 mL) was added dropwise a solution of 2-chloro-6-(trifluoromethoxy)pyridine (900 mg, 4.6 mmol) in THF (9.0 mL) at -78C under N2. The mixture was stirred at -78C for 2 h. A solution of I2 (1.3 g, 5.0 mmol, 1.0 mL) in THF (9.0 mL) was added at -78C. Then the mixture was slowly warmed to 25C and stirred for 12 h. The reaction was quenched with saturated H4C1 (15.0 mL) and extracted with ethyl acetate (15.0 mL chi 3). The combined organic phase was washed with brine (15 mL chi 3), dried over anhydrous Na2S04, filtered and concentrated to give a residue. The residue was purified by prep-TLC (Si02) to give 6-chloro-3-iodo-2-(trifluoromethoxy)pyridine (1.2 g, 3.0 mmol, 65.2% yield). 1H MR (400MHz, CHLOROFORM-i ) delta 8.10 (d, J= 8.1 Hz, 1H), 7.03 (d, J= 8.1 Hz, 1H).

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. 1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (184 pag.)WO2018/222918; (2018); 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, the common compound, a new synthetic route is introduced below. Safety of Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

The synthetic route of 1149-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine, 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, COA of Formula: C5H2ClFN2O2, blongs to pyridine-derivatives compound. COA of Formula: C5H2ClFN2O2

General procedure: To a solution of Compound 4 (2 g, 8.58 mmol, 1 eq) in CH3CN (30 mL) was added CS2CO3 (5.59 g, 17.15 mmol, 2 eq) in one portion at 20 C. After stirring at 20 C for 30 min, 2,3- dichloro-5-nitro-pyridine (1.82 g, 9.43 mmol, 1.1 eq) was added. The mixture was stirred at 20 C for 36 h. The reaction mixture was filtered and the filter cake was washed with 100 mL of EtOAc. The filter cake diluted with water (100 mL) and extracted with DCM (3 x 150 mL). The combined DCM extracts were washed with aq saturated NaCl (10 mL), filtered, and concentrated under reduced pressure to give crude Compound 6 as a yellow solid (1.8 g, 53.85% yield). 1H NMR (400 MHz, DMSO-d6) d 9.03 (d, 1H), 8.99 – 8.95 (m, 2H), 8.26 (s, 1H), 7.64 (s, 1H), 7.42 (d, 1H), 3.99 (s, 3H), 3.82 (s, 3H); MS (El) for C17H12CIN3O6, found 389.9 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53554-20-4, 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. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile. A new synthetic method of this compound is introduced below.

38 (500mg, 3.25mmol), phenylboronic acid (595mg, 4.88mmol), K3PO4 (1.73g, 8.14mmol) and Pd(PPh3)4 (0.16mmol) were added to a microwave vial together with toluene/ EtOH (10:1, 11mL). The vial was flushed with N2, sealed and heated under microwave irradiation for 1h at 100C. The reaction mixture was cooled to rt, 1M NaOH (30mL) was added, and the mixture was extracted with EtOAc (2×30mL). The combined organic phase was dried over Mg2SO4 and evaporated under vacuum. Purification by DCVC (heptane/EtOAc 100:0 to 60:40) afforded the product as yellow solid (416mg, 65%). mp 204.1-204.9C. 1H NMR (CDCl3) delta 7.89-7.83 (m, 2H), 7.75 (d, J=8.8Hz, 1H), 7.54-7.47 (m, 3H), 6.50 (d, J=8.8Hz, 1H). 13C NMR (DMSO-d6) delta 161.0, 141.6, 138.0, 129.5, 128.4, 128.2, 119.7, 106.6, 92.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53554-20-4, 6-Amino-2-chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem