Category: pyridine-derivatives

Reference of 189230-41-9, 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. 189230-41-9, name is 2-Bromopyridine-3,4-diamine. A new synthetic method of this compound is introduced below.

Step 2: To a solution of 2-fluoro-6-iodobenzaldehyde (1.5 g, 6.0 mmol) and 2-bromopyridine-3, 4- diamine (1.1 g, 6.0 mmol) in ethanol (20 mL), was added ferric chloride (778 mg, 4.80 mmol). The reaction mixture was stirred at 60 C under oxygen atmosphere overnight. The next day, solvent was evaporated via rotavap and theresulting residue was purified by column chromatography on silica gel eluting with petroleum/ethyl acetate (3 :1) to give the desired product (1.6 g, 64% yield) as a yellow solid. LCMS (ESI) m/z: 418 [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,189230-41-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LAI, Yingjie; LIANG, Jun; MAGNUSON, Steven, R.; ROBARGE, Kirk, D.; TSUI, Vickie, Hsaio-Wei; ZHANG, Birong; WO2013/41539; (2013); 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C7H6F3NO

Step a: To a -78 C solution of diisopropylamine (0.966 mL, 6.77 mmol) in THF (20 mL) was added n-BuLi (1.6 M in hexanes, 4.23 mL, 6.77 mmol) dropwise and the reaction mixture was stirred for 5 mm at -78 C. A solution of 2-methoxy-3- (trifluoromethyl)pyridine (1.2 g, 6.77 mmol) in THF (10 mL) was added and the resulting mixture was stirred for 2 h at -78 C. ?2 (1.72 g, 6.77 mmol) in THF (5 mL) was added at -78 C and the resulting mixture was allowed to warm to RT within 30 mm and was further stirred at this temperature for 30 mm. The volatiles were removed under reduced pressure, the residue was dissolved in Et20 (200 mL) The organic layer was washed sequentially with sat. aq. Na25203 (200 mL), sat. aq. NH4C1 (200 mL), and sat. aq. NaHCO3 (200 mL), dried over Mg504, filtered, and the volatiles were removed under reduced pressure. The residue was purified by silica chromatography (0 to 25% gradient of EtOAc/heptane) to give 4-iodo-2-methoxy-3- (trifluoromethyl)pyridine (540 mg, 1.354 mmol). MS m/z 304.0 (M+H).

The synthetic route of 121643-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEN, Zhuoliang; FORTANET, Jorge Farcia; LAMARCHE, Matthew J.; SENDZIK, Martin; TAMEZ, JR., Victoriano; YU, Bing; (237 pag.)WO2016/203405; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 850663-54-6, 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. 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

A suspension of 2-hydroxy-4-chloro-5-nitropyridine (86.2 mmol, 15 g) in phosphorus oxychloride (50 mL) was heated at 80C for 3.5 hours. The excess phosphorus oxychloride was removed under reduced pressure and the residue partitioned between dichloromethane and 10% aqueous sodium carbonate solution. The aqueous phase was further extracted with dichloromethane (3 x 100 mL) . The combined organic extracts were dried (MgS04) then concentrated under reduced presssure to give the title compound as dark oil which solidified on standing (7.19 g, 43%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60753-14-2, 4-(Pyridin-3-yl)butan-1-ol, 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: C9H13NO, blongs to pyridine-derivatives compound. HPLC of Formula: C9H13NO

Step A 4-pyridin-3-yl-butyraldehyde To a solution of oxalyl chloride (0.74 mL in 5 mL dry methylene chloride) at -78 C. was added a solution of methyl sulfoxide (0.90 mL in 5 mL methylene chloride) and the mixture stirred at low temperature for 15 minutes. A solution of 4-pyridin-3-yl-butan-1-ol (prepared essentially as described in Example 2.1, 820 mg in 10 mL methylene chloride) and the reaction allowed to proceed for 45 minutes after which time 4 mL triethylamine were added and the mixture allowed to warm to room temperature. After 35 minutes saturated sodium bicarbonate was addded and the mixture extracted with methylene chloride. The organic portion was washed with saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo to give the crude title compound (813 mg).

The synthetic route of 60753-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5849764; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 799293-73-5, Adding some certain compound to certain chemical reactions, such as: 799293-73-5, name is 3-Bromofuro[3,2-c]pyridin-4-amine,molecular formula is C7H5BrN2O, 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 799293-73-5.

-(4-aminofuror3,2-clpyridin-3-yl)-2,3-dihvdro-1 H-indole-1-carboxylateA mixture of 3-bromofuro[3,2-c]pyridin-4-amine (3.002 g, 14.09 mmol), 1 ,1 -dimethylethyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-indole-1-carboxylate (5.346 g, 15.48 mmol), and PdCI2(dppf)-CH2CI2 adduct (0.573 g, 0.702 mmol) in 1 ,4-Dioxane (120 ml.) and saturated aqueous sodium bicarbonate (43 ml_, 43.0 mmol) was degassed with Nitrogen for 20 minutes. The mixture was then stirred at reflux under Nitrogen for 16 hours. It was then cooled, poured into half-saturated aqueous NaHC03 (250 ml_), and extracted with ethyl acetate (2 250 ml_). The extracts were washed with brine (1 * 250 ml_), dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (Analogix, 400 g Si02, 20%-100% EtOAc in hexanes gradient over 60 minutes, then 100% EtOAc for 15 more minutes) to give 1 , 1 -dimethylethyl 5-(4- aminofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1 H-indole-1 -carboxylate (3.93 g) as an off-white solid. LC/MS (ES) m/z = 352 [M+H]+.

According to the analysis of related databases, 799293-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 123853-39-4 ,Some common heterocyclic compound, 123853-39-4, molecular formula is C16H15Cl2NO4, 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.

Step 1 preparation of intermediate 2.0 kg (5.61mol) inputs 10L in acetonitrile, inputs under stirring chloro-butyrate 850g (6.22mol) and potassium carbonate 860g (6.22mol), heating to reflux reaction 4-6h, cooling to room temperature, filter, filtrates in 40-50 C concentrated under reduced pressure to dry, subsequently joined 4L ethyl acetate, reflux is dissolved, and 45g activated carbon decolourizations 5-15min, hot filtering, filtrates in 30-40 C dropwise 7L-hexane crystallization, filtration, 40-50 C decompression drying to obtain the butyric acid clevidipine 2.38 kg, yield 92.89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,123853-39-4, its application will become more common.

Reference:
Patent; Hefei long promise Pharmaceutical Technology Co; Wu, biao; Ling, lin; Wang, zhouhong; Dai, yij; (10 pag.)CN105461619; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55052-27-2, 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. 55052-27-2, name is 6-Chloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5ClN2, 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.

The title compound of Preparation 57 (1.00 g, 6.55 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (1.0 ml, 7.2 mmol) and potassium carbonate (2.72 g, 19.7 mmol) were suspended in 13 ml dimethoxyethane in a microwave reactor and submitted to three vacuum-argon cycles. [1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (0.29 g, 0.33 mmol) was added and the resulting mixture was submitted to three further vacuum-argon cycles. The mixture was stirred at 120ºC for 2h under microwave irradiation. The mixture was allowed to cool and was filtered through Celite, eluting with ethyl acetate. The filtrate was evaporated under reduced pressure and the residue was purified using the Isolera Purification System (ethyl acetate-hexane gradient, 0:100 rising to 50:50) to give 0.57 g (4.31 mmol, 65%) of the title compound as a beige solid. Purity 98%. [0443] 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 10.87 (br. s., 1 H), 7.86 (d, J=7.63 Hz, 1 H), 7.29 (dd, J=3.52, 2.35 Hz, 1 H), 6.97 (d, J=7.63 Hz, 1 H), 6.47 (dd, J=3.52,1.76 Hz, 1 H), 2.69 (s, 3 H). [0444] HPLC/MS (15 min) retention time 2.57 min. [0445] LRMS:m/z133(M+1).

According to the analysis of related databases, 55052-27-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Alonso Diez, Juan Antonio; Buil Albero, Maria Antonia; Eastwood, Paul Robert; Esteve Trias, Cristina; Lozoya Toribio, Maria Estrella; Roberts, Richard Spurring; Vidal Gispert, Laura; EP2548876; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 23056-47-5, 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. 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine. A new synthetic method of this compound is introduced below.

Into a 2L 3-necked round-bottom flask under N2 atmosphere, was placed 2-bromo- 4-methyl-5-nitropyridine (100 g, 460.79 mmol, 1 equiv), methyl 2,2-difluoro-2- (fluorosulfonyl)acetate (177.0 g, 921.57 mmol, 2 equiv), and Cul (70.2 g, 368.60 mmol, 0.800 equiv) in DMF (1 L). The resulting solution was stirred for 14 h at 120 C and then diluted with NH4CI (3 L), NH4OH (0.5 L). The resulting solution was extracted with ethyl acetate and the combined organic layer was concentrated under reduced pressure. The residue was applied onto a silica gel column and eluted with petroleum ether to give (40 g, 41.94%) of the title compound as a red oil. GC-MS: (ES, m/z): [M]+ 206.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23056-47-5, 2-Bromo-4-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary, Plake; DILLON, Michael, Patrick; GONZALEZ-LOPEZ, Marcos; SUTTON, James, Clifford, Jr.; (248 pag.)WO2019/156987; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1137-67-3 ,Some common heterocyclic compound, 1137-67-3, molecular formula is C12H9N3, 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: 2-Substituted benzimidazole (0.01 M) was added to the ethanolic solution of benzamide (0.01M). Formaldehyde (37-41% w/v) (0.01 M) was added and the reaction mixture was then adjusted to the pH of 3.5 with concentrated HCl. The mixture was kept at efficient ice cooling for half an hour. Then, it was refluxed with stirring at 80 C for 10-12h. Formaldehyde (37-41% w/v) was added to the reaction mixture in portions for completion of the reaction. End of reaction was monitored by TLC. Reaction mixture was kept in refrigerator overnight. Solvent was evaporated under reduced pressure and product was collected, washed with water and recrystallized from ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1137-67-3, its application will become more common.

Reference:
Article; Sethi, Ritchu; Arora, Sandeep; Saini, Deepika; Singh, Thakur Gurjeet; Jain, Sandeep; Acta poloniae pharmaceutica; vol. 74; 5; (2017); p. 1413 – 1425;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19842-08-1, 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 19842-08-1 as follows.

In a 2 L round-bottomed flask was charged n-butyllithium 2.5M hexanes (99 ml, 248 mmol) in Et2O (1680 ml) to give a colorless solution. The reaction was cooled to -78 C. n-Butyllithium 2.5M hexanes (99 ml, 248 mmol) was added dropwise keeping the temperature below -70 C. The reaction was stirred for 1 hour and N,N-dimethylformamide (36.6 ml, 473 mmol) was added keeping the temperature below -70 C. The reaction was stirred for 1 hour and quenched with saturated ammonium chloride solution (2 L). The organic layer was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure. The crude residue was purified by column chromatography eluting with 0-30% ethyl acetate to give 6-bromonicotinaldehyde. Yield 19.7 g, 44.8%In a 2 L round-bottomed flask was added Methyltriphenylphosphonium bromide (42.9 g, 120 mmol) in THF (600 ml) and cooled to -20 C. n-Butyllithium 2.5M hexanes (48.0 ml, 120 mmol) was added dropwise keeping the temperature below 0 C. The reaction was warmed to room temperature for 20 minutes and cooled back to 0 C. A solution of 6-bromonicotinaldehyde (18.6 g, 100 mmol) in THF (40 mL) was added. The reaction was warmed to room temperature and stirred overnight. The reaction was partitioned between water and diethyl ether (1 L) and the organic layer was dried over sodium sulfate, filtered and solvent removed at room temperature under reduced pressure. The product, 2-bromo-5-vinylpyridine, was purified by bulb to bulb distillation (600 mTorr, 80-100 C.). Yield 17.2 g, 93%2-Bromo-5-vinylpyridine (17.2 g, 40.1 mmol) was dissolved in ethanol (150 mL) and Adam’s Catalyst (PtO2, 75%, 1.4 g) was added. The mixture was hydrogenated at 3 psi of hydrogen, continually checking the progress of the reaction by LC and 1H NMR between each charge of hydrogen. After 10 psi was consumed, the data showed completion of the reaction with <5% of reduction of the bromine. The catalyst was filtered off and the solvent was removed under reduced pressure at 20 C. to give 2-bromo-5-ethylpyridine. Yield 17 g, 98%.In a 1 L round-bottomed flask was compound 6 (10 g, 53.8 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (13.83 g, 59.1 mmol) in Dioxane (300 ml) followed by saturated sodium bicarbonate (150 ml). The mixture was degassed by passing a stream of nitrogen through the mixture for 20 minutes. Tetrakis(triphenylphosphine) palladium(0) (3.36 g, 2.91 mmol) was added and the mixture was heated to reflux becoming very thick then finally going to solution. The reaction was heated for 2 hours, cooled to room temperature and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure. The residue was purified by column chromatography 0-100% ethyl acetate/heptane to give 3-(5-ethylpyridin-2-yl)-4-methylaniline. Yield 8.7 g, 77%The urea was formed from 3-(5-ethylpyridin-2-yl)-4-methylaniline and 4-(2-amino-5-tert-butylthiophene-3-carbonyl)-3,3-dimethylpiperazine-2-one. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19842-08-1, its application will become more common. Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem