Pyridine-derivatives

Application of 77992-44-0, Adding some certain compound to certain chemical reactions, such as: 77992-44-0, name is (5-Bromopyridin-2-yl)hydrazine,molecular formula is C5H6BrN3, 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 77992-44-0.

5-(methoxycarbonyl)-2-methylbenzoic acid (1.03 g, 5.32 mmol) was dissolved in 20 ml of 1 ,4-dioxane, followed by the dropwise addition of oxalyl chloride (0.464 ml, 5.32 mmol). The mixture was stirred at room temperature for 2 hours. The solution was then added dropwise to a suspension of 5-bromo-2-hydrazinopyridine (1.0 g, 5.3 mmol) in diisopropylethylamine (1.85 ml, 10.6 mmol) and 5 ml of dioxane at 0 0C. After 15 minutes, phosphorus oxychloride (0.974 ml, 10.6 mmol) was added and the reaction stirred at 100 0C overnight. The reaction was cooled, evaporated to about half the solvent volume and quenched with 100 ml of a NaHCO3 solution. The reaction mixture was extracted 2 times with 100 ml of ethyl acetate and the combined organic layers were washed with 100 ml of a NH4CI solution and 100 ml of brine, dried over MgSO4 and evaporated. The resulting residue was purified using silica gel chromatography to obtain a dark oil. The oil was triturated with 20 ml of ether and the resulting solid was dried in vacuo to give a tan solid (450 mg, 24% yield). 1H NMR (400 MHz, DMF-d?) delta 8.59 (s, 1 H), 8.19 (d, J= 1.5 Hz1 1H), 8.11 (dd, J= 8.1 , 1.7 Hz, 1 H), 7.89 (d, J= 9.4 Hz 1 H), 7.66 (d, J= 8.1 Hz, 1 H), 7.59 (dd, J= 9.7, 1.6 Hz, 1H), 3.90 (s, 3H), 2.32 (s, 3H); LC/MS, tr = 2.07 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min, at 254 nm, at 50 0C), ES-MS m/z 346 (M+H). ES- HRMS m/z 346.0212 (M+H calcd for C15H13BrN3O2 requires 346.0186).

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. 77992-44-0, (5-Bromopyridin-2-yl)hydrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/18735; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-15-6, 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 72587-15-6 as follows.

A microwave reaction vial was charged with 2-chloro-3-nitro-5- (trifluoromethyl)pyridine (2 g, 8.83 mmol), NMP (4.41 ml) and CuCN (0.830 g, 9.27 mmol). The vial was sealed and the mixture was irradiated in the MW at 175 C for 15 min. Upon cooling to RT, the reaction mixture was poured onto ice and EtOAc was added. The mixture was filtered through Celite, washing with EtOAc and a small amount of MeOH. The layers of the filtrate were separated, and the aqueous portion was extracted again with EtOAc. The combined organic portions were dried with sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography, using a gradient of 0-30% EtOAc in heptane to provide 3-nitro-5- (trifluoromethyl)picolinonitrile (645 mg, 2.97 mmol, 33.7 % yield) as a yellow oil that solidified upon standing. LC/MS (ESI) m/z = 218.1 (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,72587-15-6, its application will become more common.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 942947-95-7, 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 942947-95-7 as follows.

To a mixture of 5-bromo-4-chloro-3-nitro-pyridin-2-ylamine (0.126 g, 0.50 mmol) and isopropanol (9 ml) was added 2-(piperazin-1-yl)-1-(pyrrolidin-1-yl)ethanone (0.108 g, 0.55 mmol) followed by diisopropylethylamine (0.10 ml, 0.55 mmol). The reaction mixture was heated at 45 C. for 22 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 70% ethyl acetate in dichloromethane and then 90% ethyl acetate in dichloromethane. The title compound was obtained as a yellow solid (0.162 g, 78%); 1H-NMR (500 MHz, DMSO-d6) 1.74 (m, 2H) and 1.85 (m, 2H) (pyrrolidine 3-CH2 and 4-CH2), 2.60 (br s, 4H, piperazine N(CH2)2), 3.04 (br s, 4H, piperazine N(CH2)2), 3.16 (s, 2H, NCH2CO), 3.27 (t, J=6.90 Hz, 2H) and 3.45 (t, J=6.70 Hz, 2H) (pyrrolidine 2-CH2 and 5-CH2), 7.02 (s, 2H, NH2), 8.16 (s, 1H, 6-H);LC (Method B)-MS (ESI, m/z) Rt=1.89 min-413, 415 [(M+H)+, Br isotopic pattern].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,942947-95-7, its application will become more common.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 34552-13-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.34552-13-1, name is 2-Chloro-5-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

Step A: 2,6-Dichloro-5-methylpyridin-3-amine. NCS (32.9 g, 246 mmol) was added in portions to a solution of 2-chloro-5-methylpyridin-3-amine (35.0 g, 245 mmol) and acetonitrile (250 mL). The resulting mixture was heated at 35 C. for 16 hours before cooling to room temperature. The resulting suspension was filtered, and the filtrate concentrated to dryness under reduced pressure. The residue was purified by flash chromatography (eluent:petroleum ether/ethyl acetate; 1:0 to 4:1, gradient elution) to afford the title compound (45 g, 99%). MS (ESI): mass calcd. For C6H6Cl2N2 176.0 m/z found 176.8 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 7.07 (s, 1H), 5.65 (br s, 2H), 2.53 (s, 3H).

Statistics shows that 34552-13-1 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyridin-3-amine.

Reference:
Patent; Janssen Pharmaceutica NV; Barbay, J. Kent; Chai, Wenying; Hirst, Gavin C.; Kreutter, Kevin D.; Kummer, David A.; McClure, Kelly J.; Nishimura, Rachel T.; Shih, Amy Y.; Venable, Jennifer D.; Venkatesan, Hariharan; Wei, Jianmei; (501 pag.)US2020/55874; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16133-25-8, Pyridine-3-sulfonyl chloride, 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, 16133-25-8, blongs to pyridine-derivatives compound. Recommanded Product: 16133-25-8

Reference Example 23; tert-butyl { [5-bromo-l- (pyridin-3-ylsulfonyl) -lH-pyrrol-3- yl]methyl }methylcarbamate; To a suspension of sodium hydride (60percent in oil, 7.4 g) in tetrahydrofuran (300 mL) was added a solution of tert-butyl [ (5-bromo-lH-pyrrol-3-yl) methyl]methylcarbamate (44.5 g) in tetrahydrofuran (60 mL) at 0°C, and 15-crown-5 (40.7 g) and pyridine-3-sulfonyl chloride (30.1 g) were added at the same temperature. The mixture was stirred at room temperature for 30 min, water was added and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixed solvent of diisopropyl ether-hexane=l : 1 to give the title compound as colorless crystals (yield 45.2 g, 68percent) . 1H-NMR (CDCl3) delta: 1.47(9H,s), 2.80 (3H,brs) , 4.18 (2H,brs) ,6.28(lH,brs) , 7.35 (lH,brs) , 7.48-7.52 (IH,m) , 8.18-8.22 (lH,m) , 8.85-8.88 ( IH,m), 9.12-9.13 (IH, m) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16133-25-8, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/108380; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59718-84-2, 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 59718-84-2, name is Methyl 3-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 3-methylpyridine-2-carboxylate (800 mg, 5.29 mmol, 1.00 equiv) and 3-chloroperoxybenzoic acid (1826 mg, 10.58 mmol, 2.00 equiv) in dichloromethane (20 mL) was stirred for 4 hours at 45 C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:3). This resulted in the title compound (850 mg, 96%) as yellow oil. LC-MS (ES, mlz): 168 [M+H]+

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 59718-84-2, Methyl 3-methylpicolinate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89284-61-7, 4-Chloronicotinonitrile, 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, 89284-61-7, blongs to pyridine-derivatives compound. Safety of 4-Chloronicotinonitrile

Step B: Preparation of 4-((lr,4r)-4-(l-(5-(2-Fluoropropan-2-yl)-l,2,4-oxadiazol-3- yl)piperidin-4-yloxy)cyclohexyloxy)nicotinonitrile (Compound 10).Potassium 2-methylpropan-2-olate (0.293 mL, 0.293 mmol) was added to a solution of( 1 r,4r)-4-( 1 -(5-(2-fluoropropan-2-yl)- 1 ,2,4-oxadiazol-3-yl)piperidin-4-yloxy)cyclohexanol (0.08 g, 0.24 mmol) and 4-chloronicotinonitrile (40.6 mg, 0.293 mmol) in THF (2.4 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h and then was diluted with DCM and washed with saturated aqueous NaHC03. The DCM layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica gel, 0-5% MeOH in DCM) and then HPLC to give the title compound (47 mg). LCMS m/z = 430.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.57-1.70 (m, 4H), 1.75-1.84 (m, 8H), 1.87-1.94 (m, 2H), 1.96-2.05 (m, 2H), 2.12-2.21 (m, 2H), 3.22-3.29 (m, 2H), 3.60-3.70 (m, 2H), 3.75-3.81 (m, 2H), 4.73-4.79 (m, 1H), 7.13 (d, J = 4.5 Hz, 1H), 8.71-8.84 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89284-61-7, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert, M.; BUZARD, Daniel, J.; HAN, Sangdon; KIM, Sun, Hee; LEHMANN, Juerg; WO2012/170702; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131748-14-6, Adding some certain compound to certain chemical reactions, such as: 131748-14-6, name is 4-Chloro-(2-trifluoromethyl)pyridine,molecular formula is C6H3ClF3N, 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 131748-14-6.

NaH (60% dispersion in mineral oil, 46 mg, .1.19 mmol) was added portionwise to a stirred solution of l-Boc-4-hydroxypiperidine (CAS: 109384-19-2; 200 mg, 0.99 mmol) in DMF (3 mL) in a sealed tube and under N2 at 0 C. The reaction mixture was stirred at 0 C for 30 min and a solution of 4-chloro-2-(trifluoromethyl)pyridine (CAS: 131748- 14-6; 271 mg, 1.49 mmol) in DMF (2 mL) was added dropwise at 0 C. The reaction mixture was stirred at 60 C for 48 h. The mixture was concentrated in vacuo. The residue was diluted with water and extracted with EtOAc. The organic layer was dried (Na2S04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica, EtOAc in DCM, gradient from 0:100 to 50:50). The desired fractions were collected and concentrated in vacuo to afford intermediate 104 (212 mg, 62%) as colorless oil which solidified to a white solid upon standing

According to the analysis of related databases, 131748-14-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; DELGADO-JIMENEZ, Francisca; CONDE-CEIDE, Susana; VEGA RAMIRO, Juan, Antonio; (245 pag.)WO2019/243530; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58483-95-7 , The common heterocyclic compound, 58483-95-7, name is 5-Amino-2-chloropyridine-4-carboxylic acid, molecular formula is C6H5ClN2O2, 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.

6-Chloro-3H-pyrido[3,4-d]pyrimidin-4-one. A solution of 5-amino-2-chloropyridine-4-carboxylic acid (8.1 g, 4.7 mmol) in formamide (100 mL) is stirred at 140° C. for 12 h. Dilution of the cooled mixture with water gives a precipitate of 6-chloro-3H-pyrido[3,4-d]pyrimidin-4-one (7.3 g, 86percent yield). 1 H NMR (DMSO) delta 12.73 (1H, m), 8.90 (1H, d, J=0.7 Hz), 8.23 (1H, s), 7.97 (1H, d, J=0.7 Hz).

The synthetic route of 58483-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US5654307; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7295-76-3, 3-Methoxypyridine, 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, 7295-76-3, blongs to pyridine-derivatives compound. COA of Formula: C6H7NO

General procedure: [Li(TMP)Zn(tBu)2] 1 was made according to the literature procedure2 on a 0.4 mmol scale in THF solution. To this solution 3-methoxypyridine (0.042 mL, 0.4 mmol) was added and the resultant light orange reaction allowed to stir at room temperature for 2 hours. This solution was then transferred to a THF (1 mL) solution of PdCl2(dppf) (29.3 mg, 10 mol %) and 1-bromo-4-chlorobenzene (76.6 mg, 0.4 mmol) to give a heterogeneous red solution. The reaction mixture was then reacted in the microwave at 100C for 10 minutes. The reaction was then quenched with saturated NH4Cl solution (2 mL) and extracted with DCM (3 x 1 mL). The organic fractions were combined and dried by passing through a phase separator cartridge with a hydrophobic frit and the solvent removed under reduced pressure. The residue was purified by column chromatography using a 4 g C18 silica cartridge and eluent Acetonitrile + 0.1 % formic acid:H2O + 0.1 % formic acid (5:95 to 95:5) to give compound 3b as an off white solid 26.5 mg (30% yield) 1H NMR (400 MHz, CDCl3) delta ppm 3.93 (s, 3H) 7.24 (d, J=4.69 Hz, 1 H) 7.39 – 7.46 (m, 2 H) 7.48 – 7.56 (m, 2 H) 8.33 (d, J=4.49 Hz, 1 H) 8.39 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7295-76-3, its application will become more common.

Reference:
Article; Blair, Victoria L.; Blakemore, David C.; Hay, Duncan; Hevia, Eva; Pryde, David C.; Tetrahedron Letters; vol. 52; 36; (2011); p. 4590 – 4594;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem