Category: pyridine-derivatives

Related Products of 59782-86-4, 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. 59782-86-4, name is 2-Chloro-5-iodonicotinic acid, molecular formula is C6H3ClINO2, 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.

To a solution of 4-fluorophenol (224 mg, 2.0 mmol) in DMF (5.0 mL) was added sodium hydride (48 mg, 2.0 mmol) at room temperature. After stirring for 10 min, methyl 2-chloro-5-iodonicotinate (J. Org. Chem. 1989, 54, 3618-3624, 594 mg, 2.0 mmol) was added to the reaction mixture. The reaction mixture was stirred under reflux for 16 h. Then the reaction mixture was poured into water (50 mL) and extracted with ether (50 mL x 3). The combined organic extracts were washed with brIne (50 m(at)-) and dr*(at)–d, (sod.uTY: s.1l(at)a(at)e). After removal o4 the 3ci’.3(at)f:(at) t’e (at)3(at):::(at)(at) <";zs ;'.(at)-Z?"(at)'(at)(at)3(at) hy7 '(at):(at):1B(at)(at) xt(at)l:r- :-;(at)(at)(at)(at)(at).(at)5..t:;,?"£;:(at).;/ 8(at)(at)(at)0E. £ ,q], L .-.."I.: -'-(at)2(at)::'(at)0/;:/::*-(at),(at)(at) ::_=J'(at)(at)'(at)(at)- (J.>,’. ] .:: ilf=No.= (at):<.No...---'(at) (I? lflXJ i:.: ..:.:,i .::":.1 compound: (at)H-NMR (CDCl3) No. 8.51 (1 H, d, J=2.3 Hz), 8.41 (1 H, s), 7.09 (4H, d, J=6.2 Hz), 3.95 (3H, s) ; MS (ESI) m/z 374 (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 59782-86-4, 2-Chloro-5-iodonicotinic acid. Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/102389; (2005); A2;,
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. 59020-10-9, name is 3-(Tributylstannyl)pyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

A mixture of 8-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (100 mg) (as prepared in Example 4), 3-(tri-n-butylstannyl)pyridine (442 mg) and DMF (5 ml) was degassed with a stream of N2 for 0.5 h. Bis(triphenylphosphine)palladium(II) chloride (5 mg) was added and the reaction heated to 100 C. for 2 h. The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica, eluting with 2.5% MeOH/CH2Cl2 to give the title compound (75 mg, 64%). 1H NMR (400 MHz, CDCl3) ? 8.66 (1H, t, J=3.3 Hz), 8.23 (1H, d, J=1.4 Hz), 7.95-7.92 (1H, m), 7.63 (1H, dd, J=8.0, 1.7 Hz), 7.57-7.54 (2H, m), 7.49-7.38 (5H, m), 4.07 (2H, s), 3.97 (2H, s), 2.73 IS (3H, s), m/z (ES+) 392 (M+H)+.

The synthetic route of 59020-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boase, Amanda Louise; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; US2004/58970; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.72141-44-7, name is 4-Chloro-2-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.5709, as common compound, the synthetic route is as follows.Formula: C6H6ClNO

To a solution of LDA (1.0 M solution in hexane) (29.3 mL, 29.3 mmol) in THF (45 mL) was added a solution of 4-chloro-2-methoxypyridine (3.5 g, 24.38 mmol) in THF (8 mL) dropwise at -78 C. The reaction mixture turned into light yellow solution and was stirred at-78 C for 1 h, then DMF (3.78 mL, 48.8 mmol) was added dropwise. The reaction mixture was stirred at -78 C for lh. The reaction mixture was quenched with saturated NH4C1 solution at -78 C and the resulting mixture was stirred for 10 min and warmed up to rt. The resulting mixture was mixed with saturated NaHC03 solution and ethyl acetate. The organic layer was separated and washed with saturated NaHC03 solution, dried over MgS04. The filtrate was concentrated in vacuo. The residue was dissolved in DCM, purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give Intermediate 24A (white solid, 2.6 g, 15.15 mmol, 60% yield). LC-MS Anal. Calc’d for CvHeClNC 171.01, found [M+H] 172.1. Tr = 0.71 min (Method A). NMR (499MHz, chloroform-d) delta 10.47 (s, 1H), 8.20 (d, J=5.5 Hz, 1H), 7.01 (d, J=5.5 Hz, 1H), 4.08 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72141-44-7, 4-Chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 88312-64-5, 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 88312-64-5 as follows.

Preparation Example A+-9. 2-Amino-5-nitro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide 2-Amino-5-nitro-nicotinic acid methyl ester (48.4mg, 0.245mmol) described in Preparation Example A-3 and lithium hydroxide monohydrate (10.3mg, 0.245mmol) were dissolved in a solvent mixture of tetrahydrofuran (1mL), methanol (0.1mL) and water (0.1mL), and the solution was stirred for 17 hours at room temperature. The solvent was evaporated in vacuo, and 2-amino-5-nitro-nicotinic acid was obtained as a lithium salt. Then, the resulting lithium salt of 2-amino-5-nitro-nicotinic acid, C-(5-phenoxy-thiophen-2-yl)-methylamine (60mg, 0.29mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (162mg, 0.367mmol) and triethylamine (103mul, 0.735mmol) were dissolved in N,N-dimethylformamide (2.0mL), and the solution was stirred for 6 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic layer was washed with water and brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1), and the title compound (87mg,0.24mmol,96%) was obtained as a pale yellow solid. 1H-NMR Spectrum (DMSO-d6) delta (ppm) : 4.49 (2H, d, J=5.5Hz), 6.50 (1 H, d, J=3.7Hz), 6.80 (1H, d, J=3.1Hz), 7.08 (2H, d, J=7.7Hz), 7.13 (1H, t, J=7.5Hz), 7.37 (2H, t, J=7.5Hz), 8.76 (1 H, d, J=2.2Hz), 8.96 (1 H, d, J=1.7Hz), 9.51 (1 H, t, J=5.5Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,88312-64-5, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-18-9, 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. 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, 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.

6-Bromo-3-(ethylsulphanyl)pyridine-2-carboxylic acid (3 g, 11.5 mmol) was dissolved in 60 ml of dichloromethane and cooled to 0 C. With stirring, oxalyl chloride (14.5 g, 115 mmol) and one drop of dimethylformamide were added, then the mixture was stirred at room temperature for 30 min. After removing the solvent, the crude product 6-bromo-3-(ethylsulphanyl)pyridine-2-carbonyl chloride was further reacted directly. 2-Chloro-5-(trifluoromethyl)pyridin-3-amine (1.05 g, 5.38 mmol) was added at 0 C. to a suspension of sodium hydride (60% in mineral oil, 258 mg, 6.46 mmol) in tetrahydrofuran. The mixture was stirred for 30 min, then 6-bromo-3-(ethylsulphanyl)pyridine-2-carbonyl chloride (3 g, 10.75 mmol) was added in portions. After stirring for 12 h, the reaction was ended by adding 10 ml of ice-water. The product was isolated in the form of a precipitate by filtration. log P (neutral): 5.27; MH+: 442; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 10.57 (s, 1H); 8.91 (s, 1H), 8.70 (s, 1H), 7.95-7.87 (m, 2H), 3.05-3.00 (m, 2H), 1.30-1.27 (m, 3H).

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 72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHSAFT; FISCHER, RUEDIGER; WILCKE, DAVID; KAUSCH-BUSIES, NINA; HAGER, DOMINIK; ILG, KERSTIN; HOFFMEISTER, LAURA; WILLOT, MATTHIEU; PORTZ, DANIELA; GOERGENS, ULRICH; TURBERG, ANDREAS; (161 pag.)US2018/271099; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1452-94-4, 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 1452-94-4, name is Ethyl 2-chloronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

To ethyl 2-chloronicotinate (15.0 g, 81 mmol) in anhydrous N, N-dimethylacetamide (75 ml) was added zinc cyanide (5.71 g, 48.6 mmol), Pd2 (dba) 3 (742 mg, 0.81 mmol), zinc (636 mg, 9.72 mmol), and 1, 1’BIS (diphenylphosphino) ferrocene (898 mg, 1.62 mmol), and the resulting mixture heated at 120 C for 1 hour. The mixture was cooled to room temperature and partitioned between water (300 ml) and diethyl ether (150 ml), the mixture was filtered through Celiez and the phases separated. The aqueous phase was further extracted with diethyl ether (2 x 100 ml), the combined diethyl ether layers washed with saturated NACI, dried over NA2SO4, FILTERED and evaporated to give the title compound (14.26 g, 100%).

According to the analysis of related databases, 1452-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Limited; WO2004/46133; (2004); 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. 34206-49-0, name is 5-Bromopyridine-2,3-diol, the common compound, a new synthetic route is introduced below. COA of Formula: C5H4BrNO2

To a solution of 5-bromopyridine-2,3-diol (10 g, 53.19 mmol, 1 eq.) in DMF (250 mL) atroom temperature was added K2C03 (21 g, 159.57 mmol, 3 eq.) followed by 1,2-dibromoethane(5.5 mL, 63.82 mmol, 1.2 eq.) dropwise. The resulting mixture was stirred at 100C overnight.Progress of reaction was monitored by TLC. After the completion, reaction mixture was cooledto room temperature, diluted with ice cold water (300 mL) and extracted with DCM (3 x300 mL).Combined organic layer was washed with brine and dried over anhydrous sodium sulphate.Removal of solvent under reduced pressure afforded crude was purified by Combi-Flash on silica gel using methanol-dichloromethane (0-50 %) as eluents to afford 7-bromo-2,3-dihydro- [1,4]dioxino[2,3-b]pyridine (2.9 g, 25.26%).LCMS: 215 [M+1]

The synthetic route of 34206-49-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURANSA INC.; PROTTER, Andrew, Asher; GREEN, Michael, John; CHANG, Hak, Jin; PHAM, Son, Minh; CHAKRAVARTY, Sarvajit; LUEDTKE, Gregory, R.; (254 pag.)WO2019/103897; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256805-54-5, 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. 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.

Trimethylaluminum (7.6 mL, 2.0 M in toluene, 15 mmol) was added slowly to a 0 C. mixture of 6-chloro-4-methoxypyridin-3-amine (2.4 g, 15 mmol) and propionitrile (1.16 mL, 16.1 mmol). The flask was removed from the ice bath, allowed to warm to rt over 5 min, then was stirred at 105 C. for 17 hours. The mixture was cooled to 0 C. and THF (15 mL) was added very slowly followed by water (1 mL), 15 wt % aqueous NaOH (1 mL) and water (3 mL), stirring for 10 min after each addition. The resulting mixture was allowed to warm to rt over 30 min with stirring, then Celite was added, and the mixture stirred an additional 30 min. The mixture was then filtered through Celite with THF and concentrated. The residue was diluted with water and the pH adjusted to pH 1-2 by the addition of 1 N aqueous HCl. The solution was then washed twice with EtOAc and the aqueous layer pH adjusted to pH 10-11 by the addition of 1 N aqueous NaOH. The aqueous solution was then extracted four times with DCM, the organic layers combined, dried with anhydrous Na2SO4, filtered and concentrated to provide the title compound, which was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Kummer, David A.; Nishimura, Rachel T.; Tanis, Virginia M.; Woods, Craig R.; Fourie, Anne M.; Xue, Xiaohua; (120 pag.)US2019/382354; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131747-62-1, 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. A new synthetic method of this compound is introduced below.

25 mL of anhydrous THF was placed under nitrogen and cooled to -78 C. 2.2 ml (5.5 mmol) of a 2.5 M solution of n-butyl lithium in hexanes were added. To the resulting solution was slowly added 0.7 mL (1.4 g, 5.8 mmol) of 1,3-dibromobenzene. Upon complete addition the resulting solution was stirred at -78 C. for 90 min. 1.00 g (5.71 mmol) of 3-trifluoromethyl-pyridine-2-carbaldehyde was added rapidly. The dark solution was warmed to -20 C. and stirred for 20 min at that temperature. The resulting mixture was distributed between 10% aqueous citric acid and dichloromethane. The phases were separated and the aqueous layer extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and the solvent completely evaporated. The resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 1.053 g (3.171 mmol, 58%) of (3-bromo-phenyl)-(3-trifluoromethyl-pyridin-2-yl)-methanol as a yellow oil. 1H NMR (500 MHz, DMSO-d6) delta 8.84 (m, 1H), 8.18 (dd, 1H), 7.63 (m, 1H), 7.53 (dd, 1H), 7.42 (m, 1H), 7.26-7.24 (m, 2H), 6.31 (d, 1H), 6.02 (d, 1H),; MS: m/z 332.0+334.0 (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,131747-62-1, its application will become more common.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2008/261921; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 800401-70-1 ,Some common heterocyclic compound, 800401-70-1, molecular formula is C10H9BrN2O2, 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.

PdCl2 (PPh3) 2 (0.026g, 0.037mmol) and Cu (I) I (0.007g, 0. 037MMOL) were added sequentially to 5-BROMO-LH-PYRROLO [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 26, 0. 100G, 0.370mmol) under an argon atmosphere. 1,4-Dioxane (7mL, anhydrous) followed by DIISOPROPYLAMINE (0.063mL, 0. 45MMOL) were added and the stirred mixture was purged with argon for 5min. Trimethylsilylacetylene (0.064mL, 0. 45MMOL) was added dropwise and the resulting mixture stirred at rt for 24h. The reaction mixture was partitioned between water (50ML) and ethyl acetate (LOOML) and the layers separated. The aqueous phase was extracted with ethyl acetate (3X30ML). The combined organics were washed with brine (50ML), dried (MGS04), filtered and concentrated in vacuo. The residue was dissolved in the minimum amount of dichloromethane and loaded onto a silica column. Purification via flash column chromatography (SI02, dichloromethane then 25% ethyl acetate/ isohexane) gave a pale yellow solid. 8H (CDCl3): 0.28 (9H, s), 1.43 (3H, t), 4.45 (2H, q), 7. 18 (1H, s), 7.83 (1H, s), 8.86 (1H, s), 9.21 (1H, br s).

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. 800401-70-1, Ethyl 5-bromo-1H-pyrrolo-[2,3-c]-pyridine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem