Category: pyridine-derivatives

Application of 1214334-70-9, 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. A new synthetic method of this compound is introduced below.

[0436] To a stirred solution of 5-bromo-6-methoxypicolinic acid (350 mg, 1 mmol) in CH2C12 (2 mL) under an argon atmosphere were added oxalyl chloride (347 mg, 2 mmol) and DMF (catalytic amount) at 0 C. The reaction mixture was stirred at room temperature for 2 h. After consumption of acid (by TLC), the volatiles were evaporated in vacuo to give 5- bromo-6-methoxypicolinoyl chloride.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 175205-82-0, 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 175205-82-0 as follows.

2-Bromo-3-(trifluoromethyl)pyridine (1 .5 g, 6.63 mmol) is added to a solution of example 16a (500 mg, 2.21 mmol) in TEA (3.5 mL, 25.25 mmol) and dry ACN (14 mL) at rt. Then Copper (I) Iodide (84 mg, 0.442 mmol) and dichlorobis(triphenylphosphine)palladium(II) (155 mg, 0.221 mmol) are added and stirring is continued overnight. Solvent is evaporated under reduced pressure and the crude is purified byflash chromatography (eluent 0-40% EtOAc/cyclohexane) to furnish the title compound (800 mg, 99%).U PLC-MS (Method 2): R = 1 .23 mm MS (ESI pos): mlz = 363 (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,175205-82-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 23056-33-9, 2-Chloro-4-methyl-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, Recommanded Product: 23056-33-9, blongs to pyridine-derivatives compound. Recommanded Product: 23056-33-9

1A. 2-Chloro-5-nitro-isonicotinic acid methyl ester To a solution of 2-chloro-4-methyl-5-nitropyridine (Aldrich Chemical Co.) (5.0 g, 29.0 mmol) in concentrated sulfuric acid (60 mL) with stirring at 0 C was added a solution of sodium dichromate dihydrate (14.3 g, 1.65 eq) in concentrated sulfuric acid (100 mL) at a rate which kept the internal temperature less than 10 C. After addition was complete, the reaction mixture was stirred from 0 C. to room temperature over 6 hours. By TLC, the reaction was not complete, so additional sodium dichromate dihydrate (8.4 g, 1 eq) was added directly to the solution at 0 C. The resulting solution was stirred from 0 C. to room temperature overnight. The reaction was complete by TLC the next morning, and it was poured into a mixture of ice (1 L) and EtOAc (900 mL). The resulting mixture was stirred for about 10 minutes and then the layers were separated. The organic layer was washed with brine (2x 600 mL), and the EtOAc layer was dried over magnesium sulfate and filtered. With stirring at room temperature, trimethylsilyl diazomethathane (2.0M in hexanes, 15 mL) was added to the EtOAc filtrate. The resulting mixture was stirred at room temperature for 30 min. By TLC, there was no acid remaining, and then MeOH (150 mL) was added and the solution stirred for 30 minutes. The solution was concentrated and then EtOAc (700 mL) was added to the residue which was dried over magnesium sulfate, filtered, concentrated and pumped to give the title compound (1A) as an off-white powder (5.79 g, M+=216, M.P.=60.5-64.1C.).

The synthetic route of 23056-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dewdney, Nolan James; Goldstein, David Michael; US2004/209903; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22245-83-6, 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. 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol, molecular formula is C6H4F3NO, 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 an ice-cooled solution of 3-(trifluoromethyl)pyridin-2-ol (5 g, 30.7 mmol) in H2SO4 (30 mL, 563 mmol) was added nitric acid (1.507 mL, 33.7 mmol) dropwise. After 30 min, the ice bath was removed and the reaction mixture was stirred at 25 C for 16 h. The reaction mixture was warmed to 60 C for 5 h, cooled, and added to 150 g of ice. The resulting precipitate was collected by filtration, rinsed with additional H20, and air-dried to afford the first batch of product. Another crop of product was obtained after evaporating the mother liquor to less than 100 mL, cooling on an ice bath, and adding NaOH to adjust to pH 8. The mixture was extracted by EA (100 mL). The organic layer was dried and concentrated to give the product, which was combined with the first batch to yield a yellow solid of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (5 g, 24.03 mmol, 78.0% yield): NMR (400 MHz, CD3OD) delta 8.85 (d, J= 3.2 Hz, 1H), 8.58 (d, J= 2.8 Hz, 1H).

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 22245-83-6, 3-(Trifluoromethyl)pyridin-2-ol.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EIDAM, Hilary Schenck; DEMARTINO, Michael P.; GONG, Zhen; GUAN, Amy Huiping; RAHA, Kaushik; WU, Chengde; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; CHEUNG, Mui; WO2014/141187; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 695-34-1, 4-Methylpyridin-2-amine, 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: C6H8N2, blongs to pyridine-derivatives compound. COA of Formula: C6H8N2

In a nitrogen atmosphere, 1.08 g of 2-amino-4-methylpyridine was dissolved in 75 mL of tetrahydrofuran, and tetrahydrofuran (75 mL) solution of 3.20 g of pyridinium hydrobromide perbromide was dropwise added thereto at room temperature, over 1.5 hours. After the addition, this was stirred at room temperature for 40 minutes, and 100 mL of aqueous saturated sodium sulfite solution was added to the reaction mixture. This was extracted with ethyl acetate, and the ethyl acetate layer was dried with magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate = 4/1 to ethyl acetate) to obtain 1.00 g of the entitled compound as a white solid.

The synthetic route of 695-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1726590; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 160599-70-2, 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. 160599-70-2, name is 2,5-Dibromo-3-chloropyridine, molecular formula is C5H2Br2ClN, 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.

A 100-mL pressure vessel was charged with 4,4,5, 5-tetramethyl-2-(4- (phenylsulfonyl)phenyl)-l,3,2-dioxaborolane (6.34 g, 18.43 mmol), 2,5-dibromo- 3-chloropyridine (5.00 g, 18.43 mmol, Sigma-Aldrich, St. Louis, MO), potassium carbonate (7.64 g, 55.3 mmol), tetrakis(triphenylphosphine)palladium (1.06 g, 0.92 mmol, Strem Chemical Inc, Newburyport, MA), 20 mL of 1,2- dimethoxy ethane, and 4 mL of water. The vessel was sealed and the reaction mixture was heated at 100 C for 8 h. After cooling to room temperature, the mixture was diluted with EtOAc (30 mL) and water. The layers were separated and the organic phase was dried (MgS04), filtered, and concentrated under a vacuum to give an oil. Purification via column chromatography (40 g of silica gel, 0 to 50% EtOAc in hexanes) produced 5-bromo-3-chloro-2-(4- (phenylsulfonyl)phenyl)pyridine (2.56 g) as a tan solid.

According to the analysis of related databases, 160599-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1173081-96-3 , The common heterocyclic compound, 1173081-96-3, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride, molecular formula is C8H13ClN2O, 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 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid (1.06 g, 2.25 mmol) in DMSO (5.8 mL) at rt was added triethylamine (0.90 mL, 6.44 mmol) and (4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methanaminium chloride (0.405 g, 2.15 mmol). The clear solution become heterogenous. Then HOBT (0.493 g, 3.22 mmol) and EDC (0.617 g, 3.22 mmol) were added and the resulting reaction mixture was stirred at rt overnight. The reaction was quenched with water (80 mL) and the slurry was stirred for 1 h at rt. The slurry was filtrated and the cake was washed with water (2*20 mL). The collected solid was dried under vacuum to give the titled compound (1.27 g, 98% yield). 1H-NMR (500 MHz, CD3OD) 8 ppm; 7.22 (s, 1H), 7.08 (d, J=1.0 Hz 1H), 6.11 (s, 1H), 4.45 (s, 2H), 3.92 (brd, J=10.8 Hz, 2H), 3.78 (dd, J=4.4, 5.4 Hz, 1H), 3.75 (dd, J=4.4, 5.4 Hz, 1H), 3.36 (t, J=11.7 Hz, 2H), 3.21 (br t, J=8.3 Hz, 2H), 3.07 (q, J=7.3 Hz, 2H), 3.01 (dddd, J=3.9, 3.9, 11.3, 11.3 Hz, 1H), 2.84 (dddd, J=3.4, 3.4. 3.9, 3.9 Hz, 1H), 2.38 (s, 3H), 2.28 (s, 3H), 2.25 (s, 3H), 1.88 (m, 2H), 1.70 ((brd, J=12.2 Hz, 2H), 1.60 (m, 4H), 1.47 (s, 9H), 0.87 (t, J=7.3 Hz, 3H); MS (ESI) [M+H]+605.6.

The synthetic route of 1173081-96-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kuntz, Kevin Wayne; Campbell, John Emmerson; Seki, Masashi; US2014/107122; (2014); 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.16063-69-7, name is 2,4,6-Trichloropyridine, molecular formula is C5H2Cl3N, molecular weight is 182.44, as common compound, the synthetic route is as follows.Recommanded Product: 2,4,6-Trichloropyridine

To a 15 mL vial equiped with a stir bar was added 2,4,6-trichloropyridine (365 mg, 2.00 mmol) and Pd(dppf)Cl2 (146 mg, 0.200 mmol). The vial was sealed with a septum screwcap and then was placed under N2 atmosphere. To the vial was added thiazol-2-ylzinc(II) bromide in THF (10.0 mL, 5.00 mmol). The vial was placed in a 60 C heating block with stirring for 16 h. The reaction mixture was cooled to room temperature, and then was transfered to a 125 mL separatory funnel where it was diluted with Et20 (50 mL) and water (50 mL). The mixture was filtered to remove a significant amount of a yellow-white precipitate and the filtrate was returned to the separatory funnel. The phases were isolated and the aqueous phase was extracted with EtOAc (25 mL). The combined organics were washed with brine (50 mL); dried over MgS04; filtered; then concentrated in vacuo to afford a pale yellow solid which was subjected to silica gel chromatography (CH2Ci2:MeOH, 100:0 to 90: 10) to afford 2,2′-(4-chloropyridine-2,6-diyl)dithiazole as a white solid (294 mg, 53%). 1H-NMR (400MHz, CDC13) delta 8.23 (s, 2H), 7.97 (d, J=3.0 Hz, 2H), 7.53 (d, J=3.3 Hz, 2H); MS: MS m/z 280.0 (M++l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16063-69-7, 2,4,6-Trichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILLIS, Eric P.; BOWSHER, Michael S.; SCOLA, Paul Michael; WO2014/71007; (2014); 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. 183610-70-0, name is 2-Amino-3-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, 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. SDS of cas: 183610-70-0

In a 7 ml screw cap vial 1,1-dimethylethyl (2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.10 g, 0.31 mmol), DMF (1 ml) and 3-(trifluoromethyl)-2-pyridinamine (0.076 g, 0.47 mmol) were added and the resulting mixture stirred at 80 C. for 13 h. The mixture was eluted through a SCX column. Collected fractions gave 0.15 g of a crude containing the title compound D7, the corresponding free amine and some residual 3-(trifluoromethyl)-2-pyridinamine. The material was used in the next step without further purification. HPLC (walk-up): rt=3.79 min. MS: (ES/+) m/z: 384 (M+1). C19H24F3N3O2 requires 383.

With the rapid development of chemical substances, we look forward to future research findings about 183610-70-0.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); 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. 72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloromethyl-3,4-dimethoxypyridinium chloride

10% NaOH solution (42.5 gm in 425 ml of water) is added drop wise to a solution of 5-(difluoromethoxy)-2-mercapto benzimidazole (100.0 gm; 0.462 moles) in methanol(350.0 ml) at 10-150C. To the above solution a clear solution of 2-chloro-3, 4-dimethoxy pyridine hydrochloride (105.5 gm.0.473 moles in 525 ml of methanol) was added at 10-150C. The reaction mass was maintained at 10-15C for 30 minutes. The temperature of the reaction mass was slowly raised to 2O0C. The reaction mass was maintained at 20-25 C for 2 hours. Further the temperature was raised to 400C and maintained at 400C. Completion of the reaction is monitored by TLC. After completion of the reaction methanol is evaporated under reduced pressure to get a residue. Chilled water (600 ml) was added to the residue and the reaction mass was extracted with methylene chloride (600 ml, 300 ml x 2). The organic layers were separated and evaporated under reduced pressure to obtain a residue. Isopropyl alcohol (50 ml) and hexane (600 ml) were added to the reaction mass. The reaction mass was cooled to 0-50C and maintained at 0-5C for 30 minutes. The reaction mass was filtered at 0-5C and washed with chilled hexane (100 ml). The solids were dried under vacuum at 4O0C; Dry wt-162 gm (Yield=95.3%); HPLC Purity=99.21% w/w.; Melting range=l 15-1170C (Lit.7mp-H5-1 18C); MS (ESI); 368.0(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, 72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride.

Reference:
Patent; MACLEODS PHARMACEUTICALS LIMITED; WO2009/66317; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem