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. 59020-10-9, name is 3-(Tributylstannyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

EXAMPLE 64 Ethyl (2S)-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}-2-(3-oxo-2-pyridin-3-yl-spiro[3.5]non-1-en-1-ylamino)propanoate A mixture of the compound of Example 63 (1.0 g, 1.6 mmol), 10% palladium on charcoal (15 mg), triphenylphosphine (100 mg, 0.32 mmol), copper (1) iodide (30 mg, 0.16 mmol), 3-pyridyl tributylstannane (560 mul, 1.7 mmol) in DMF (10 ml) was heated to 100 under a nitrogen atmosphere fro 2 hours. The slvent was removed by evaporation in vacuo and the residue purified by column chromatography (SiO2; 666:333:1 EtOAc:hexane;triethylamine) to give the title compound as a yellow oil (378 mg, 41%). deltaH (DMSO d6) 8.76 (2H, s), 8.60 (1H, m), 8.30 (2H, br. s), 7.94 (1H, d, J 8.0 Hz), 7.54 (2H, m), 7.34 (2H, m), 7.10 (1H, d, J 8.4 Hz), 4.34 (1H, m), 4.24 (2H, q, J 5.3 Hz), 3.25-2.95 (2H, m), 1.86-1.40 (10H, m), 1.26 (3H, t, J 5.3 Hz); m/z (ES+, 70V) 593.0 (MH+).

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, 59020-10-9, 3-(Tributylstannyl)pyridine.

Reference:
Patent; Brand, Stephen; Bailey, Stuart; Brown, Julien A.; Johnson, James A.; Porter, John R.; Head, John C.; US2002/169336; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72617-82-4, 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.72617-82-4, name is 6-(2,2,2-Trifluoroethoxy)pyridin-3-amine, molecular formula is C7H7F3N2O, molecular weight is 192.14, as common compound, the synthetic route is as follows.

Step 3: 8-Hydroxy-2-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-2-aza-spiro[4.5]decan-1-one 6-(2,2,2-Trifluoro-ethoxy)-pyridin-3-ylamine (5.11 g, obtained in example 108, step 2) was added to a solution of 4-hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester (5.10 g, obtained in example 2, step 3) in toluene (160 mL).

Statistics shows that 72617-82-4 is playing an increasingly important role. we look forward to future research findings about 6-(2,2,2-Trifluoroethoxy)pyridin-3-amine.

Reference:
Patent; Ackermann, Jean; Brugger, Stephan; Conte, Aurelia; Hunziker, Daniel; Neidhart, Werner; Nettekoven, Matthias; Schulz-Gasch, Tanja; Wertheimer, Stanley; US2011/92512; (2011); 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. 102645-33-0, name is 2,5-Dichloroisonicotinaldehyde, molecular formula is C6H3Cl2NO, 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. name: 2,5-Dichloroisonicotinaldehyde

Intermediate 9: (2. 5-Dichloro-4-pyridinvl) methanedivl diacetate; Concentrated sulfuric acid (3 drops) was added to a suspension of 2, 5-dichloro-4- pyridinecarbaldehyde (Intermediate 8,4. 0g) in acetic anhydride (25ml) and the mixture was stirred at room temperature for 20h. The acetic anhydride was removed under vacuum to give the title compound as a pale brown oil. LC-MS: Rt 2.94min, MH+ 278

With the rapid development of chemical substances, we look forward to future research findings about 102645-33-0.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/73232; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 153747-97-8, Adding some certain compound to certain chemical reactions, such as: 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate,molecular formula is C14H20BrN3O2, 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 153747-97-8.

To a stirred solution of tert-butyl 4-(5-bromo-2-pyridyl)piperazine-1-carboxylate (3 g, 8.77mmol) in dioxane (30 mL), 4 N HCl in dioxane (10 mL) was added at RT and stirred for 4 h(TLC indicated complete consumption of starting material). EtOAc (50 mL) was added to thereaction mixture, stirred for 30 min., the solid was filtered, washed with ether (20 mL) anddried under reduced pressure to afford 1-(5-bromo-2-pyridyl)piperazine hydrochloride (2.1 g,93%) as an off-white solid. LCMS (ESI+ ): m/z: 242.43 [M+Ht.

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 896722-51-3, 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. 896722-51-3, name is 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

To a solution of 14b (4.50 mmol, 1.22 g) in 30 mL ethanol wasadded 4N NaOH solutions (10 mL). The resulting mixture washeated to reflux for 10 h, cooled down to room temperature andconcentrated under reduced vacuum. Water (30 mL) was added tothe reaction, and the mixturewas extracted with EtOAc (15mL 3).The combined organic phase was dried over anhydride sodiumsulfate and concentrated under reduced vacuum. The residue wasfurther purified by column chromatography on silica gel using PE/EA as eluent to afford product 7o, yield: 70%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,896722-51-3, 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Liu, Bin; Yuan, Xia; Xu, Bo; Zhang, Han; Li, Ridong; Wang, Xin; Ge, Zemei; Li, Runtao; European Journal of Medicinal Chemistry; vol. 170; (2019); p. 1 – 15;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-50-7, 3-Bromo-2-methoxy-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, 15862-50-7, blongs to pyridine-derivatives compound. Formula: C6H5BrN2O3

2nd Step Pd(PPh3)4 (60 mg) and tributyl (1-ethoxyvinyl)tin were added to a DMAc (3 ml) solution containing 3-bromo-2-methoxy-5-nitropyridine (69 mg) obtained in the 1st step, followed by microwave irradiation (Initiator, 180 C., 10 minutes, 2.45 GHz, 0-240 W). Saturated sodium hydrogen carbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 3:7). A light yellow solid of 1-(2-methoxy-5-nitropyridin-3-yl)ethanone (72 mg) was thus obtained. MS (ESI m/z): 197 (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,15862-50-7, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; FUJIWARA, Hideyasu; MIZUMOTO, Shinsuke; KUBO, Yohei; NAKATA, Hiyoku; HAGIWARA, Shinji; BABA, Yasutaka; TAMURA, Takashi; KUNIYOSHI, Hidenobu; MASHIKO, Tomoyuki; YAMAMOTO, Mari; US2014/309225; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 824-51-1 , The common heterocyclic compound, 824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H8N2, 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 6-methyl-1H-pyrrolo[2,3-b]pyri- dine (500 mg) in dichioroethane (6 mE) were added aluminum chloride (1.09 g) and acetyl chloride (0.40 mE), and then the mixture was stirred at room temperature for 1 .5 hours. The reaction solution was poured into aqueous saturated sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with isopropyl ether to give 1 -(6-methyl-1H-pyrrolo[2,3-b]pyri- din-3-yl)ethanone [REx(8-i)] (481 mg) as a yellow powder. APCI-MS mlz: 175 [M+H].

The synthetic route of 824-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceuticals Holding CO., LTD.; MITSUBISHI TANABE PHARMA CORPORATION; Iijima, Toru; Takahashi, Yoichi; Hirai, Miki; Sugama, Hiroshi; Togashi, Yuko; Shen, Jingkang; Xia, Guangxin; Wan, Huixin; US2015/232459; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60010-03-9, 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.60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine, molecular formula is C6H4Cl2N2O2, molecular weight is 207.01, as common compound, the synthetic route is as follows.

6-Chloro-2-((f?)-3-fluoro-pyrrolidin-1 -yl)-4-methyl-3-nitro-pyhdine (Intermediate compound)To a solution of 2,6-dichloro-4-methyl-3-nitropyhdine (6.5g; 31.4 mmol) and TEA (1 Og; 3eq) in acetonitrile (200ml) was added (f?)-(-)-3-fluoropyrrolidine hydrochloride (4.75g; 1.2eq). The mixture was stirred for 4h at rt, after which the reaction mixture was quenched with sat NaHCOs(aq) (300ml), diluted with water and and EtOAc. The layers were separeted and the waterlayer was extracted with EtOAc (3x15OmL) untill no UV(254nm) active material was extracted). The com- bined organic layers were washed with brine and dried over Na2SO4(s). Filtration and in vacuo concentration resulted in a quantitative yield 8.36g of the title compound as a yellow/orange oil.

Statistics shows that 60010-03-9 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloro-4-methyl-3-nitropyridine.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; MATTSSON, Cecilia; SOTT, Richard; STRØBAeK, Dorte; WO2010/122064; (2010); 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.89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, molecular weight is 221, as common compound, the synthetic route is as follows.name: 3-Iodopyridin-4-ol

General procedure: In a pressure tube, a suspension of 5% Pd/C (5 mol%), 2-bromo-3-hydroxypyridine (0.5 mmol), LiCl (0.5 mmol),cesium carbonate (1 mmol), and terminal alkyne (1.0 mmol)in DMF (3 mL) was stirred for designated period at 150 C.The reaction mixture was filtered, and neutralized with saturatedNH4Cl solution, followed by extraction with ethyl acetate.The crude product was purified by columnchromatography with the use of hexane and ethyl acetate aseluents.The following compounds were prepared with abovedescribed general procedure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89282-03-1, 3-Iodopyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Article; Park, Hee Jung; Kim, Ji-Eun; Yum, Eul Kgun; Kim, Young Hoon; Han, And Chang-Woo; Bulletin of the Korean Chemical Society; vol. 36; 1; (2015); p. 211 – 218;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 108118-69-0, 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. 108118-69-0, name is 2,6-Difluoropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 4-(tert~butoxycarbonyl-methyl-amino)-benzoic acid (70 mg, 0.28 mmol) in CHiCi2 (2 mL) was added l-chloro-N,N-2-trimethylpropenylamine (98 muL, 0.74 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (2 mL) before 2,6~difluoro-rhoyridin-3-ylamine (30 mg, 0.23 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue to which was added DMF (2 mL) and K2CO3 (64 mg, 0.46 mmol). The resulting mixture was heated by microwave to 150 0C for 10 min, after which the resulting mixture was filtered, concentrated and purified by silica gel flash chromatography (0 to 100% EtOAc in hexanes) to afford [4-(5-fluoro-oxazolo[5s4-6]pyridine-2- yl)-phenyl]-methyl-amine (50 mg, 0.21 mmol, 89%). ES MS (M+H+) – 244; Eta NMR (300 MHz, DMSO-d6): delta 8.24 (t, J – 7.7 Hz, 1 H); 7.89 (d, J = 8.4 Hz, 2 H); 7.18 (d, J = 8.4 Hz, 1 H); 6.68 (d, J = 8.5 Hz, 3 H); 2.76 (s, 3 H); HRMS m/z 244.0883 (C13H10FN3O + H+ requires 244.0881).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108118-69-0, 2,6-Difluoropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/155017; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem