Pyridine-derivatives

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. 884495-22-1, name is 5-Bromo-2-fluoropyridin-3-amine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

2-Fluoro-5-morpholinopyridin-3-amine A stirred mixture of 3-amino-5-bromo-2-fluoropyridine (0.96 g, 5.02 mmol), L-proline (0.12 g, 1.01 mmol), potassium carbonate (1.39 g, 10.1 mmol), copper(I) iodide (0.096 g, 0.50 mmol), and morpholine (1.31 mL, 15.04 mmol) in dry DMSO (3.0 mL) was purged three times with argon and placed under vacuum three times, then the mixture was heated to 90 C. After 21.5 h, the reaction was cooled to rt, then treated with water. After extracting twice with EtOAc, the organics were combined and dried over anhydrous sodium sulfate. After filtration and concentration the residue was purified on basic alumina (10-50% EtOAc in hexanes) to afford a white solid as 2-fluoro-5-morpholinopyridin-3-amine. 1H NMR (400 MHz, DMSO-d6) delta ppm 6.96 (1H, t, J=2.6 Hz), 6.75 (1H, dd, J=9.6, 2.7 Hz), 5.25 (2H, br. s.), 3.80 (4H, m), 3.08 (4H, m). Mass Spectrum ESI (pos.) m/e: 198.1 (M+H)+.

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Reference:
Patent; AMGEN INC.; US2010/331293; (2010); 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. 1211534-27-8, name is 5-Fluoro-2-methoxy-3-nitropyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Fluoro-2-methoxy-3-nitropyridine

c) 5-Fluoro-2-methoxypyridin-3-amine 10% Palladium on carbon (0.300 g) was added to a solution of 5-fluoro-2-methoxy-3-nitropyridine (Preparation 5b, 0.300 g, 1.74 mmol) in ethanol (15 mL) and the reaction mixture was stirred at ambient temperature under a hydrogen atmosphere. After 5 hours, the mixture was then filtered through Celite and the filter cake was washed with ethanol. The combined filtrate and washings were concentrated to give the title compound (0.220 g, 89%) as a brown solid. LRMS (m/z): 143 (M+1)+. 1H NMR delta (300 MHz, CDCl3): 3.96 (s, 3H), 6.67 (dd, 1H), 7.39 (d, 1H).

The synthetic route of 1211534-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; EP2527344; (2012); 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. 13466-43-8, name is 3-Bromopyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-Bromopyridin-2(1H)-one

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.

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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;,
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Related Products of 27257-15-4 , The common heterocyclic compound, 27257-15-4, name is 1-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.

General procedure: POCl3 (5.87 ml, 63.0 mmol) was added dropwise to DMF (45 ml) at 0 C, and the mixture was stirred for 20 min at same temperature. A solution of 6-fluoro-1-methylindole (6.71 g, 45.0 mmol) in DMF (45 ml) was added slowly to the mixture at 0 C. After being stirred at room temperature for 1.5 h, the reaction mixture was poured into ice, and the resulting mixture was neutralized with 1 N NaOH and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, and concentrated to dryness. The residue was purified by column chromatography on silica gel with EtOAc as eluent to give the title compound (4.18 g, 52%) as a colorless solid.

The synthetic route of 27257-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Setoguchi, Masaki; Iimura, Shin; Sugimoto, Yuuichi; Yoneda, Yoshiyuki; Chiba, Jun; Watanabe, Toshiyuki; Muro, Fumihito; Iigo, Yutaka; Takayama, Gensuke; Yokoyama, Mika; Taira, Tomoe; Aonuma, Misato; Takashi, Tohru; Nakayama, Atsushi; MacHinaga, Nobuo; Bioorganic and Medicinal Chemistry; vol. 20; 3; (2012); p. 1201 – 1212;,
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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. 1187236-18-5, name is Ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate

To a suspension of ethyl 7-bromoimidazo[l,2-a]pyridine-2-carboxylate (3.50 g, 13.0 mmol) in anhydrous DCM (80 mL) was added diisobutyl aluminum hydride (18.50 mL, 18.50 mmol, 1.0 M) at -78 C under N2 atmosphere. The mixture was stirred at -78 C overnight and then moved to 0 C, and quenched with water (0.75 mL), 15% NaOH aqueous solution (0.75 mL) and another water (2 mL) successively. The resulting mixture was stirred at rt for 15 min. To the mixture were added Et20 (50 mL), EtOAc (50 mL) and hydrous Mg2S04 (20 g), stirred for 15 min, filtered. The filter cake was washed with EtOAc (200 mL), the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/10 to 1/5) to afford the title compound as a light-yellow solid (1.50 g, 51%).MS (ESI, pos. ion) m/z: 225.0 [M+H]+;1H NMR (400 MHz, CDCl3) d (ppm): 10.14 (s, 1H), 8.13 (s, 1H), 8.04 (d, J= 7.2 Hz, 1H), 7.89 (s, 1H), 7.02 (dd, j= 7.2, 1.7 Hz, 1H).

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Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17228-64-7, 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.17228-64-7, name is 2-Chloro-6-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.

To a stirred solution of 9(7.00 g, 48.8 mmol) in CH3CN (25 mL) was added NBS (13.0 g, 73.1 mmol) at room temperature. The resulting mixture was refluxed for 24 h. Then the reaction was quenched with saturated aqueous Na2S2O3and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, n-hexane-EtOAc=98 : 2) to afford methoxypyridine 31(6.83 g, 63%) as a colorless solid.31: mp 64-65C; IR (film, cm-1): 1584, 1551, 1466, 1408, 1344, 1306, 1256, 1155, 1121, 1022, 1009; 1H-NMR (CDCl3, 500 MHz) delta: 7.72 (d, J=8.50 Hz, 1H), 6.58 (d, J=8.50 Hz, 1H), 3.92 (s, 3H); 13C-NMR (CDCl3, 125 MHz) delta: 162.4, 147.3, 143.8, 110.9, 110.1, 54.3; HR-MS (ESI-TOF): Calcd for C6H6BrClNO [(M+H)+] 221.9316. Found 221.9314.

Statistics shows that 17228-64-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-6-methoxypyridine.

Reference:
Article; Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 723 – 732;,
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. 119285-07-3, name is tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

4-(5-Amino-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (1.5 g), 3-Chloro- benzo[l,2,4]triazine 1 -oxide (1.2 g) and DMF (20 ml) and potassium carbonate (1.5 g) were heated to 50-60 C and stirred over night. On completion, water (200 ml) was added and extracted with ethyl acetate (2×200 ml). The combined organic extracts were dried over sodium sulfate. The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 25% EtOAc/n-hexane) to yield 4-[5-(l-Oxy- benzo[l,2,4]triazin-3-ylamino)-pyridin-2-yl]-piperazine-l-carboxylic acid tert-butyl ester.

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Reference:
Patent; SENTINEL ONCOLOGY LIMITED; WO2006/131835; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1018949-67-1, 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 1018949-67-1 as follows.

General procedure: In a three neck round bottom flask (50 mL in volume) along with guard tube was charged with carboxylic acid (1.0 equiv) in 5 ml solvent combination of CH2Cl2: DMF (4:1). After few minutes stirring at room temperature the resulting suspension was cooled with an ice-water bath prior to the addition of the bis(2-oxo-3-oxazolidinyl)phosphonic chloride (1.5 equiv) and the starting compound 1a (1.0 equiv). The resulting mixture was stirred again for few minutes and then DIPEA (3.0 equiv) was added. The mixture was kept at 0 C for 30-60 min and then stirred at room temperature until the starting material was consumed as monitored by TLC analysis. Ice-water (20 mL) was added while maintaining vigorous stirring. In the cases when the indole precipitated upon addition of water, the solid was filtered off and dissolved in EtOAc (20 mL). In all other cases, the aqueous layer was extracted with EtOAc (3 × 20 mL). The extracts were combined and washed with water (2 × 50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified either by silica gel chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018949-67-1, its application will become more common.

Reference:
Article; Jadhav, Jagannath; Khanapaure, Sharanabasappa; Kurane, Rajanikant; Salunkhe, Rajashri; Rashinkar, Gajanan; Tetrahedron Letters; vol. 54; 50; (2013); p. 6858 – 6863;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74420-15-8, Adding some certain compound to certain chemical reactions, such as: 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H5BrN2, 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 74420-15-8.

Example 79 Synthesis of (2-Ethoxy-naphthalen-1-yl)-[3-(4-methanesulfonyl-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-methanone 84 Step 1-Preparation of (3-Bromo-pyrrolo[2,3-b]pyridin-1-yl)-(2-ethoxy-naphthalen-1-yl)-methanone 85 3-Bromo-7-azaindole (500 mg, 2.0 mmol) 3 was dissolved in N,N-dimethylformamide (50 mL) and sodium hydride (210 mg, 5.3 mmol, 60% dispersion in mineral oil) and 2-Ethoxy-naphthalene-1-carbonyl chloride (710 mg, 3.0 mmol) were added. The reaction mixture was stirred at ambient temperature for 30 min, cast into ice water (100 mL) and extracted into ethyl acetate. The organic portion was dried with anhydrous magnesium sulfate, filtered and the filtrate concentrated. Purification via column chromatography (10% Ethyl acetate in hexanes) provided the desired product 85 (800 mg, 80%).

According to the analysis of related databases, 74420-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ibrahim, Prabha N.; Bremer, Ryan; Gillette, Sam; Cho, Hanna; Nespi, Marika; Mamo, Shumeye; Zhang, Chao; Artis, Dean R.; Lee, Byunghun; Zuckerman, Rebecca; US2006/100218; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1678-53-1 ,Some common heterocyclic compound, 1678-53-1, molecular formula is C6H6N2O2, 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: To a stirred mixture of 1.00 mmol of nitropicoline 35 or 63, 1.20 mmol of the appropriate benzaldehyde, and 1.5 mmol of Huenig’s base in THF (7 mL/g of nitropicoline 35/63) was added 1.3 mmol of a 1 M THF solution of TBAF. The resulting mixture was heated 60 C for 1.5e2.0 h in the case of 2,3-dihydrofuro[3,2-c] pyridines or for 18 h in the case of 2,3-dihydrofuro[2,3-b]pyridines. After cooling to room temperature, the reactions were quenched with sat. aqueous NH4Cl. The solution was extracted with EtOAc, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography as specified above.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1678-53-1, its application will become more common.

Reference:
Article; Kuethe, Jeffrey T.; Tetrahedron; vol. 75; 34; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem