Category: pyridine-derivatives

Electric Literature of 52568-28-2 ,Some common heterocyclic compound, 52568-28-2, molecular formula is C8H12N2, 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 solution of the acid (1 equiv.) in DCM (0.2 M) were added EDCI (1.2 equiv.), HOBt (1.2 equiv.), DIPEA (1.2 equiv.) at 0 C. After the mixture was stirred for 10 min, the amine (1.2 equiv.) was added. The reaction was stirred overnight at room temperature. Then water was added and the mixture was extracted with DCM. The combined organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography on silica gel to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52568-28-2, its application will become more common.

Reference:
Article; Wang, Haifeng; Niu, Youhong; Zhang, Guoying; Ye, Xin-Shan; Tetrahedron Letters; vol. 57; 41; (2016); p. 4544 – 4548;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16110-09-1, 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 16110-09-1 as follows.

Step 1 Synthesis of Ethyl 5-chloropyridin-2-carboxylate: 1.2 g (8.2 mmol) of 2,5-dichloropyridine was dissolved in 50 ml of acetonitrile. 1.46 g (9.7 mmol) of sodium iodide and 0.7 ml (9.7 mmol) of acetyl chloride were added to the obtained solution, and they were stirred at 50 C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 15 ml of DMF. 182 mg (0.8 mmol) of palladium acetate, 147 mg (0.56 mmol) of triphenylphosphine, 2.3 ml of ethanol and 1.3 ml (9.7 mmol) of triethylamine were added to the obtained solution, and they were stirred in the presence of carbon monoxide at 70 C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound. Yield: 250 mg (1.35 mmol) (16%) H-NMR (CD3Cl) delta 1.44 (3H, t), 4.47 (2H, d), 7.82 (1H, dd), 8.09 (1H, d), 8.69 (1H, d)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16110-09-1, its application will become more common.

Reference:
Patent; AJINOMOTO CO. INC; US2003/186969; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6937-03-7, 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 6937-03-7 as follows.

To solution of (2,4,5-trichloro-phenoxy)-acetic acid (150 mg, 0.59 mmol), 2-amino isonicotinic acid methyl ester (179 mg, 1.18 mmol) and DMAP (144 mg, 1.18 mmol) in DMF 13 mL was added PyBOP (614 mg, 1.18 mmol) at room temperature. Reaction mixture was stared at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:1) to give 2-[2-(2,4,5-trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.056 g, 24.45% yield). 1H NMR (DMSO-d6, 300 MHz) 10.89 (1H, s, CONH), 8.54 (2H, d, J=5.4 Hz, pyridine), 7.85 (s, 1H, aromatic), 7.58 (1H, dd, J=1.35 &4.95 Hz, pyridine), 7.48 (1H, s, aromatic), 5.05 (2H, s, OCH2), 3.89 (3H, s, OCH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6937-03-7, its application will become more common.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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.

Example 140 To a suspension of NaH (60% dispersion in mineral oil, 1.34 g, 0.056 mol) in THF (10 mL), a solution of 5-bromopyridin-2-ol (2.5 g, 0.014 mol) in THF (50 mL) was added and the resulting mixture was stirred at RT for 1 h. To this mixture, iodoethane (10.9 g, 0.07 mol) was added and the mixture was stirred at RT overnight. The mixture was quenched with water and washed with NH4Cl solution. The organic phase was separated, then concentrated in vacuo and the residue was purified by flash chromatography on silica gel (50-100% PE-AE) to afford 5-bromo-1-ethylpyridin-2(1H)-one.

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 13466-38-1, 5-Bromopyridin-2-ol.

Reference:
Patent; INTELLKINE, LLC; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo C.; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel A.; TREMBLAY, Martin R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; US2013/53362; (2013); 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.94413-70-4, name is 4-(Aminomethyl)-2-methylpyridine, molecular formula is C7H10N2, molecular weight is 122.1677, as common compound, the synthetic route is as follows.Safety of 4-(Aminomethyl)-2-methylpyridine

To a stirred solution of 3-(3,4-dimethoxyphenyl)-8-iodo-2,6-dimethylimidazo[l,2-b]pyridazine (0.1 g, 0.240 mmol) and (2-methylpyridin-4-yl)methanamine (0.06 g, 0.312 mmol) in toluene (2 mL) was added cesium carbonate (0.156 g, 0.48 mmol), 2,2′-bis(diphenylphosphino)-l ,l ‘- binaphthyl (BINAP (7 mg, 0.012 mmol) and Pd(OAc)2 (2 mg, 0.012 mmol). The reaction was stirred at l05C for l6h. Upon completion, the reaction was diluted with 10% MeOH-CH2Cl2 and filtered through a celite bed. The filtrate was concentrated and the obtained solid was washed with acetonitrile to afford 3-(3,4-dimethoxyphenyl)-2,6-dimethyl-N-((2-methylpyridin-4- yl)methyl)imidazo[l,2-b]pyridazin-8-amine (0.09 g, 91.83%) as a pale brown solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,94413-70-4, 4-(Aminomethyl)-2-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; CUROVIR AB; WESTMAN, Jacob; (78 pag.)WO2020/74160; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 156118-16-0, 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. 156118-16-0, name is 3-Amino-6-bromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

To a solutionof 27(4.00 g, 21.4 mmol) in AcOH (300 ml) was added NaNO2 (1.48 g, 21.4mmol) and stirred overnight at roomtemperature. The reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc and washed with saturatedNaHCO3 aqueous solution and brine. Theorganic layer was dried over anhydrous MgSO4 and reduced underpressure. The residue was purified bysilica gel column chromatography (0-50% EtOAc in hexanes) to afford 28 as a yellow solid (2.48 g, 59%yield).1H NMR (300 MHz, CDCl3): delta ppm7.86 – 7.90 (m, 1 H), 8.09 – 8.14 (m, 1 H), 8.83 – 8.88 (m, 1 H).MS ESI/APCI Dual m/z: 198 [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,156118-16-0, its application will become more common.

Reference:
Article; Matsuda, Daisuke; Kobashi, Yohei; Mikami, Ayako; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Hamada, Makoto; Oda, Koji; Nishimoto, Shinichi; Kimura, Kayo; Miyoshi, Masako; Takayama, Noriko; Kakinuma, Hiroyuki; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3441 – 3446;,
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. 69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, 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. Safety of Thieno[3,2-b]pyridin-7(4H)-one

A stirred suspension of thieno[3,2-b]pyridin-7-ol (1, 5.0 g, 33.1 mmol) in POCls(15 mL) was heated to 105C in an oil bath for 4 hrs. The resultant solution was cooled toroom temperature and the POCls was removed under reduced pressure. The residue wascooled in an ice/water bath and cold water was added. The water was made basic withconcentrated NlrLtOH solution and extracted with EtOAc. The organic extract was driedover anhydrous sodium sulfate and concentrated to produce an oil which was purified bycolumn chromatography (eluent EtOAc-hexane, 1:4) to afford the title compound as abrown solid (4.5 g, 72% yield). .H NMR (400 MHz, CDC13) 8 (ppm): 8.60 (d, J= 4.9 Hz,1H), 7.80 (d, J= 5.5 Hz, 1H), 7.60 (d, J= 5.5 Hz, 1H), 7.30 (d, J= 4.9 Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 69627-02-7.

Reference:
Patent; METHYLGENE, INC.; WO2006/10264; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 108-96-3, Pyridin-4(1H)-one, 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, Product Details of 108-96-3, blongs to pyridine-derivatives compound. Product Details of 108-96-3

Example 45; 4-[[2-(4-Pyridinyloxy)ethyl](2,2,2-trifluoroethyl)amino]-2- (trifluoromethyl)benzonitrile; Synthesized as described in Example 1C from 4-[(2-hydroxyethyl)(2,2,2- trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile and 4-pyridone, using dry DME as reaction solvent: 1H NMR (400 MHz, CDCI3) delta 8.45 (dd, J = 5.0, 1.3 Hz, 2H), 7.68 (d, J = 8.8 Hz, 1 H), 7.18 (d, J = 2.5 Hz, 1 H), 7.01 (dd, J = 8.7, 2.6 Hz, 1 H), 6.77 (dd, J = 4.9, 1.3 Hz, 2H), 4.27 (t, J = 5.2 Hz, 2H), 4.19 (q, J = 8.5 Hz, 2H), 4.04 (t, J = 5.3 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108-96-3, Pyridin-4(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/44707; (2006); 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.152460-09-8, name is N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine, molecular formula is C16H13N5O2, molecular weight is 307.31, as common compound, the synthetic route is as follows.Application In Synthesis of N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

In to a hydrogenation kettle a N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2- pyridineamine (20 g; 0.0.0651 mol) obtained from step-B and methanol (400ml) were added. Wet Raney’s nickel (8g) was washed thoroughly with water and was charged into hydrogenation kettle. Hydrogenation was conducted at 60psi at 25C for 45hours. The reaction mixture was filtered and washed with methanol (200ml). The combined filtrates were concentrated in vacuum, treated with a mixture of water (100ml) and chloroform (200 ml). The organic layer was washed with water (3x50ml) and distilled under vacuum. Residual solid was brought to room temperature and ethyl acetate (150ml) was charged. The solution was heated to reflux temperature and cooled down with stirring to 0-5C. The crystalline solid was filtered off and washed with chilled ethyl acetate (10ml), dried to afford title compound (15.0g, yield: 82.7%) of the title product. Purity (by HPLC): 99.40%) Melting point: 143-147C

At the same time, in my other blogs, there are other synthetic methods of this type of compound,152460-09-8, N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala Kishan; RACHAKONDA, Sreenivas; GAMPA, Venu Gopala Krishna; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2013/35102; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54923-31-8, 5-Bromo-6-methylpyridin-2-ol, 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, 54923-31-8, blongs to pyridine-derivatives compound. Safety of 5-Bromo-6-methylpyridin-2-ol

Step B.4-(5-Bromo-6-methyl-pyridin-2-yloxy)-butyric acid, ethyl ester A mixture of 5-bromo-6-methyl-pyridin-2-ol (1.3 g, 6.9 mmol), 4-bromo-butyric acid ethyl ester (2.7 g, 13.8 mmol) and K2C03 (2.8 g, 20.7 mmol) in DMF (20 mL) was heated at 110C under a dry N2 atmosphere for 16 h. After cooling, the mixture was diluted with 200 mL of H2O, and twice extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (EA/PE=1/10) to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54923-31-8, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); A1;; ; Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William, K.; LI, Bing; SZEWCZYK, Jason, W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi, P.; PIO, Barbara; DANG, Qun; LIN, Linus, S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/95256; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem