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. 74115-13-2, name is 5-Bromo-3-pyridinol. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

To a solution of 5-bromopyridin-3-ol (L) (174 mg, 1.0 mmol) in DMF (3 mL) was added potassium carbonate (415 mg, 3.0 mmol). The slurry was heated at 90C for 1 h and then cooled to 25C. The (bromomethyl)benzene (LIV) ( 171 mg, 1.0 mmol) was added and the mixture was stirred at 25C overnight. The reaction was worked-up using a saturated sodium bicarbonate and EtOAc extraction. The product was purified by ISCO column (40- 100% EtOAc-hexanes). The 3-(benzyloxy)-5-bromopyridine (LV) (105 mg, 0.398 mmol, 39.8 % yield) was obtained as yellow oil. ESIMS found for C12H10BrNO m/z 266.1 (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, 74115-13-2, 5-Bromo-3-pyridinol.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil, Kumar; WALLACE, David, Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (279 pag.)WO2017/23973; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-72-0 ,Some common heterocyclic compound, 1620-72-0, molecular formula is C7H6F3N, 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 2-methyl-6-(trifluoromethyl)pyridine (22.2 g, 138 mmol) in toluene (200 mL) was added mCPBA (23 g, 150 mmol). The reaction mixture was refluxed for 24 h under N2 atmosphere and quenched with saturated NH4CI solution. The resulting mixture was extracted with EtOAc (2 x 150 mL). The combined organic layers were washed with brine, dried over Na2S04, and concentrated in high vacuum. The residue was purified by silica gel chromatography (PE/EtOAc=5/l to 1/1) to give the title compound (5.5 g, yield : 22%); m/z (ES+) : 178 [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,1620-72-0, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; BLADH, Haakon; FELDING, Jakob; ZHOU, Ding; CAI, Zhen-wei; SØRENSEN, Morten Dahl; WO2015/24878; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1480-65-5, 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 1480-65-5 as follows.

[0271] A mixture of 5-chloro-2-fluoropyridine (2 g, 15.21 mmol), N, N-dimethylformamide (40 mL), phenylmethanethiol (2 g, 16.10 mmol), and CS2CO3 (7.52 g, 23.08 mmol) was stirred for 16 h at room temperature. The resulting solution was stirred for 6 h at 60°C. The solids were filtered out. The residue was dissolved in ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1 : 10) to afford the title compound (3 g, 83.7percent) as colorless oil. LCMS [M+H+] 236.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1480-65-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; VERMA, Vishal; VOLGRAF, Matthew; HU, Baihua; (105 pag.)WO2018/29288; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 573762-62-6, 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 573762-62-6 as follows.

0.8 g of 2-cyano-3-trifluoromethyl-5-aminopyridine was added to 20 ml of water.Stir vigorously,0.5 ml of thiophosgene was added dropwise over 30 minutes.After the addition, stirring was continued for 2 hours. The reaction mixture was extracted with chloroform (3×150 mL).The solid was filtered off, and the filtrate was evaporated to dryness under reduced pressure.I got ii-2 0.7 grams.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,573762-62-6, its application will become more common.

Reference:
Patent; Beijing Mei Bei Ta Pharmaceutical Co., Ltd.; Zhong Bohua; Fu Renfang; (10 pag.)CN109422725; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1603-40-3, 3-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, Product Details of 1603-40-3, blongs to pyridine-derivatives compound. Product Details of 1603-40-3

General procedure: 3-Chlorophenyl isothiocyanate and phenyl isothiocyanate (1.9 mmol and 3.7 mmol) was dissolved in 10 mL dichloromethane at 0 C. Then aniline (2.7 mmol and 5.5 mmol), was added dropwise with constant stirring, and completion of reaction is checked by TLC analysis. After 45 min a white solid appeared, the resultant solid product was filtered, washed with hexane, triturated with 10 mL of dichloromethane and excess of hexane and dried under vacuum. Recrystallization with methanol afforded the desired solid thiourea 1-38.

The synthetic route of 1603-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khan, Khalid Mohammed; Naz, Farzana; Taha, Muhammad; Khan, Ajmal; Perveen, Shahnaz; Choudhary; Voelter, Wolfgang; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 314 – 323;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6959-47-3, Adding some certain compound to certain chemical reactions, such as: 6959-47-3, name is 2-(Chloromethyl)pyridine hydrochloride,molecular formula is C6H7Cl2N, 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 6959-47-3.

General procedure: N-ethyl diamine (550 mg, 6.24 mmol) was dissolved inCH2Cl2 (10 mL). Chloromethyl pyryidine HCl salt (3.07 g, 18.71 mmol)was added followed by water (10 mL). Solution of NaOH in water (1.8 gin 6 mL) was added drop wise and the reaction mixture was stirred atRT for 3 days. Water (50 mL) was added and product was extracted withCH2Cl2 (3×20 mL), dried over MgSO4, solvent volume reduced to ca.10 mL under vacuum and transferred to short chromatographic columnand purified with EtOAc/MeOH gradient (0-30% MeOH). All productswere isolated as viscous orange oils

According to the analysis of related databases, 6959-47-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Schaefer-Ramadan, Stephanie; Barlog, Maciej; Roach, Jim; Al-Hashimi, Mohammed; Bazzi, Hassan S.; Machaca, Khaled; Bioorganic Chemistry; vol. 87; (2019); p. 366 – 372;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1462-86-8, 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. 1462-86-8, name is 3-Aminopicolinic acid. A new synthetic method of this compound is introduced below.

1. Reactions which are covered by Scheme 1; Example 1.1: Preparation of 2-amino-nicotinic acid methyl ester; To a solution of 3-amino-pyridine-2-carboxylic acid (1 g) in methanol (8 ml) and toluene (10 ml), under nitrogen atmosphere, was added a solution of (trimethylsilyl)- diazomethane (3.625 ml) (2M in diethylether). When the effervescence from the reaction had subsided a further portion of (trimethylsilyl)diazomethane (3.625 ml) (2M in diethylether) was added. The reaction mixture was stirred at ambient temperature for 20 hours. The reaction was quenched by addition of acetic acid (0.2 ml). The mixture was concentrated and the residue partitioned between dichloromethane and aqueous potassium carbonate (5% by weight). The phases were separated and the aqueous phase was extracted with further dichloromethane. The combined organic extracts were dried over magnesium sulfate and concentrated to give 2-amino-nicotinic acid methyl ester as a light yellow solid (968 mg). IH-NMR (400 MHz, CDCl3): 8.21-8.23 (m, IH), 8.12-8.14 (m, IH), 6.61-6.64 (m, IH), 3.89 (s, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1462-86-8, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2009/90401; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63725-51-9, 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 63725-51-9, name is 6-Chloro-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate Gen-19-a (5 g, 32.6 mmol, 1 eq) is dissolved in DMF (30 mL). I2 (16.4 g, 64.6 mol, 2 eq) and KOH (6.8 g, 121 mmol, 3.7 eq) are added. The reaction mixture is stirred at rt for 3 h. Then the reaction is quenched with a 10% solution of Na2S2O3. The aqueous layer is extracted four times with 50 mL Et2O, three times with DCM and three times with DCM/ MeOH 9:1. The combined organic layers are dried over Na2SO4, after washing with brine (50 mL), filtered and concentrated to afford Gen-20-a.

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 63725-51-9, 6-Chloro-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; SANIERE, Laurent Raymond Maurice; HUCK, Jacques; DYKES, Graeme James; SCHMITT, Benoit Antoine; BLANC, Javier; BUTLER, Anna Sara; BONNATERRE, Florence Marie-Emilie; BEAUMONT, Stephane Nicolas Alain; US2015/80391; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128071-98-7 ,Some common heterocyclic compound, 128071-98-7, molecular formula is C5H3BrFN, 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.

[00208] Step 1 : To a solution of 4-bromo-2-fluoropyridine (5.0 g, 28.4 mmol) in DMSO (56.8 mL, 28.4 mmol) was sequentially added tetrahydro-2H-pyran-4-amine (3.30 g, 32.7 mmol) and cesium carbonate (18.5 g, 56.8 mmol). The mixture was then stirred at 80 C for 4 hours and cooled to ambient temperature. The mixture was then poured into water and extracted into EtOAc (200 mL). The combined organics were washed with half saturated brine (50 mL), dried (MgS04), filtered and concentrated in vacuo. The crude isolated was purified by flash chromatography (Ready Sep 120 g) eluting with a gradient of 1-10% MeOH:DCM (10 CV) to provide 4-bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2 -amine (2.80 g, 38.3% yield). LCMS (APCI+) m/z 257, 259 (M+l) with one bromine isotope.

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. 128071-98-7, 4-Bromo-2-fluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; COOK, Adam; GAUDINO, John; GUNAWARDANA, Indrani, W.; HICKEN, Erik, James; HUNT, Kevin, W.; LYON, Michael; METCALF, Andrew, T.; MOHR, Peter, J.; MORENO, David, A.; NEWHOUSE, Brad; REN, Li; SCHWARZ, Jacob; CHEN, Huifen; GAZZARD, Lewis; SCHMIDT, Jane; DO, Steve; WO2015/103137; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1222185-12-7, 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 1222185-12-7 as follows.

(E)-Dimethyl 3-styrylpyridine-2,4-dicarboxylate Z4’A stirred suspension of 3-bromopyridine 11 (500 mg, 1.82 mmol, 1 eq.), (E)-styryl boronic acid (300 mg, 2.01 mmol, 1.1 eq.), Cs2CO3 (650 mg, 2.01 mmol, 1.1 eq.), Pd(OAc)2 (40 mg,0.182 mmol, 0.1 eq.) and PPh3 (100 mg, 0.365 mmol, 0.2 eq.) in anhydrous DMF (10 mL) was heated to 70 0C for 5 h in an oil bath. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo.The residue was purified by automated flash column chromatography (Biotage KP-SIL SNAP 25 g cartridge, eluting with EpsilontOAc/hexane) to afford Z4′ (322 mg, 60%) as an off-white solid.1U NMR deltaH (400 MHz; CDCl3) 3.86 (s, 3H, OCH3), 3.89 (s, 3Eta, OCH3), 6.59 (d, J=16.5 Hz, IH, CH=CH), 7.23-7.30 (t, J=8.0 Hz, IH, ArHpara), 7.34 (t, J=8.0 Hz, 2H, ArHmeta), 7.46 (d, J=7.0 Hz, 2H, ArHortho), 7.64 (d, J=16.5 Hz, IH, CH=CH), 7.71 (d, J=5.0 Hz, IH, pyHmeta), 8.65 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 52.8 (CH3), 52.8 (CH3), 123.5 (CH=CH), 124.6 (ArCH), 126.7 (ArCH), 128.4 (ArCH), 128.7 (ArCH), 133.0 (ArQ, 135.1 (CH=CH), 136.5 (ArQ, 139.0 (ArQ, 147.9 (ArCH), 149.8 (ArQ, 166.5 (CO), 166.7 (CO); IR vmax (filmycrn 1 2953, 1735, 1447, 1434, 1313, 1269, 1197, 1166, 1143, 1130; HRMS (EpsilonSI+) for C17H15NNaO4 requires 320.0893, found (M+Na*) 320.0893;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1222185-12-7, its application will become more common.

Reference:
Patent; ISIS INNOVATION LIMITED; SCHOFIELD, Christopher, Joseph; MCDONOUGH, Michael; ROSE, Nathan; THALHAMMER, Armin; WO2010/43866; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem