Category: pyridine-derivatives

Electric Literature of 677728-92-6 ,Some common heterocyclic compound, 677728-92-6, molecular formula is C6H4FNO, 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.

Example 6 Synthesis of 2-fluoro-5-[(E)-2-(4-methoxyphenyl)vinyl]pyridine (1f); Compound 1f was synthesized by Horner-Wadsworth-Emmons.10Synthe -fluoro-5-[(E)-2-(4-methoxyphenyl)vinyl1pyridine (1f)To a solution of diethyl [4-(meththoxy)benzyl]phosphonate (500 mg, 1 .94 mmol) and 6-fluoropyridine-3-carbaldehyde (242 mg, 1 .94 mmol) in DMF (4 mL) was added a solution of potassium tert.butylat (543 mg, 4.8 mmol) in DMF (16 mL). After stirring for one hour the reaction mixture was quenched with saturated aqueous ammonium chloride solution, extracted with dichloromethane, washed with brine and dried over sodium sulfate. The residue was purified by chromatography on silica gel (ethyl acetate in hexane 0 to 50%) to yield 50.6 mg (10.3%) of the title compound.1 H-NMR (400 MHz, CHLOROFORM-d) d = 3.85 (s, 3H), 6.92 (d, 1 H), 6.92 (dd, 1 H), 6.93 (d, 2H), 7.05 (d, 1 H), 7.46 (d, 2H), 7.93 (ddd, 1 H), 8.28 (d, 1 H) ppm. 19F-NMR (376 MHz, CHLOROFORM-d) delta = -70.13 (d, 1 F) ppm. MS ES+ m/z = 230.13 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BERNDT, Mathias; BROCKSCHNIEDER, Damian; HEINRICH, Tobias; BERGER, Markus; WO2011/141515; (2011); A1;,
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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;,
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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;,
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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;,
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Electric Literature of 7356-60-7, 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 7356-60-7, name is Nicotinimidamide hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

Compound B (124 g, 223.23 mmol),3-pyridinecarboxamidine hydrochloride (52.77g, 334.83mmol)With potassium phosphate (165.84g, 781.31mmol),1240 ml of xylene was placed in a reaction flask and heated with stirring to maintain reflux at 140 C.After the reaction was completed, the temperature was lowered to 90 C.Add 500ml of deionized water and stir for 5min.After removing the aqueous layer, the organic layer was concentrated to dryness and a solid precipitated out.The solid was washed with ethyl acetate and filtered to obtain a white solid.64g of white solid compound C was obtained after drying,Yield: 43.66%.

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 7356-60-7, Nicotinimidamide hydrochloride.

Reference:
Patent; E-RAY OPTOELECTRONICS TECHNOLOGY CO., LTD.; CHANGZHOU TRONLY E-RAY OPTOELECTRONICS MATERIAL CO., LTD.; HUANG, HEH LUNG; CHAO, TENG CHIH; GUO, HUANG MING; LIN, CHI JEN; CHANG, MIN JONG; (48 pag.)TWI672298; (2019); B;,
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Related Products of 1207557-35-4 ,Some common heterocyclic compound, 1207557-35-4, molecular formula is C11H11BrN2O3, 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.

Step B: DecarboxylationA solution of ethyl 6-bromo-4-methoxylpyrazolo[l,5-a]pyridine-3-carboxylate (15, 5.2 g, 18.24 mmol) in HBr (100 ml, 884 mmol) was heated to 100 0C for 1 hour. After cooling to 0 0C, IM NaOH (182 ml, 912 mmol) was used to neutralize the solution. The reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydroxide (IN) and brine then dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography (0-35% EtOAc in hexanes, linear gradient) to give 6-bromo-4- methoxypyrazolo[l,5-alpha]rhoyridine (16, 2.475 g, 10.90 mmol, 60 % yield). MS APCI: (M + H]+ m/z 228.1.; Scheme 2.Molecules of type 21 were prepared according to scheme 2. O- Mesitylenesulfonylhydroxylamine (1) was used to access W-imino-pyridinium mesitylenesulphonate 14. [3+2] Cyclization of 2 with ethyl propiolate yields pyrazolopyridine 15. Decarboxylation in neat hydrobromic acid afforded 16. Functional ization of the 6-position of the pyrazolopyridine core is accomplished via a Suzuki coupling reaction to install aryl or heteToaromatic functionality (17) using known or commercially available boronic acids or esters. For specific boronic ester examples, see WO 2004052286 A2 and WO 2007085873 Al . Halogenation via reaction with //-iodosuccinimide enables a second Suzuki coupling of iodide 18 with thiophcnc boronic ester to yield coupling product 19. Hydrolysis of the ester yielded acid 20 and subsequent coupling with an amine yielded target 21.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1207557-35-4, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; KATZ, Jason; KNOWLES, Sandra, L.; JEWELL, James, P.; SLOMAN, David, L.; STANTON, Matthew, G.; NOUCTI, Njamkou; WO2010/17046; (2010); A1;,
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Electric Literature of 139585-70-9 ,Some common heterocyclic compound, 139585-70-9, molecular formula is C6H3BrN2, 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.

10 mmol, 1.58 g), Na2CO3 (0.5 mmol, 57 mg), 2-bromo-5-cyanopyridine(0.1 mmol, 115 mg) was dissolved in a mixed solvent of toluene / ethanol / water (V: V = 5: 2: 1). After 24 hours of refluxing, the reaction was stopped and the reaction mixture was left to stand at room temperature , Washed with dichloromethane, and then the organic phase was collected and purified by silica gel column chromatography to obtain 2.1 g of 2- (2 ‘, 4’-difluorophenyl) -5-amidopyridine as a white solid (yield : 89%);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,139585-70-9, its application will become more common.

Reference:
Patent; UNIVERSITY OF SCIENCE AND TECHNOLOGY OF SUZHOU; ZHOU, YUYANG; WANG, XIAOMEI; YE, CHANGQING; ZHU, SAIJIANG; LIANG, ZUOQIN; (6 pag.)CN104016914; (2016); B;,
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Synthetic Route of 1195-59-1, Adding some certain compound to certain chemical reactions, such as: 1195-59-1, name is 2,6-Pyridinedimethanol,molecular formula is C7H9NO2, 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 1195-59-1.

A solution of (b) (1.39 g, 10 mmol) in 35 mL of CH2Cl2 was added to a 40% aqueous solution of KOH (35 mL). The reaction mixture was cooled at 0 C and stirred for 30 min, after which a solution of p-toluenesulfonyl chloride (3.81 g, 20 mmol) was added in one portion. The reaction mixture was stirred for 1 h at 0 C and then at room temperature until complete conversion (TLC, 1/4 methanol/toluene). The reaction mixture was added to water (35 mL). The aqueous phase was extracted with CH2Cl2 (3 * 20 mL), the combined organic phase was dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to afford a white crystalline solid (3.89 g, 87%) with Mp 119-121 C (121-122 C in [28] ). FT-IR (solid, cm-1): 3070, 3038 nu (C-H), 1596 nu (Cfx1C), 743 delta (C-H). 1H NMR (CDCl3), deltaH ppm: 2.46 (s, 6H, CH3), 5.08 (s, 4H, CH2), 7.34-7.83 (m, 11H).

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. 1195-59-1, 2,6-Pyridinedimethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Aghatabay, Naz Mohammed; Altun, Ahmet; Guerbuez, Mustafa Ulvi; Tuerkyilmaz, Murat; Comptes Rendus Chimie; vol. 17; 9; (2014); p. 905 – 912;,
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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. 24242-20-4, name is 5-Aminopicolinic acid, the common compound, a new synthetic route is introduced below. Quality Control of 5-Aminopicolinic acid

To a solution of 5-aminopicolinic acid (194 mg, 1.40 mmol) in ethanol (5 mL), was added thionyl chloride (0.20 mL, 2.80 mmol) at 0 C. The mixture was then stirred under reflux for 19 h, after which time it was cooled to room temperature and the reaction mixture concentrated under reduced pressure. Saturated aqueous sodium carbonate solution was added to the resulting solid to adjust the pH to 9, followed by saturated aqueous sodium hydrogen carbonate. Ethyl acetate (10 mL) and water (10 mL) were added and the organic phase was washed with brine (1 0 mL), dried (Na2SO4), filtered and the filtrate concentrated in vacuo. Ethyl 5-aminopicolinate (184 mg, 79%) was obtained as an off-white solid, with no need for further purification; 1H NMR (500 MHz, MeOD) 6 1 .37 (3H, t, J = 7.1 Hz, CH3), 4.35 (2H, q, J = 7.2 Hz), 7.02 (1H, dd, J = 2.7 and 8.6 Hz, Ar), 7.85 (1H, d, J = 8.6 Hz) and 7.98 (1H, d, J= 2.7 Hz). LRMS(ESI÷) mz 167.2 [M + H].

The synthetic route of 24242-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; REUILLON, Tristan; MILLER, Duncan; MYERS, Stephanie; MOLYNEUX, Lauren; CANO, Celine; HARDCASTLE, Ian; RIGOREAU, Laurent; GOLDING, Bernard; NOBLE, Martin; (246 pag.)WO2016/42341; (2016); A1;,
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Reference of 29682-15-3, 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 29682-15-3 as follows.

This compound is synthesized as described by adaptation of the following reference: Tye et al., Tet. Lett., 2008, 49, 3939. To a stirred suspension of methyl-5-bromo-2- pyridine carboxylate (0.25 g, 1.16 mmol) and 2-(trimethylsilyl)pyridine (0.48 mL), 3.48 mmol) in anhydrous N,N-dimethyl formamide (7.5 mL) is added silver (I) oxide (0.27 g, 1.16 mmol), allyl palladium chloride dimer (21 mg, 5 mol%) and tetrabutyl ammonium fluoride (IM in THF, 0.116 mL). The reaction is heated at 90 0C for 18 h. The reaction mixture is filtered and washed with EtOAc. The filtrate is concentrated under reduced pressure. Purification by column chromatography (silica, eluent DCM, 0- 2% MeOH) gives 0.12g (48%) of methyl 2,3′-bipyridine-6′-carboxylate. m/z = 215 [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,29682-15-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COGAN, Derek; MOSS, Neil; SARKO, Christopher Ronald; BAMFORD, Samantha Jayne; LOKE, Pui Leng; NAPIER, Spencer Charles, R.; TYE, Heather; WHITTAKER, Mark; WO2010/80357; (2010); A1;,
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