Pyridine-derivatives

Related Products of 1026796-81-5, 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.1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

Intermediate 80: N-(4-(2-(Hydroxymethyl)-5-methyl-4-oxo-4,5-dihydrofuro[3,2-c]pyridin-7-yl)pyridin-2-yl)acetamide. 4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolane (1 1.13 mL, 77 mmol) was added to a mixture of 7-bromo-2- (hydroxymethyl)-5-methylfuro[3,2-c]pyridin-4(5/-/)-one (for a preparation see Intermediate 78, 3.3 g, 12.79 mmol) and triethylamine (10.71 mL, 77 mmol) in 1 ,4-dioxane (20 mL) and the mixture was stirred for 5 min under nitrogen. Pd(PPh3)4 (1.478 g, 1 .279 mmol) was added and the mixture heated to 100C for 18 h. The mixture was cooled in an ice bath, then isopropanol (20.00 mL) was added, initially very cautiously, followed by water (10 mL), potassium carbonate (5.30 g, 38.4 mmol), PEPPSI-SIPr (0.871 g, 1.279 mmol) and A/-(4-bromopyridin-2-yl)acetamide (for a preparation see Intermediate 79, 3.02 g, 14.07 mmol). The mixture was heated to 80C for 2 h under nitrogen, then allowed to stand over the weekend. The mixture was diluted with ether (100 mL) and stirred for 10 min, then filtered and the solid was washed with water (50 mL) and dried under vacuum for 10 min to give the crude product. The resulting solid was heated in methanol (50 mL) to reflux, then cooled in an ice bath and the solid product collected by filtration to give A/-(4-(2-(hydroxymethyl)-5-methyl-4- oxo-4,5-dihydrofuro[3,2-c]pyridin-7-yl)pyridin-2-yl)acetamide (2.76 g, 8.81 mmol, 68.9 % yield) as a colourless solid. 1H NMR (400MHz, DMSO-of6) delta-ppm 10.53 (1 H, s), 8.50 (1 H, s), 8.38 (1 H, d), 8.13 (1 H, s), 7.48 (1 H, m), 6.85 (1 H, s), 5.46 (1 H, m), 4.55 (2H, d), 3.61 (3H, s), 2.13 (3H, s). LCMS (2 min, Formic): Rt = 0.55 min, MH+ 314.

Statistics shows that 1026796-81-5 is playing an increasingly important role. we look forward to future research findings about N-(4-Bromopyridin-2-yl)acetamide.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine. A new synthetic method of this compound is introduced below., Quality Control of 6-Chloro-4-methylpyridin-3-amine

Compound 6-chloro-4-methylpyridin-3-amine la (568 mg, 4.0 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.22 g, 4.0 mmol), cesium carbonate (3.8 g, 12 mmol), [1,1′-bis(diphenylphosphine)ferrocene]palladium dichloride dichloromethane adduct (146 mg, 0.2 mmol), 1,4-dioxane (30 mL), and water (7 mL) were mixed, degassed, and heated to reflux under nitrogen for 16 hrs. The mixture was cooled to room temperature and concentrated to remove solvent under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 20/1 to 2/1) to produce the target compound tert-butyl 5-amino-4-methyl-5′,6′-dihydro-[2,3′-dipyridyl]-1′(2’H)-carboxylate 1b (401 mg, yellow oil), yield: 34%. MS m/z (ESI):290[M+1]

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, 66909-38-4, 6-Chloro-4-methylpyridin-3-amine.

Reference:
Patent; Beijing InnoCare Pharma Tech Co., Ltd.; CHEN, Xiangyang; PANG, Yucheng; (44 pag.)EP3409672; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 130473-27-7, 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. 130473-27-7, name is 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Coupling: Example 24 is obtained as a white solid (40% yield) using acid C176 using Method C with non-critical changes. HRMS (FAB) calculated for C15H18N4O+H: 271.1559, found 271.1562 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130473-27-7, 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1235036-15-3, Adding some certain compound to certain chemical reactions, such as: 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate,molecular formula is C10H11BrClNO2, 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 1235036-15-3.

To Example 1.1.10 (100 mg) and tert-butyl3-bromo-6-chloropicolinate (52.5 mg) in dioxane(2 mL) was added tris(dibenzylideneacetone)dipalladium(O) (8.2 mg), K3P04 (114 mg), 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (5.24 mg) and water (0.8 mL). The mixturewas stirred at 95 oc for 4 hours, diluted with ethyl acetate and washed with water and brine. Theorganic layer was dried over Na2S04 , filtered, concentrated and purified by flash chromatography,eluting with 20% ethyl acetate in heptanes and then with 5% methanol in dichloromethane, to providethe title compound. MS (ESI) m/e 643.3 (M+Ht

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. 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; JUDD, Andrew, S.; PHILLIPS, Andrew, C.; SOUERS, Andrew, J.; BRUNCKO, Milan; (503 pag.)WO2017/214301; (2017); 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.39903-01-0, name is 2-Amino-5-bromo-3-pyridinol, molecular formula is C5H5BrN2O, molecular weight is 189.01, as common compound, the synthetic route is as follows.COA of Formula: C5H5BrN2O

Preparation 56-Bromo-oxazolo[4,5-b]pyridine[00122] 2-Amino-5-bromo-3-hydroxypyridine (200 mg, 1.06 mmol) is dissolved in 3 ml of triethylortoformate and a catalytic amount of p-toluenesulfonic acid is added. The mixture is heated to reflux for 5 h, then cooled, diluted with DCM and washed with saturated sodium bicarbonate solution. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by flash column chromatography to afford 212 mg (60%) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39903-01-0, 2-Amino-5-bromo-3-pyridinol, and friends who are interested can also refer to it.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints; WO2011/15343; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 709652-82-4, 2-Amino-5-bromonicotinonitrile, 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, name: 2-Amino-5-bromonicotinonitrile, blongs to pyridine-derivatives compound. name: 2-Amino-5-bromonicotinonitrile

A suspension of 2-amino-5-bromo-3-pyridinecarbonitrile (0.59 g, 3 mmol), DMF-DMA (1 ml, 7.5 mmol), and MeCN (2 ml) was irradiated at 50 C (input power of: 200 W) for2 min. The resulting mixture was cooled to room temperature and poured onto ice cold water. The precipitate was filtered off, washed with water, and dried to afford (1E)-N?-(3-cyano-2-pyridinyl)-N,N-dimethylmethanimidamide (Lacbay et al. 2014). Light yellow solid; yield 95%; m.p. 116-117 C; 1H NMR (400 MHz, DMSO-d6) delta 8.65-8.60 (m, 1H, H-5), 8.46 (d, J = 2.6 Hz, 1H, H-3), 8.32 (d,J = 2.6 Hz, 1H, N=CH), 3.16 (s, 3H, CH3),3.07 (s, 3H,CH3); 13C NMR (100 MHz, DMSO-d6) delta 162.27 (C-2),157.00 (C=N), 153.23 (C-6), 144.32 (C-4), 116.77 (CN), 110.23 (C-5), 102.68 (C-3), 35.00 (C-N); IR (film): 3457(C-N), 3061, 2916, 2795, 2483, 2306, 2214 (CN), 1960, 1625 (C=N), 1562, 1395 cm-1; HRMS (ESI) m/z: calculatedfor C9H10BrN4+ [M + H]+: 253.0089; found: 253.0084.

The synthetic route of 709652-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Ya-Quan; Zong, Chao-Yang; Ji, Jin-Yu; Han, Qing; Chemical Papers; vol. 72; 12; (2018); p. 2965 – 2972;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 175204-80-5 , The common heterocyclic compound, 175204-80-5, name is 3-Amino-4-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, 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.

Preparation III; 4-(Trifluoromethyl)-3-pyridinol; A solution of 2 g (12.34 mmol) of 3-amino-4-(trifluoromethyl)pyridine in 28 ml of 50% sulfuric acid is cooled to -5 C. and a solution of 1.03 g (14.8 mmol) of sodium nitrite in 10 ml of water is added slowly. The mixture is left to return to room temperature and stirring is continued for 30 min. 25 ml of concentrated sulfuric acid are then added and the reaction mixture is stirred at 100-110 C. for 2 hours. After cooling, the reaction medium is neutralized by adding saturated sodium bicarbonate solution to pH 6-7, and the mixture is extracted with ethyl acetate. The organic phase obtained is washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 1.92 g of the expected compound in the form of a brown powder (yield=95%). M.p.=112-114 C.

The synthetic route of 175204-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratoires Fournier S.A.; US2007/54955; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, 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, Safety of tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, blongs to pyridine-derivatives compound. Safety of tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

[00316] fer -Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0. 3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2S03 (1.5 eq) was added via addition funnel. After completion of Na2S03 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2C03 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3- methylpyridine-1 -oxide (95%) that was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SWINNEY, Kelly, Ann; HURTER, Patricia, Nell; NADIG, David, E.; SMITH, David; THOMAS, Vance, Hayden; WARMAN, Martin, Paul; WO2015/73231; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 106047-28-3, 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 106047-28-3 as follows.

Step 2 1-methyl-4-nitro-2-[2-(3-pyridyl)pyridin-6-ylamino]benzene This compound was prepared by version of the method described in the document (J. Org. Chem., 2000, 65, 1144-1157.). To 940 mg of 2-bromo-6-(3-pyridyl)pyridine obtained in the step 1, 730 mg of 2-methyl-5-nitroaniline, 37 mg of tris(dibenzylideneacetone)dipalladium (0), 75 mg of (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [(+-)-BINAP] and 1.82 mg of cesium carbonate, 12 ml of toluene was added and the mixture was stirred with heating at 110C for 24 hours under an argon atmosphere. After air cooling, the reaction solution was diluted with ethyl acetate and insolubles were removed by filtration. The solvent in the filtrate was distilled off under reduced pressure and the residue was crystallized by adding diethyl ether. The resulting crystal was collected by filtration and then washed with ethyl acetate-diethyl ether to obtain 646 mg of the objective compound as a yellow crystal. Melting point: 148-150C 1H-NMR(CDCl3)delta: 2.42(3H, s), 6.53(1H, br), 6.80(1H, d), 7.35(2H, d), 7.44(1H, dd), 7.69(1H, m), 7.83(1H, dd), 8.44(1H, dt), 8.65(1H, dd), 9.09(1H, d), 9.20(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,106047-28-3, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1533304; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 898746-42-4 , The common heterocyclic compound, 898746-42-4, name is 6-Fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5FN2, 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.

6-Fluoro-1H-pyrrolo[2,3-b]pyridine (2.50 g, 18.36 mmol)Soluble in DMF (50mL),Cool to 0 C,Then add bromine to it(3.20g, 20.00mmol)DMF (20 mL) solution,After the dropwise addition was completed, the resulting reaction solution was stirred at room temperature for 2 hours.Then water (100 mL) was added and a large amount of solid precipitated.Filter under reduced pressure, and the filter cake was washed with water (30 mL×2).Then dried under vacuum at 60 C for 24 hours.The title compound was obtained as a white solid (3.44 g, 87%).

The synthetic route of 898746-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; Nie Biao; Xu Juan; Yan Huan; Chen Jianping; (90 pag.)CN108727369; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem