Category: pyridine-derivatives

Synthetic Route of 849937-96-8, 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.849937-96-8, name is 5-Bromo-2,4-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.8861, as common compound, the synthetic route is as follows.

To a stirred solution of 5-bromo-2,4-dichloropyridine (3.0 g, 13.22 mmol),isopropylamine (1.7 mL, 19.83 mmol), and Hunig?s Base (11.6 mL, 66.1 mmol) in DMF(5 mL) at room temperature was then heated at 120 C behind a safety shield for 4 hours,at which point it was judged to be complete by LCMS. The reaction mixture was diluted with ethyl acetate and washed 10% LiC1 (3x). The organic layer was dried over Na2SO4, filtered and concentrated to afford the crude product. The product was purified by column chromatography (hexanes/EtOAc) to afford 5 -bromo-2-chloro-N-isopropylpyridin-4-amine (1.29 g, 37% yield) as a colorless oil. LCMS m/z 249.0 (M+H).

Statistics shows that 849937-96-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2,4-dichloropyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUNCIA, John V.; GARDNER, Daniel S.; HYNES, John; MACOR, John E.; SANTELLA, Joseph B.; WU, Hong; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; SARKUNAM, Kandhasamy; SISTLA, Ramesh Kumar; POLIMERA, Subba Rao; (72 pag.)WO2016/210037; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 573675-25-9, 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. 573675-25-9, name is 5-Bromo-3-nitropicolinonitrile, molecular formula is C6H2BrN3O2, 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.

To asolution of tetrabutyl-ammonium fluoride (TBAF, 51.2 g, 197.4 mmol, 1.5eq) in DMF (100 mL), 4 A Molecular sieves powder (30 g) were added. The resulting mixture was stirred for 30 minutes. The mixture was filtered and the filtrate was transferred into a 1000 mL reaction flask. A solution of compound 88 (30 g,131.6 mmol, l .Oe q) in DMF (50 mL) was added to the above solution via a addition funnel over 10 minutes, while maintaining the internal temperature below -15C. After stirring for 20 minutes, 2 N HC1 (60 mL) was added over 5 minutes. After aging for1 hour, the mixture was cooled to 2.5C and filtered. The filtration cake was washed by DMF/water (10% (v/v), 2 x 36 mL). The filtrate was combined and concentrated in vacuo. The resulting residue was re-crystallized from 2-propanol (50 mL) to afford the desired compound 89 (13 g).

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 573675-25-9, 5-Bromo-3-nitropicolinonitrile.

Reference:
Patent; TIBOTEC PHARMACEUTICALS; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2012/13643; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2942-59-8, 2-Chloronicotinic acid, 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, Recommanded Product: 2942-59-8, blongs to pyridine-derivatives compound. Recommanded Product: 2942-59-8

EXAMPLE 18 3-Acetyl-2-chloropyridine The following is the preparation of a compound of Formula 2 in which t is 0, L is chloro, Y is N, Z is CH and R3 is acetyl. A mixture of 2-chloronicotinic acid (20 g, 0.127 mmol) and oxalyl chloride (13.3 mL, 0.152 mmol) in 2 drops of DMF and 200 mL of methylene chloride was stirred at room temperature for approximately 14 hours. The mixture was stirred at reflux temperature for 1 hour. The solution was cooled and partitioned between 100 mL of ice-cold aqueous sodium bicarbonate and 300 mL of methylene chloride. The organic layer was washed with brine, dried (Na2 SO4) and concentrated to give 2-chloronicotinic acid chloride (8.8 g, 49.5 mmol). A mixture of 2-chloronicotinic acid chloride (8.8 g, 49.5 mmol), tetramethyltin (5.5 mL, 40 mmol) and bis(benzonitrile)palladium(II) chloride (0.385 g) in 20 mL of hexamethylphosphoramide was stirred at room temperature for 20 hours. The mixture was stirred with 50 mL of 10percent potassium fluoride and then poured into 50 mL of water. The mixture was extracted with diethyl ether (4*50 mL) and the combined extracts were washed with water, saturated sodium bicarbonate and sodium chloride, dried (Na2 SO4) and concentrated. The residue was purified on silica gel by column chromatography eluding with hexanes/ethyl acetate (3:1) to give 3-acetyl-2-chloropyridine (4.2 g, 27 mmol).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2942-59-8, 2-Chloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5688795; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113975-22-7, 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. 113975-22-7, name is 2-Fluoro-3-iodopyridine, molecular formula is C5H3FIN, 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 5 – 2,2′-Difluoro-4,4′-diiodo-3,3′-bipyridine (5a) 2-Fluoro-3-iodopyridine (7.80 mmol, 1.74 g) was dissolved in 40 ml of anhydrous THF under nitrogen atmosphere and the solution was cooled in acetone/C02 bath. LDA (1.1 eq., 1.2 M in hexanes-THF, 8.58 mmol, 7.15 ml) was added dropwise. The reaction mixture became yellowish and after stirring for 0.5h it was analyzed by GC/MS. A clean BCHD reaction was confirmed, the mixture was stirred for additional 0.5h and CuCl2 (1.1 eq., 8.58 mmol, 1.15 g) was added in one portion. The yellow reaction mixture became dark blue, then brown red (within 1-2 h) and then light greenish after warm up to room temperature. The reaction mixture was treated with hexanes and water, the organic phase was removed, and the aqueous phase was extracted with hexanes (2 x -20 ml). The combined organic phases were dried over MgS04 and the solvent was removed by rotary evaporation to give greenish- brownish oil which partially solidified on standing. This crude product was purified by column chromatography (200 ml of silica gel, hexanes :CH2C12 mixtures (2: 1, 1 : 1 : and then 1 :2) as eluants). The solvents were removed from combined fractions and the product was obtained as off-white solid (1.04 g, 60.1%). UV-vis (CH2C12) max, nm226, 244, 268. HRMS (EI) calculated for Ci0H4F2I2N2 443.8432; found 443.8417. 1H NMR (CDC13, 400 MHz): delta 8.01 (d, J= 5.2 Hz, 2H), 7.82 (d, J= 5.2 Hz, 2H); 13C{1H} NMR (CDCI3, 100 MHz): delta 159.28 (d, J (C-F) = 242.8 Hz, quaternary C), 148.5 (d, J(C-F) = 15.62 Hz, CH), 132.1 (d, J(C-F) = 4.6 Hz, CH), 125.0 (dd, J (C-F) = 33.4 Hz, 4.1 Hz), 114.5 (d, J(C-F) = 1.7 Hz). Anal. Calc. for Ci0H4F2I2N2: C, 27.05; H, 0.91; N, 6.31. Found: C, 27.52; H, 0.84;

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 113975-22-7, 2-Fluoro-3-iodopyridine.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; GETMANENKO, Yulia A.; MARDER, Seth; HWANG, Do Kyung; KIPPELEN, Bernard; WO2013/23108; (2013); A1;; ; Patent; GEORGIA TECH RESEARCH CORPORATION; GETMANENKO, Yulia A.; MARDER, Seth; HWANG, Do Kyung; KIPPELEN, Bernard; WO2013/23106; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74115-12-1, 5-Chloro-3-hydroxypyridine, 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, 74115-12-1, blongs to pyridine-derivatives compound. COA of Formula: C5H4ClNO

General procedure: A 4-halonitrobenzene (1.0 equiv), a hydroxyarene, and Cs2CO3 (1.1 equiv) were combined in DMF and the resulting heterogeneous mixture was stirred vigorously at 25-70 C until all 4-halonitrobenzene was consumed (2-24 h). The reaction mixture was diluted with H2O and was adjusted to pH 5 with 2 N HCl (aq). The solution was extracted three times with EtOAc, and the organic layers were combined, washed once with brine solution, dried over MgSO4, filtered and concentrated in vacuo to furnish the desired diaryl ether that was used directly without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74115-12-1, its application will become more common.

Reference:
Article; Taygerly, Joshua P.; McGee, Lawrence R.; Rubenstein, Steven M.; Houze, Jonathan B.; Cushing, Timothy D.; Li, Yang; Motani, Alykhan; Chen, Jin-Long; Frankmoelle, Walter; Ye, Guosen; Learned, Marc R.; Jaen, Juan; Miao, Shichang; Timmermans, Pieter B.; Thoolen, Martin; Kearney, Patrick; Flygare, John; Beckmann, Holger; Weiszmann, Jennifer; Lindstrom, Michelle; Walker, Nigel; Liu, Jinsong; Biermann, Donna; Wang, Zhulun; Hagiwara, Atsushi; Iida, Tetsuya; Aramaki, Hisateru; Kitao, Yuki; Shinkai, Hisashi; Furukawa, Noboru; Nishiu, Jun; Nakamura, Motonao; Bioorganic and Medicinal Chemistry; vol. 21; 4; (2013); p. 979 – 992;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 875781-17-2, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Bromo-1H-pyrazolo[3,4-b]pyridine

Step 1: Synthesis of morpholin-4-yl-[3-(lH-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone.[0227] A mixture of 5-bromo-l^pyrazolo[3,4-b]pyridine (1.50 g, 7.57 mmol), 3-(morpholin-4-carbonyl)phenylboronic acid (2.136 g, 9.09 mmol) andtetrakis(triphenylphosphine)palladium(0) (435 mL, 0.376 mmol) in dimethoxyethane (8mL) and saturated aqueous solution of sodium bicarbonate (8 mL) was irradiated in aPersonal Chemistry Optimizer at 175 C for 60 min. The crude reaction mixture wasdistributed between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The aqueous phase was then extracted with dichloromethane, and then ethylacetate and the combined organic phases were dried over sodium sulfate, filtered andconcentrated to afford a pale green foam containing 80 % of morpholin-4-yl-[3-(lJfZ-pyrazolo[3,4-b]pyridm-5-yl)-phenyl]-methanone (2.30 g, 80 % yield) and 20 % oftriphenylphosphine oxide. .H-NMR (500 MHz, J6-DMSO) S 13.75 (s, 1H), 8.87 (d, 1H),8.54 (d, 1H), 8.21 (d, 1H), 7.85 (m, 1H), 7.77 (m, 1H), 7.58 (t, 1H), 7.41 (m, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 875781-17-2.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2006/15124; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52313-50-5, 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. 52313-50-5, name is Picolinimidamide. A new synthetic method of this compound is introduced below.

A mixture of N-methyl-4-(4-oxo-1-piperidyl)benzenesulfonamide (0.45 g, 1.67 mmol) andDMFDMA (2 mL) in acetonitrile (8 mL) was heated with stuffing at 90 C for 2 hrs. Theresulting reaction mixture was concentrated in vacuo and the residue was dissolved in EtOH (10 mL). To the solution was added pyridine-2-carboxamidine (0.15 g, 1.23 mmol) and potassium carbonate (034 g, 246 mrnol) successively. After being heated with stirring at 90 C overnight, the resulting reaction mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (20 mL) for three times. The combined organic layer was washed with brine, dried overanhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep-PLC to give Nmethyl-4- [2- (2-pyridyl)-7 , 8-dihydro-5H-pyrido [4,3-d]pyrimidin-6-yl]benzenesulfonamide (7 mg). ?H NMR (400MHz, CDC13): oe 8.87 (d, 1H), 8.80 – 8.70 (m, 1H), 8.53 (d, 1H), 7.89 (dt, 1H), 7.80 (d, 2H), 7.44 (ddd, 1H), 7.06 – 6.97 (m, 2H), 4.63 (s, 2H), 3.86 (t, 2H), 3.32 (t, 2H), 2.67 (s, 3H). MS obsd. (ESIj [(M+H)?i: 382.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52313-50-5, Picolinimidamide, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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. 113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, 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. Product Details of 113118-81-3

To a mixture of 5-bromopyridine-3-carbaldehyde (XXXVII) (6.00 g, 32.26 mmol, 1.0 eq), 3,3-difluoropyrrolidine (5.56 g, 38.71 mmol, 1.20 eq) and TEA (5.39 mL, 38.71 mmol, 1.2 eq) in DCE (200 mL) was stirred at room temperature for 30 min, then added sodium triacetoxyborohydride (10.25 g, 48.38 mmol, 1.50 eq) in one portion at room temperature under N2. The mixture was stirred at room temperature for 6 hours. TLC showed the reaction was complete. The reaction was quenched with IN NaOH (100 mL), extracted with DCE (100 mL x 2). The combined organic layers were washed with brine (100 mL), dried and concentrated. The residue was purified by silica gel chromatography (column height: 50 mm, diameter: 50 mm, 300- 400mesh silica gel, DCM/MeOH=30/l?20/l) to give 3-bromo-5-((3,3-difluoropyrrolidin-l- yl)methyl) pyridine (XXXIX): Yellow oil (8.00 g, 28.9 mmol, 89.5% yield). ‘H NMR (CDC13, 400 MHz) delta ppm 2.30 (spt, J=7.2Hz. 2H), 2.75 (t, J=6.8Hz, 2H), 2.91 (t, J=13.2Hz, 2H), 7.85 (s, IH), 8.45 (s, IH), 8.59 (d, J=2Hz, IH); ESIMS found for CioHiiBrF2N2 mlz 277.0 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 113118-81-3.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (299 pag.)WO2017/24015; (2017); 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. 115170-40-6, name is 5-Bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 115170-40-6

In a microwave vial are combined l-ieri-butyl-2-(5-methoxy-2-pyrazol-l-yl-phenyl)-5- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-benzimidazole (285 mg, 0.60 mmol), 5-bromo-2,3-dihydro-lH-pyrrolo[2,3-b]pyridine (100 mg, 0.50 mmol), potassium carbonate (140 mg, 1.0 mmol), and bis(di-ieri-butyl(4- dimethylaminophenyl)phosphine)dichloropalladium(II) (53 mg, 0.08 mmol) in toluene (3.0 mL) and water (0.30 mL). The reaction vial is sealed and stirred at 100 C for 4 hours in an oil bath. After this time the reaction is cooled and poured into water. The product is extracted into EtOAc (2x). The combined organics are dried (MgS04), filtered and concentrated. Purification via flash chromatography (12g silica gel, 0-5% MeOH/ CH2C12) affords the title compound (40 mg, 17%). LCMS (ESMS): m/z 465.20 (M++l)

The synthetic route of 115170-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; HAO, Ming-Hong; LIU, Weimin; LO, Ho-Yin; LOKE, Pui Leng; MAN, Chuk, Chui; MORWICK, Tina, Marie; NEMOTO, Peter, Allen; TAKAHASHI, Hidenori; TYE, Heather; WU, Lifen; WO2011/68821; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 79456-34-1, 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 79456-34-1, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

8.04 g (31.7 mmol) of 5-bromo-3-trifluoromethyl-pyridin-2-ylamine (preparation see Stage 1.3.2), 10.5 g (41.2 mmol) of 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1 ,3,2]dioxaborolanyl] (Aldrich), 9.62 g (95.1 mmol) of KOAc in 100 ml dioxane are degassed with argon for 15 min. Then 776 mg (0.951 mmol) of bis(diphenylphosphino)ferrocene dichloropalla-dium(ll)di-chloromethane (ABCR) are added and the mixture is degassed for 15 more minutes. The reaction mixture is heated at 1 15C for 8 h. After that time, the reaction mixture is filtered and the solvent evaporated. The residue is purified by simple filtration on silicagel (solvent system: t-butyl-methyl ether-EtOAc-NEt3 = 50:50:0.1 ) to yield the title compound as almost colorless solid. ES-MS: (M+1 ) = 289; TIc: Rf=O.77 in t-buthyl-methyl ether-EtOAc 1 :1.

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 79456-34-1, 5-Bromo-3-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; IMBACH, Patricia; MAH, Robert; STAUFFER, Frederic; WO2010/139747; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem