Category: pyridine-derivatives

Synthetic Route of 3678-62-4 ,Some common heterocyclic compound, 3678-62-4, molecular formula is C6H6ClN, 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 g of 2-chloro-4-methylpyridine are dissolved in 30 ml of CH3CN and a mixture of AIBN (3 g) and NCS (30 g) is added. The resulting mixture is refluxed for 4 hours. After removing the solvent, the crude product is further purified by distillation (boiling point: 70 C., 20 mtorr)

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. 3678-62-4, 2-Chloro-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2004/248884; (2004); 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, 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 5-(Trifluoromethyl)pyridin-3-amine

To a mixture of 2-(4-bromo-2,5-difluoro-phenyl)acetic acid (9, 2.16 g, 8.60 mmol), 5-(trifluoromethyl)pyridin-3-amine (10, 1.39 g, 8.57 mmol) and pyridine (2.09 ml, 25.8 mmol) in ethyl acetate (85 ml) was added slowly propylphosphonic anhydride (50 wt % solution in ethyl acetate, 10.1 ml, 17.2 mmol). The reaction mixture was allowed to stir at room temperature for 3 hours. The reaction was diluted with ethyl acetate and was washed with saturated aqueous ammonium chloride, water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to provide 3.29 g (97% yield) of compound 11 that was used in the next step without further purification. MS ESI [M+H+]+=397.05.

With the rapid development of chemical substances, we look forward to future research findings about 112110-07-3.

Reference:
Patent; Plexxikon Inc.; Lin, Jack; Ibrahim, Prabha N.; Albers, Aaron; Buell, John; Guo, Zuojun; Pham, Phuongly; Powers, Hannah; Shi, Songyuan; Spevak, Wayne; Wu, Guoxian; Zhang, Jiazhong; Zhang, Ying; (132 pag.)US2017/267660; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, 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, Computed Properties of C7H6FNO, blongs to pyridine-derivatives compound. Computed Properties of C7H6FNO

To a stirred solution of 3-fluoro-4-acetylpyridine (5.3 g, 38.1 mmol) in glacial acetic acid (14 mL) and 48% hydrobromic acid (5.3 mL), bromine (2 mL, 38 mmol) in glacial acetic acid (5.3 mL) was added slowly and dropwise. After addition, the solution was stirred at 60 C. for 2.5 h then it was cooled down and ethylacetate (70 mL) was added. After 30′ stirring the mixture was filtered and the solid was washed thoroughly with ethylacetate and dried. The title compound was obtained in 82% yield (9.4 g). 1H NMR (DMSO-d6/400 MHz) delta ppm 4.88 (s, 2 H) 7.83 (dd, 1 H) 8.62 (dd, 1 H) 8.81 (d, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142414; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1019021-85-2, 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.1019021-85-2, name is 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5FN2O2, molecular weight is 180.1359, as common compound, the synthetic route is as follows.

Oxalyl chloride (10 mL, 1 10 mmol) was added dropwise to a stirred suspension of 6- fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (24b) (2 g, 1 1 mmol) and catalytic amounts of DMF in dichloromethane (20 mL). After 5 hours, the solvent was evaporated and the solid was suspended in dry DCE (20 mL) and added to a stirred solution of 3- amino-4-methylbenzonitrile (1 .45 g, 1 1 mmol) and DIEA (6 mmol) in DCE (1 0 mL) at 0 C. After the addition, the reaction was heated at 60 C for 5 hours. The mixture was subjected to standard aqueous work and silica purification to give N-(5-cyano-2- methylphenyl)-6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (39) as a solid. 1 H NMR (400MHz, c/6-DMSO) delta 10.14 (s, 1 H), 9.45 (dd, J = 5.2, 2.0 Hz, 1 H), 8.62 (s, 1 H), 7.90 – 7.87 (m, 2 H), 7.68-7.63 (m, 1 H), 7.53 (d, J = 8.0 Hz, 1 H), 2.37 (s, 3H). MS m/z 295.1 (M+1 ) +. NH2OH (5 mL, 16.1 mmol) was added in one portion to a stirred suspension of N-(5- cyano-2-methylphenyl)-6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (39) (0.95 g, 3.23 mmol). The resulting suspension was heated at 60 C overnight and then cooled to 0 C. The product, (Z)-6-fluoro-N-(5-(N’-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1 ,2- a]pyridine-3-carboxamide (40) was collected by filtration. MS m/z 328.1 (M+1 ) +.

Statistics shows that 1019021-85-2 is playing an increasingly important role. we look forward to future research findings about 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62150-46-3, 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 62150-46-3, name is 4-Bromopicolinamide. This compound has unique chemical properties. The synthetic route is as follows.

The flask was charged with (2-(2-chlorophenyl)-8-methylquinolin-3-yl)methan- amine (100.0 mg, 0.354 mmol), obtained from A-1216 US PSP, procedure D, 4- bromopicolinamide (92 mg, 0.460 mmol), diisopropylethylamine (0.080 ml, 0.460 mmol) and 1-butanol (2.0 ml ) and sealed. The mixture was subjected to microwave at 180C for 4hrs. After cooled to room temperature, the mixture was concentrated, and the residue was diluted with MeOH. The solution was purified by HPLC, 25%-45% of B in 35min. The collected fractions were concentrated and dissolved in CH2Cl2, neutralized by washing with aq. NaHCO3. The CH2Cl2 layer was dried, concentrated and gave 4-((2-(2-chlorophenyl)-8-methylquinolin- 3-yl)methylamino)picolinamide, 1H-NMR (MeOD) delta 8.21 (s, 1 H), 8.01(d, J= 5.6 Hz, IH), 7.71 (d, J= 8.0 Hz, IH), 7.41-7.62 (m, 6 H), 7.20 (d, J= 2.4 Hz, IH), 6.50 (dd, J= 5.6,2.4 Hz, IH) 4.42 (d, J= 11.0 Hz, IH), 4.27 (d, J= 11.0 Hz, IH), 2.73 (s, 1 H). Mass Spectrum (ESI) m/e = 403.1 (M + 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 62150-46-3, 4-Bromopicolinamide.

Reference:
Patent; AMGEN INC.; WO2008/118455; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 124236-37-9 ,Some common heterocyclic compound, 124236-37-9, molecular formula is C8H6F3NO2, 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.

Intermediate A-28A: tert-Butyl (2-methoxy-6-(5-(trifluoromethyl)picolinoyl)phenyl)carbamate [0346] tert-butyl 2-methoxyphenylcarbamate (443.3 mg, 1.986 mmol) in ether (5 mL) under N2 was added t-BuLi (2.6 mL, 4.42 mmol). The reaction mixture was stirred for 2 h, and then cooled to -78 C. To the reaction mixture was added a solution of methyl 5-(trifluoromethyl)picolinate (501.3 mg, 2.44 mmol) in ether (10 mL) dropwise via cannula over 5 min. After 2 h, the reaction mixture was warmed to room temperature, stirred for an additional hour, and then the reaction was quenched by the addition of water with vigorous stirring. The reaction mixture was diluted with EtOAc, the organic phase was separated, washed with sat NaCl then dried (Na2SO4), filtered and concentrated to yield a yellow solid. The residue was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, 0% to 100% solvent A/B=hexane/EtOAc, REDISEP SiO2 40 g) to obtained Intermediate A-28A (546.8 mg, 69.5% yield)) as a yellow solid: 1H NMR (400 MHz, chloroform-d) delta ppm 8.83-8.88 (1H, m), 8.24 (1H, d, J=8.4Hz), 8.07 (1H, dd, J=8.4, 1.8 Hz), 7.25 (1H, d, J=1.5 Hz), 7.18-7.24 (1H, m), 7.09 (1H, dd, J=8.0, 1.7 Hz), 6.95 (1H, s), 3.93 (3H, s), 1.25 (9H, s).

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. 124236-37-9, Methyl 5-(trifluoromethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gavai, Ashvinikumar V.; DeLucca, George V.; O’Malley, Daniel; Gill, Patrice; Quesnelle, Claude A.; Fink, Brian E.; Zhao, Yufen; Lee, Francis Y.; US2014/87992; (2014); 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, molecular formula is C6H5BrClNO, 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. Computed Properties of C6H5BrClNO

Step B: 6-Chloro-4-methoxypyridine-3-carbonitrile: A solution of 5-bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added successively. The resulting suspension was stirred at 95 C for 12 h under nitrogen. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.

With the rapid development of chemical substances, we look forward to future research findings about 880870-13-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alex; SUZUKI, Takao; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda K.; WO2015/96035; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77199-09-8, 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 77199-09-8 as follows.

General procedure: A mixture 2a or 2b (1 g, 1 equiv.), anappropriate pinacol boronate ester (1.2 equiv.), [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex withdichloromethane (10 mol %), cesium carbonate (2.0 equiv.), 1,4-dioxane (8 ml) and water (4 ml) was sealed in a 20 ml microwavereaction vial (Biotage). The vial was irradiated in a microwaveapparatus at 110 C, normal absorption for 30-90 min. The reactionmixture was cooled to room temperature and work up was performedas described in method 1 to obtain the esters 4b-i.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77199-09-8, its application will become more common.

Reference:
Article; Tung, Truong Thanh; Jakobsen, Tim Holm; Dao, Trong Tuan; Fuglsang, Anja Thoe; Givskov, Michael; Christensen, S°ren Br°gger; Nielsen, John; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1011 – 1020;,
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. 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine, the common compound, a new synthetic route is introduced below. name: 2,6-Dimethyl-3-hydroxypyridine

Example 66; (3R)-1-{2-[(2,6-Dimethylpyridin-3-yl)oxy]ethyl}-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide (Isomer 1); a) 3-(2-Bromoethoxy)-2,6-dimethylpyridine; 2,6-Dimethylpyridin-3-ol (2 g) in dry DMF (20 mL) under nitrogen was treated with sodium hydride (1.234 g). After the initial effervescence ceased 1,2-dibromoethane (6.10 g) was added in one portion causing an exotherm to 40 C. The mixture was stirred at room temperature overnight, diluted with water (100 mL), and the products extracted into ether (3×75 mL). The dried extracts were concentrated to dryness, and the residue purified on silica gel eluting with ether/dichloromethane (1:1). The subtitled compound was isolated as an oil (1.2 g).1H NMR (400 MHz, CDCl3) delta 6.98 (1H, d), 6.92 (1H, d), 4.26 (2H, t), 3.65 (2H, t), 2.47 (6H, d).

The synthetic route of 1122-43-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ford, Rhonan; Mete, Antonio; Millichip, Ian; Teobald, Barry; US2010/113510; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1207625-29-3, 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. 1207625-29-3, name is 5-Bromo-6-fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4BrFN2, 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.

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of the commercially available 5-bromo-6-fluoro- 1H-pyrrolo[2,3-bjpyridine (CAS, 1190321-99-3, 15 g, 69.76 mmol, 1.00 equiv) in N,Ndimethylformamide (150 mL). This was followed by the addition of sodium hydride (4.2 g, 175.00 mmol, 1.50 equiv), in portions at 0 degree. After 0.5 h stirring, to this was added SEM-Cl (14 g, 84.34 mmol, 1.20 equiv) dropwise with stirring at 0 degree. The resulting solution was allowed to react, with stirring, for an additional 3 h at room temperature. The reaction was then quenched by the addition of 300 mL of water. The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:1-1:10). This resulted in 15 g (62%) of 5-bromo-6-fluoro-1-[[2- (trimethylsilyl)ethoxyj methylj -1 H-pyrrolo [2,3 -bjpyridine as yellow oil. H-NMR (CDC13, 300 MHz) 6: 8.19 (d, J=8.7 Hz, 1H), 7.37 (d, J=3.6 Hz, 1H), 6.54 (d, J=3.6 Hz, 1H), 5.64 (s, 2H), 3.58 (t, J=8.1 Hz, 2H), 0.98-0.93 (t, J=8.1 Hz, 2H), 0.00 (s, 9H).

According to the analysis of related databases, 1207625-29-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem