Month: April 2022

Electric Literature of 947179-03-5 , The common heterocyclic compound, 947179-03-5, name is Ethyl 4-bromo-6-methylpicolinate, molecular formula is C9H10BrNO2, 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.

A mixture of 4-bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester [CAS No. 947179-03-5] (1.22 g, 5.0 mmol), zinkcyanid (0.88 g, 7.0 mmol) and tetrakis-(triphenylphosphine)-palladium(0) (578 mg, 0.5 mmol) in DMF (15 ml) was stirred in a microwave oven for 15 minutes at 160 C. The mixture was poured into water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (50 ml) and dried (MgSO4). Removal of the solvent left a light yellow solid (1.74 g), which was further purified by flash chromatography on silica gel [heptan/ethyl acetate (20-80%)] to yield the title compound as a white solid (0.48 g, 50%), MS (ISP) m/e=191.2 [(M+H)+], mp 50 C.

The synthetic route of 947179-03-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jaeschke, Georg; Vieira, Eric; Wichmann, Juergen; US2010/227887; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 727356-19-6, Adding some certain compound to certain chemical reactions, such as: 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine,molecular formula is C6H5BrClN, 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 727356-19-6.

General procedure: 3-Bromo-4-nitro-1H-indazole 2 (1.0 g) and R1CH2Cl (0.8 g) were added to N,N-dimethylformamide (10 mL). Potassium carbonate (1.14 g) was added to the solution, and stirred at 25C for 24 hrs. The reaction mixture was extracted with ethyl acetate (20 mL, three times) and water (20 mL), and the organic layers thus obtained were pooled, dried over anhydrous magnesium sulfate, and subjected to vacuum filtration and vacuum distillation. The residue was purified using column chromatography to afford the desired compound (1.36 g).

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. 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kim, Yu-Yon; Choi, Jaeyul; Choi, Kyungjin; Park, Changhee; Kim, Young Hoon; Suh, Kwee Hyun; Ham, Young Jin; Jang, Sun Young; Lee, Kyu-Hang; Hwang, Kwang Woo; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 271 – 275;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 175204-82-7, 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.175204-82-7, name is Methyl 4-(trifluoromethyl)nicotinate, molecular formula is C8H6F3NO2, molecular weight is 205.134, as common compound, the synthetic route is as follows.

3-Isopropyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (Table 1, No. 81) 2 g of methyl 4-trifluoromethylnicotinate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0 C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of two hours and stirring was then continued at this temperature until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil. 1H-NMR (CDCl3, 300 MHz): d=1.41 (d, J=6.9 Hz, 6H), 3.22 (m, 1H), 7.78 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

Statistics shows that 175204-82-7 is playing an increasingly important role. we look forward to future research findings about Methyl 4-(trifluoromethyl)nicotinate.

Reference:
Patent; Hoechst Schering AgrEvo GmbH; US6699853; (2004); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1079179-12-6, name is 2-Chloro-3-fluoro-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H2ClFN2O2

To a solution of Compound 4 (3 g, 12.22 mmol, 1 eq) and 2-chloro-3-fluoro-5-nitropyridine (2.37 g, 13.44 mmol, 1.1 eq) in DMF (20 mL) was added K2CO3 (3.38 g, 24.44 mmol, 2.0 eq) in one portion at 16 C, followed by heating with stirring at 70 C for 2 h. The reaction mixture was poured into water, and the resulting solids were filtered. The filter cake washed with water (20 mL) and dried under vacuum to give the Compound 7 as a yellow solid (3.5 g, 68.1% yield). NMR (400 MHz, DMSO-d6) delta 9.43 (d, 1H), 9.17 (dd, 1H), 8.53 (s, 1H), 8.10 (d, 1H), 6.67 (s, 1H), 6.29 (d, 1H), 3.83 (s, 3H), 3.74 (s, 3H); MS (El) for C17H12FN3O6, found 374.0 (MH+).

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, 1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine.

Reference:
Patent; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 349-94-0, 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. 349-94-0, name is 5-Chloro-2-trifluoromethylpyridine. A new synthetic method of this compound is introduced below.

Step C 5-chloro-4-iodo-2-(trifluoromethyl)pyridine Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-chloro-2-(trifluoromethyl)pyridine (as prepared in the previous step, 5 g, 27.62 mmol, 1.00 equiv) in tetrahydrofuran (50 mL). LDA (3 g, 28.04 mmol, 1.05 equiv, as a THF solution) was added dropwise with stirring at -78 C. The resulting solution was stirred for 30 min at -78 C. A solution of I2 (7.4 g, 29.13 mmol, 1.05 equiv) in tetrahydrofuran (10 mL) was added dropwise with stirring at -78 C. The reaction mixture was stirred for an additional 2 h at -78 C., quenched with 15 mL of Na2S2O3(1M) and diluted with 100 mL of water. The resulting mixture was extracted with 3*50 mL of ether. The combined organic layers were washed with 50 ml brine, dried (Na2SO4), and concentrated under vacuum. The residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (0:1), yielding 5-chloro-4-iodo-2-(trifluoromethyl)pyridine as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,349-94-0, 5-Chloro-2-trifluoromethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Zhang, Xuqing; Sui, Zhihua; Lanter, James C.; US2011/306592; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, 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, blongs to pyridine-derivatives compound. COA of Formula: C10H11BrClNO2

Cs2CO3 (4.1 g, 12.6 mmol) and 4A sieves were dried under high vacuum at 1500C for 6 to 10 hours before the start of the reaction. Once cooled down, compound 121A (0.736 g, 2.53 mmol) and compound IB (1.62 g, 3 mmol) were transferred to the reaction vessel and the atmosphere was purged with nitrogen. 12 mL of anhydrous DMA were then added and the reaction was stirred at 1200C for 12 hours. The cooled reaction mixture was then diluted with ethyl acetate and citric acid 10%. The organic phase was washed three times with citric acid, once with water and brine, and dried over Na2SO4. Concentration of the organic phase afforded an orange film/foam. Purification on Flash Master (SiO2, ethyl acetate/petroleum ether 0:100 to 40:60) afforded a the product 121B as a white solid (1.15 g, 80 % yield): 1H NMR (300 MHz, CDCl3) delta 7.86 (m, IH), 7.71 (d, IH), 7.60 (d, IH), 7.50 (m, IH), 7.42-7.22 (m, 5H), 6.67 (d, IH), 4.99 (s, 2H), 3.95 (t, 2H), 3.01 (t, 2H), 1.56 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1235036-15-3, its application will become more common.

Reference:
Patent; GENENTECH, INC.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; ABBOTT LABORATORIES; BAELL, Jonathon, Bayldon; BUI, Chinh, Thien; COLMAN, Peter; CZABOTAR, Peter; DUDLEY, Danette, A.; FAIRBROTHER, Wayne, J.; FLYGARE, John, A.; LASSENE, Guillaume, Laurent; NDUBAKU, Chudi; NIKOLAKOPOULOS, George; SLEEBS, Brad, Edmund; SMITH, Brian, John; WATSON, Keith, Geoffrey; ELMORE, Steven, W.; HASVOLD, Lisa, A.; PETROS, Andrew, M.; SOUERS, Andrew, J.; TAO, Zhi-Fu; WANG, Le; WANG, Xilu; DESHAYES, Kurt; WO2010/80503; (2010); 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.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.Quality Control of N-(4-Bromopyridin-2-yl)acetamide

To the solution of (R)-tert-butyl methyl(3 -methyl- 1 -(5 -(trimethylstannyl)- 1H- benzo[d]imidazol-2-yl)butyl)carbamate (600 mg, 1.25 mmol) in DMF (6 mL), N-(4- bromopyridin-2-yl)acetamide (284 mg, 1.32 mmol), TBAB (530 mg, 1.65 mmol) and K2C03 (430 mg, 3.11 mmol) were added. Nitrogen gas was bubbled through the stirred solution for 5 min. Pd (PPh3)2Cl2 (73 mg, 0.378 mmol) was added and nitrogen purging through the solution was continued for another 5 min. The reaction mixture was then heated at 90 C for overnight. The reaction mixture was cooled to room temperature, concentrated under reduced pressure to remove solvents and diluted with water. The aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (50 mL). The organic layer was dried over Na2S04, filtered and concentrated under reduced pressure to afford the title compound (330 mg, 0.73 mmol, 59% yield) as solid. LCMS (ESI) m/e 450.2[(M-H)~, calcd for C25H32N5O3, 450.26]; LC/MS retention time (method C): tR = 1.71 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1241752-31-7 ,Some common heterocyclic compound, 1241752-31-7, molecular formula is C8H10BrNO2, 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.

a. Preparation of Compound To a solution of intermediate 2c (2-ethoxy-3-methoxy-5-bromopyridine) (140 mg, 0.5 mmol) in 4 ml dioxane: water (3:1) was added 4-(fluoromethyl)phenylboronic acid (104 mg, 0.75 mmol) and potassium carbonate (138 mg, 1.0 mmol). The resulting mixture was degassed for 15 minutes after which Pd (PPh3)4 (60 mg, 0.06 mmol) was added and the mixture was further degassed for 15 minutes. The reaction mixture was then heated at 100 C for 12 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and was washed with saturated sodium bicarbonate, followed by brine. The organic phase was dried with sodium sulfate and concentrated under reduced pressure to afford crude product which was purified by ISCO flash chromatography using 10%- 100% EtOAC in hexane to afford 1 19 mg product pure product (yield: 96%); lU NMR (300 MHz, CDC13) delta: 7.84(s, 1H), 7.44 (m, 2H), 7.14-7.08 (m, 3H), 4.46 (qt, J = 7.2 Hz, 2H), 3.88 (s, 3H), 1.44 (qt, J= 7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1241752-31-7, its application will become more common.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LAVOIE, Edmond J.; BAUMAN, Joseph David; PARHI, Ajit; SAGONG, Hye Yeon; PATEL, Disha; ARNOLD, Eddy; DAS, Kalyan; VIJAYAN, Suyambu Kesava; WO2014/43252; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 117846-58-9, 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. 117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 3 (1.60 g, 6.04 mmol) in anhydrous THF (50 mL) was added dropwise a 2.5 molL-1 solution of n-BuLi inhexane (2.30 mL, 5.74 mmol) at 195 K. The reaction was stirred for 30 minat this temperature, a solution of 4 (1.78 g, 5.49 mmol) in THF (2 mL) was added. Thereaction solution was stirred for 1 h at this temperature. The reactionwas allowed to warm to room temperature, and quenched with water (15 mL). Theproduct was extracted with diethyl ether. The organic layers were combined,dried over anhydrous Na2SO4, filtered, and concentratedin vacuo. Column chromatography on Al2O3 (hexane)afforded diarylethene 1o (1.26 g, 46.8%)as a colorless crystal, mp. 146-147 C; MS m/z (M+) 492.1 (+H); Anal.Calcd for C21H14BrF6NO:Calcd C, 51.45; H, 2.88; N, 2.86. Found C, 51.61; H, 2.99; N, 2.96; 1HNMR (400 MHz, CDCl3, TMS): delta 7.49-7.51 (m, 1H), 7.37 (m, 1H), 7.28 (s, 1H,pyridine-H), 7.23-7.24 (m, 2H), 2.33 (s, 3H, -CH3), 2.22 (s, 3H, -CH3),1.88 (s, 3H, -CH3). 13C NMR (100 MHz, CDCl3,TMS): delta 156.63, 154.09, 141.72, 141.01, 138.20, 136.15, 132.57,124.53, 123.59, 119.93, 118.86, 110.99, 104.19, 21.68, 17.44, 13.25. IR (KBr, nu, cm-1):3128, 1598, 1398, 1272, 1195, 1122, 1076, 1006, 979, 858, 829, 806, 740.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,117846-58-9, its application will become more common.

Reference:
Article; Zheng, Chunhong; Pu, Shouzhi; Liu, Gang; Chen, Bing; Tetrahedron Letters; vol. 54; 51; (2013); p. 7024 – 7028;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 866775-18-0, 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.866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, molecular weight is 299.05, as common compound, the synthetic route is as follows.

Step 1: 3-Amino-6-cyclopropyl-5-(trifluoromethyl)picolinic acidA microwave vial was charged with amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A4) (0.5 g, 1.754 mmol), cyclopropylboronic acid (0.753 g, 8.77 mmol), and 1,1’Bis(diphenylphosphosphino) ferrocene palladium dichloride (0.143 g, 0.175 mmol). The mixture was taken up as a solution in THF (6 ml) and flushed with N2, sealed and heated using microwave radiation at 150 C. for 20 minutes. The reaction mixture was filtered through Celite (filter material) and washed through with EtOAc (20 ml). The filtrate was partitioned between EtOAc (30 ml) and water (50 ml). The phases were separated and the organic portion was washed with brine (30 ml), dried over MgSO4, filtered and concentrated under vacuum.The crude material was taken up in EtOAc (20 ml) and dry loaded onto silica (2-3 g). Material then purified on the Combiflash Rf Teledyne ISCO System 100% Isohexane to 60% EtOAc:Isohexane to afford semi pure material which was used without further purification.

Statistics shows that 866775-18-0 is playing an increasingly important role. we look forward to future research findings about Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate.

Reference:
Patent; NOVARTIS AG; US2011/230483; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem