Day: April 14, 2022

Application of 89415-54-3, 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 89415-54-3, name is 5-Bromo-N2-methylpyridine-2,3-diamine. This compound has unique chemical properties. The synthetic route is as follows.

e. 4-[(7-bromo-4-methyl-3-oxo-3,4-dihydro-pyrido[2,3-b]-pyrazin-2-yl)methyl]-benzonitrile Prepared analogously to Example 7f from 3-amino-5-bromo-2-methylamino-pyridine and 3-(4-cyano-phenyl)-2-oxo-propionic acid in ethanol. Yield: 26.2% of theory, Rf value: 0.68 (silica gel; methylene chloride/ethanol/glacial acetic acid=4:1:0,01).

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 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6200976; (2001); B1;,
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 915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 915006-52-9

A solution of 6-bromo-2-iodo-pyridin-3-ylamine (as prepared in the previous step, 1.00 g, 3.35 mmol) in toluene (27 mL) and EtOH (13.5 mL) was treated with 2.0 M aq Na2CO3 (13.4 mL, 26.8 mmol) and 4,4-dimethyl-cyclohex-1-enylboronic acid (567 mg, 3.68 mmol). The mixture was degassed via sonication, placed under Ar, treated with Pd(PPh3)4 (271 mg, 0.234 mmol), and heated to 80 C. for 5 h. The cooled mixture was diluted with EtOAc (100 mL) and washed with water (2×50 mL). The combined aqueous layers were extracted with EtOAc (1×100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 50-g column with 10% EtOAc-hexane afforded 668 mg (71%) of 6-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-3-ylamine as a tan solid. 1H-NMR (CDCl3; 400 MHz): delta 7.06 (d, 1H, J=8.3 Hz), 6.85 (d, 1H, J=8.3 Hz), 5.95 (m, 1H), 3.86 (br s, 2H), 2.43-2.39 (m, 2H), 1.99-1.97 (m, 2H), 1.51 (t, 2H, J=6.4 Hz), 0.99 (s, 6H).

With the rapid development of chemical substances, we look forward to future research findings about 915006-52-9.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; DesJarlais, Renee Louise; Meegalla, Sanath K.; Wall, Mark; Wilson, Kenneth; US2007/249608; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 380380-64-3 ,Some common heterocyclic compound, 380380-64-3, molecular formula is C7H6BrN5, 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.

To a 5 -L, three-neck, round-bottom flask was charged 4 (200.0 g, 0.833 mol) followed by 1,4-dioxane (3 L, 15 vol). Crude compound 6 (361.2 g, 1.249 mol, 1.5 equiv.), Pd2(dba)3 (11.44 g, 0.0125 g, 0.015 equiv.), and PCy3 (7.0 g, 0.025 mol, 0.03 equiv.) was charged and degassed with nitrogen for 30 minutes. A solution Of K2CO3 (195.7 g, 1.7 equiv.) in water (800 mL, 4 vol) was charged, and the reaction was heated to 70 0C. The reaction was complete after 1 hour with 0.5 area % of 4 remaining. The reaction was cooled to 50 0C, and Darco G-60 (40 g, 0.2 wt) was added and stirred for 30 minutes. Celite 545 (40 g, 0.2 wt) was charged and then the reaction was filtered through Celite 545 (100 g, 0.5 wt) wetted with water (300 mL). The hot filtration into the water from the Celite caused precipitation of the product. Tetrahydrofuran (1.2 L, 6 vol) and brine (600 mL, 3 vol) were added, and the product re-dissolved at room temperature. The phase split was accomplished cleanly (Vmax = 28 volumes). The dioxane was concentrated and ethanol (1 L, 5 vol) was added and concentrated. Then the product was reslurried in ethanol: water (4: 1, 2 L, 10 vol) at 700C, cooled to room temperature over 3 hours, filtered and washed with ethanol (2 x 400 mL). Compound 7 was isolated in 87% yield (292.6 g) with a purity of 97.7 % (AUC) by HPLC analysis. The 1H NMR and 19F NMR indicated the presence of one compound. Pd analysis showed 135 ppm Pd was in the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,380380-64-3, its application will become more common.

Reference:
Patent; TRIUS THERAPEUTICS; COSTELLO, Carrie, A.; SIMSON, Jaqueline, A.; DUGUID, Robert, J.; PHILLIPSON, Douglas; WO2010/42887; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 914358-72-8, 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. 914358-72-8, name is 5-Bromo-3-chloro-2-methylpyridine. A new synthetic method of this compound is introduced below.

A 40-mL vial containing 5-bromo-3-chloro-2-methylpyridine (185 mg, 0.896 mmol, purchased from Synthonix Inc.), potassium acetate (264 mg, 2.69 mmol), bis(pinacolato)diboron (250 mg, 0.986 mmol), and 1,1′-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (36.6 mg, 0.045 mmol) was flushed with N2. Dioxane (4.5 mL) was added, and the orange slurry was stirred at 90 C. After 2.5 h, the resulting black slurry was cooled to rt, washed twice with brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford 3-chloro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine as a black oil that was used with further purification. m/z (ESI) 254.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,914358-72-8, 5-Bromo-3-chloro-2-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
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.89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine, molecular formula is C5H4ClFN2, molecular weight is 146.55, as common compound, the synthetic route is as follows.Recommanded Product: 89510-90-7

To a solution of 2-chloro-5-fluoropyridin-4-amine (500 mg) in acetic anhydride (5.0 mL) was added N,N-dimethyl-4-aminopyridine (4.2 mg), and the mixture was stirred at 80 C. for 4 hr. The reaction mixture was cooled to 0 C., saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (440 mg). MS(ESI+): [M+H]+ 189.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 76629-11-3, 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.76629-11-3, name is 3-((6-Chloropyridin-2-yl)amino)propanoic acid, molecular formula is C8H9ClN2O2, molecular weight is 200.6223, as common compound, the synthetic route is as follows.

B) 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one A mixture of N-(6-chloropyridin-2-yl)-beta-alanine (40 g) and Eaton’s Reagent (600 mL) was stirred at 75C for 3 hours. The reaction mixture was poured to ice water and basified to pH = 10 with sodium hydroxide, followed by extraction with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound. MS: [M+H]+ 182.8.

Statistics shows that 76629-11-3 is playing an increasingly important role. we look forward to future research findings about 3-((6-Chloropyridin-2-yl)amino)propanoic acid.

Reference:
Patent; Takeda Pharmaceutical Company Limited; ASANO, Yasutomi; KOJIMA, Takuto; KURASAWA, Osamu; WONG, Tzu-Tshin; HIRATA, Yasuhiro; IWAMURA, Naoki; SAITO, Bunnai; TANAKA, Yuta; ARAI Ryosuke; IMAMURA, Shinichi; YONEMORI, Kazuko; MIYAMOTO, Yasufumi; KITAMURA, Shuji; SANO, Osamu; (222 pag.)EP3287441; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 700811-29-6, 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 700811-29-6 as follows.

Step 2: 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde To a solution of 1-(2-chlorophenyl)ethanone (1.08 mL, 8.36 mmol) in AcOH (33 mL) was added 2-chloro-4-hydrazinopyridine (1.20 g, 8.36 mmol). The reaction mixture was allowed to stir at rt for 1 h and was then diluted with water. A white precipitate formed, and the mixture was extracted with EtOAc several times. The organic solutions were combined, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated.The residue was dissolved in DMF (15 mL) and added to a solution of phosphoryl chloride (1.56 mL, 16.7 mmol) in DMF (13 mL) which had been stirring at rt for 30 min. The reaction mixture was allowed to stir at 80 C. for 18 h and then at rt for 35 h. The mixture was diluted with water and extracted several times with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde (1.95 g, 73%). LCMS (AA): m/z=318 (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,700811-29-6, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 102645-33-0, Adding some certain compound to certain chemical reactions, such as: 102645-33-0, name is 2,5-Dichloroisonicotinaldehyde,molecular formula is C6H3Cl2NO, 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 102645-33-0.

(2) To be equipped with mechanical stirring, thermometer,After nitrogen substitution in the three-port reaction flask of the constant pressure dropping funnel,Add the raw materials 4a-1 (200mmol) in sequence,500.0ml tetrahydrofuran, start stirring, and cool down to -85 -90 ,Add 2mol / L n-butyllithium (210mmol) dropwise,The temperature during the dropping is maintained at -85 -90 , and the temperature is kept for 1h after the dropping is completed.A solution of the raw material 2,5-dichloropyridine-4-aldehyde (200 mmol) + 140.0 ml of tetrahydrofuran was added dropwise.After the dropwise addition, the temperature was kept for 0.5h, and the temperature was naturally raised to room temperature for 3h.The reaction solution was poured into 10% aqueous ammonium chloride solution, and extracted with 320.0 ml of toluene,Separate the liquid and extract the aqueous phase once with 320.0 ml of toluene,Combine the organic phases, wash twice with 260.0 ml of water, and separate.The organic phase is dried by adding 12g of anhydrous sodium sulfate and filtered,The organic phase is concentrated (-0.08 -0.09MPa, 55 65 ) to no avail,Add 150.0ml petroleum ether and stir for 0.5h, filter, rinse the filter cake with petroleum ether,Intermediate 4a-2 (150 mmol) was obtained with a yield of 75%.

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. 102645-33-0, 2,5-Dichloroisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanxi Laite Optoelectric Materials Co., Ltd.; Wu Xingzhi; Xue Zhen; Wang Jinping; (49 pag.)CN111004237; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-95-0, 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. 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: To a solution of 5-chloro-4-iodo-2-(trifluoromethyl)pyridine (18.2 g, 59.2 mmol) in diethylether (200 mL), at -78 C in a 1L 3 neck RBF, was added n-butyl lithium (1.6 M in hexane, 44.5 mL, 71.1 mmol). The resulting solution was stirred at that temperature for 10 minutes and ethyl-N-Boc-(S)-pyroglutamate (16.75 g, 65.2 mmol) in diethylether (130 mL) was added slowly, and the resulting solution was stirred at that temperature for 1 h. The reaction was stopped by the addition of saturated NH4C1 solution (150 mL) and extracted with EtOAc (2 x 250 mL).The organic layer was washed with water (2 x 150 mL), dried over anhydrous Na2S04 and concentrated to yield ethyl (S)-2-((tert-butoxycarbonyl)amino)-5-(5-chloro-2- (trifluoromethyl)pyridin-4-yl)-5-oxopentanoate which was carried forward to the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823221-95-0, 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; SHAO, Pengcheng Patrick; KRIKORIAN, Arto, D.; VACHAL, Petr; WO2015/17302; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To a mixture of 2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetic acid (34, 0.899 g, 3.21 mmol) in ethyl acetate (20 ml) was added 5-(trifluoromethyl)pyridin-3-amine (10, 0.520 g, 3.21 mmol), triethylamine (1.0 ml) and propylphosphonic anhydride (50 wt % solution in ethyl acetate, 2.51 ml, 4.22 mmol). The mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was suspended in a mixture of ethyl acetate and hexane. The solid precipitate was collected by filtration and washed with hexane. After drying, this provided 1.03 g of compound 46. MS ESI [M+H+]+=425.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

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