Tag: M.W:200-300

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 290307-40-3, name is 2-(5-Bromopyridin-2-yl)propan-2-ol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 290307-40-3

In a 2 L round-bottomed flask was mixed 2,5-dibromopyridine (54 g, 228 mmol) in toluene (600 ml) to give a colorless solution. The reaction was cooled to -78 C. and n-Butyllithium 2.5M hexanes (100 ml, 251 mmol) was added at a rate that the temperature did not exceed -70 C. The reaction was stirred for 30 minutes and then acetone (20.08 ml, 274 mmol) was added quickly. The reaction was stirred for 30 minutes and then quenched with saturated ammonium chloride. The organic layer was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure. The crude residue was purified by column chromatography 20-50% ethyl acetate/heptane to give 42.5 g of 2-(5-bromopyridin-2-yl)propan-2-ol in 86% yield.In a 1 L round-bottomed flask was mixed compound 2-(5-bromopyridin-2-yl)propan-2-ol (10 g, 46.3 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (11.87 g, 50.9 mmol) in dioxane (300 ml). To this was added saturated sodium bicarbonate (150 mL). The reaction mixture was degassed via purging with a stream of nitrogen and then Pd(PPh3)4 (2.67 g, 2.314 mmol) was added. The mixture was heated to reflux becoming very thick then finally going into solution. The reaction was heated for 2 hours, cooled to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure to give 2-(5-(5-amino-2-methylphenyl)pyridin-2-yl)propan-2-ol.The crude product from above was dissolved in dioxane (30 mL) and cooled to 0 C. Sulfuric acid was added to the solution through an addition funnel with manual stirring necessary at the beginning of addition, finally going to solution. The reaction was allowed to exotherm up to 30 C. and stirred for 30 minutes. Upon completion of the reaction as determined by LC/MS, the reaction was poured onto ice, extracted with ethyl acetate (2×200 mL) and the pH of the aqueous was adjusted to 9-10 by addition of 50% sodium hydroxide solution. The mixture was then extracted with ethyl acetate, the organic was washed with brine and dried over sodium sulfate. After removal of solvent the crude product was isolated by column chromatography eluting 0-100% ethyl acetate/heptane to give 4-methyl-3-(6-(prop-1-en-2-yl)pyridin-3-yl)aniline. Yield 9 g, 86% over 2 steps.4-Methyl-3-(6-(prop-1-en-2-yl)pyridin-3-yl)aniline (9 g, 40.1 mmol) was dissolved in ethanol (100 mL) and 10% palladium on carbon (0.5 g) was added. The mixture was hydrogenated at 30 psi for 2 hours. Filtration and concentration of the product afforded clean 3-(6-isopropylpyridin-3-yl)-4-methylaniline. Yield 8 g, 88%

With the rapid development of chemical substances, we look forward to future research findings about 290307-40-3.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1160791-13-8, Adding some certain compound to certain chemical reactions, such as: 1160791-13-8, name is 2-Amino-6-bromothiazolo[5,4-b]pyridine,molecular formula is C6H4BrN3S, 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 1160791-13-8.

To a solution of 6-bromothiazolo[5,4-b]pyridin-2-amine IV (1.30 g, 5.55 mmol) in 1 ,4- dioxane (20.0 mL) was added ethylisocyanate (2.19 mL, 27.07 mmol) and the resulting reaction mixture was heated to 8O0C for 8 h. After the completion of the reaction (TLC monitoring), 1 ,4.-dioxane was distilled off followed by co-distillation with n-hexane (2 times). The residue was then stirred with water at 9O0C for 2h followed by filtration to obtain the desired product that was further washed with hot water and then dried. The residue was finally washed with ether to obtain the desired product (1.40 g, 83%). 1H NMR (400MHz, DMSO-d6): delta 1.10 (t, J= 7.20 Hz, 3H), 3.20 (quintet, J= 7.20 Hz, 2H), 6.76 (br s, 1 H), 8.24 (d, J= 2.0 Hz, 1 H), 8.45 (d, J= 2.0 Hz1 1 H) and 11.05 (br s, 1 H).

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. 1160791-13-8, 2-Amino-6-bromothiazolo[5,4-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROLYSIS LTD; WO2009/74812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8, 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. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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.

General procedure: 5.1.1 General procedure A (for synthesis of compounds 1-19). To 2-bromoacetylpyridine hydrobromide (1.0 equiv) in anhydrous ethanol (5 mL) was added the corresponding thiourea (1.0 equiv, 0.2 g) and the reaction mixture refluxed for 4 h. After cooling to ambient temperature the reaction mixture was poured into water. The pH of the mixture was adjusted to pH 8 with concentrated aqueous NH4OH and the mixture stirred for 2 h. The precipitate was filtered, washed with ethanol and dried to afford the title compound.

According to the analysis of related databases, 17570-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meissner, Anja; Boshoff, Helena I.; Vasan, Mahalakshmi; Duckworth, Benjamin P.; Barry III, Clifton E.; Aldrich, Courtney C.; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6385 – 6397;,
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

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

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

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

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

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. 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, 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. SDS of cas: 718608-10-7

Sodium hydride (800mg, 60% dispersion in mineral oil, 20MMOL) and imidazole (54mg, 0. 8MMOL) were added portionwise to a cooled (-15C) solution of the acid from preparation 37 (960mg, 4MMOL) in tetrahydrofuran (40ML) and the solution stirred for 1 hour. A suspension of the bromide from preparation 40 (1.28g, 4. 8MMOL) and N-methyl morpholine (535mg, 5. 3MMOL) in TETRAHYDROFURAN (10M .) was added so as to maintain the temperature BELOW-1 5C, and the reaction then stirred for a further 2 hours. The reaction was allowed to warm to room temperature and stirred for a further 18 hours. The mixture was then basified to pH 11, washed with ethyl acetate, carefully acidifed to pH 5 and extracted with ethyl acetate. These combined organic solutions were washed with brine, dried (MGS04) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using DICHLOROMETHANE : methanol (94: 6) as eluant, and the product triturated with ether to afford the title compound, 177mg ;’H NMR (CDC13, 400MHZ) 8 : 1.42 (s, 9H), 2.62-2. 80 (m, 5H), 3.64 (m, 2H), 4.18 (m, 1 H), 4.60 (s, 2H), 5.50 (d, 1 H), 7.40 (d, 1 H), 7.83 (d, 1 H), 8.62 (s, 1 H) ; LRMS: M/Z (ES-) 323 [M-H]-.

With the rapid development of chemical substances, we look forward to future research findings about 718608-10-7.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/56750; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1186194-46-6 , The common heterocyclic compound, 1186194-46-6, name is 5-Bromo-6-methoxynicotinic acid, molecular formula is C7H6BrNO3, 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.

(5-bromopyridin-2-yl) ((2S) -2- (4-chlorophenyl) piperazin- 1 – yl) methanone hydrochloride(200 mg),5-Bromo-6-methoxynicotinic acid (130 mg),HATU (250 mg),Triethylamine (0.15 ml) and DMF (3 ml)Was stirred at room temperature for 2 hours.The mixture was extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate) and silica gel column chromatography (NH, hexane / ethyl acetate) to give the title compound (223 mg).

The synthetic route of 1186194-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MIZOJIRI, RYO; CARY, DOUGLAS ROBERT; HIRAYAMA, TAKAHARU; ITO, MASAHIRO; TANAKA, TOSHIO; IMAEDA, YASUHIRO; SASAKI, SHIGEKAZU; TAKAMI, KAZUAKI; FUKUDA, KOICHIRO; KAMAURA, MASAHIRO; MORISHITA, NAO; (133 pag.)JP2017/222626; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem