Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 16545-68-9, Cyclopropanol, 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, Formula: C3H6O, blongs to alcohols-buliding-blocks compound. Formula: C3H6O

A mixture of 2-bromo-6-fluoropyridine (371 mg, 2.1 mmol) and cyclopropanol (350 mg, 6.0 mmol) in NMP (6 mL) was stirred for 5 minutes at 0 oC. Then to the solution was added dropwise a solution of t-BuOK in THF (1M, 0.6 mL, 0.6 mmol) at 0 oC. After addition, the reaction mixture was warmed to RT and stirred for 2 h. The reaction mixture was poured into a mixed solvent of PE/EA/water (50 mL/50mL/100 mL). The organic layer was separated, washed with 5% of LiCl aqueous solution (20 mL), dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column (5% ~ 10% EA/PE) to afford 2-bromo-6-cyclopropoxypyridine (374 mg, 83%) as a colorless oil. LC- MS m/z: 216&218 [M+H]+. Purity (214 nm): 99.6%.

The synthetic route of 16545-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GREENLEE, William, J.; GOOD, Andrew, C.; (309 pag.)WO2017/176961; (2017); A1;,
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Related Products of 23783-42-8, 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 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: [chloromethyl 2,5,8,11-tetraoxatridecan-13-yl carbonate] To a stirred solution of chloromethyl carbonochloridate (2.6 g, 20 mmol) in dichloromethane (40 mL) was added a mixture of 2,5,8,11-tetraoxatridecan-13-ol (4.16 g, 20 mmol) and triethylamine (2 g, 20 mmol) in dichloromethane (5 ml) dropwise at 0 C. The resulting reaction mixture was stirred at 0 C. for 0.5 hour. TLC showed the reaction was completed. The reaction mixture was partitioned between tert-Butyl methyl ether (100 ml) and water (60 ml). The organic layer were collected, washed with brine (50 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel flash chromatography (eluted with 30% ethyl acetate in hexane) to afford chloromethyl 2,5,8,11-tetraoxatridecan-13-yl carbonate (2.2 g, yield 35.2%) as colorless oil. 1H NMR (400 MHz, CDCl3): delta 3.38 (s, 3H), 3.54-3.56 (m, 2H), 3.64-3.66 (m, 10H), 3.74-3.76 (m, 2H), 4.36-4.38 (m, 2H), 5.74 (s, 2H).

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 23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Hornberger, Keith R.; Snyder, Lawrence B.; Zimmermann, Kurt; Wang, Jing; Berlin, Michael; Crews, Craig M.; Dong, Hanqing; (605 pag.)US2018/99940; (2018); A1;,
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Electric Literature of 6351-10-6 , The common heterocyclic compound, 6351-10-6, name is 2,3-Dihydro-1H-inden-1-ol, molecular formula is C9H10O, 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.

DMAP (143.8 mg, 1.25 mol) and acetic anhydride (1185.6 L,12.48 mmol) were added to a rac-indanol (rac-2), 500 mg,4.16 mmol) solution in dichloromethane (40 mL). The reaction wasstirred at room temperature during 4 h and after that time, thesolvent was evaporated under reduced pressure. The resultingcrude was purified by flash chromatography on silica gel (5-95%EtOAc/hexane) to afford the desired rac-indanyl acetate (rac-3) asa yellow liquid in 80% yield.

The synthetic route of 6351-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Mattos, Marcos Carlos; De Fonseca, Thiago Sousa; Da Silva, Marcos Reinaldo; De Oliveira, Maria Da Conceicao Ferreira; De Lemos, Telma Leda Gomes; De Marques, Ricardo Araujo; Applied Catalysis A: General; vol. 492; 1; (2015); p. 76 – 82;,
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Application of 1562-00-1, 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. 1562-00-1, name is Sodium isethionate, molecular formula is C2H5NaO4S, 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.

Reaction product V, [C1impd]2[SO4] (3.166 g, 8.74 mmol) was dissolved in 2:1 alcohol-water (30 mL), whereupon a prepared solution of sodium isethionate (2.592 g, 17.50 mmol) in 2:1 alcohol-water (18 mL) was added to it with stirring. The resulting slurry was stirred for about 2 h, whereupon it was suction filtered, and the filtrate was concentrated as far as feasible by rotary evaporation. The residue was taken up in methanol (25 mL) and loaded onto an about 12-g column of 230-400 mesh silica gel previously packed in methanol.As in Example 3, the methanolic solution of crude [C1impd][ise] was pushed down to the level of the top of the silica gel bed with air pressure while the column issue was collected in a 250-mL round bottom flask; the flask previously containing the crude product was rinsed with methanol (25 mL) and the rinse methanol was similarly loaded and pressed down while the column issue was collected on top of the first fraction. The rinsing process was repeated once before the silica gel column was washed down with fresh methanol (125 mL), all the while collecting the column issue on top of the accumulated methanol solution. The combined methanolic fractions were concentrated by rotary evaporation to produce purified [C1impd][ise] (4.122 g, 15.96 mmol, 91%) as an ionic liquid. The ionic liquid of Example 11 slowly solidified at ambient conditions. Specifically, it was freely liquid when contained in a flask immersed in an 80 C. water bath; it remained liquid for several hours after it was removed from the water bath. Thereafter, several regions of the liquid began to slowly solidify independently of each other, and after about 1 day, the IL had turned thoroughly solid under ambient conditions.

According to the analysis of related databases, 1562-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FLUIDIC, INC.; US2012/321967; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 162744-59-4, (4-Bromo-2,6-difluorophenyl)methanol, 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, 162744-59-4, blongs to alcohols-buliding-blocks compound. name: (4-Bromo-2,6-difluorophenyl)methanol

General synthetic method 2: Borylation of arylbromides and subsequent Suzuki coupling with 5-bromopyrrolo[2,l-f][l ,2,4]- triazine derivatives without isolation of the intermediate arylboronic acid or ester: Arylbromide D (about 0.5 mmol) is dissolved in DMF (3 mL) in a microwave reactor vessel, argon is bubbled through the solution for 5 min, and [l ,l’-bis(diphenylphosphino)ferrocene]dichloro- palladium(II)-dichloromethane complex (0.1 equivalents), potassium acetate (3 equivalents) and bis(pinacolato)diboron (1.2 equivalents) are added. The vessel is crimp-capped, and the mixture is heated to 130C for 60 min in a single-mode microwave device. Then, the suspension is filtered, the filtrate is transferred to another microwave process vial, and tetrakis(triphenylphosphine)- palladium(O) (0.1 equivalents), 2 M aqueous sodium carbonate solution (4 equivalents) and the 5-bromopyrrolo [2, 1 -f] [ 1 ,2,4]triazine A (1 equivalent) are added. The vial is crimp-capped, and the mixture is heated to 140C for 1 h in a single-mode microwave device. The crude reaction mixture thus obtained is directly injected onto a preparative HPLC column for separation and purification of the target compound C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,162744-59-4, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Bayer Pharma Aktiengesellschaft; KLAR, Juergen; VOEHRINGER, Verena; TELSER, Joachim; LOBELL, Mario; SUessMEIER, Frank; LI, Volkhart Min-Jian; BOeTTGER, Michael; GOLZ, Stefan; LANG, Dieter; SCHLEMMER, Karl-Heinz; SCHLANGE, Thomas; SCHALL, Andreas; FU, Wenlang; WO2013/4551; (2013); A1;,
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Related Products of 3840-31-1 ,Some common heterocyclic compound, 3840-31-1, molecular formula is C10H14O4, 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.

General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, CuCl (0.05 mol, 5 mol%), DABCO (0.10 mol, 10 mol%), 4-HO-TEMPO (0.05 mmol, 5 mol%) were added. Substrates 1 (1 mmol) and NH3 (aq, 25-28%, 3 mmol, 3.0 equiv) in CH3CN (2 mL) were added subsequently. Then the reaction mixture was stirred at room temperature for 24 h in the presence of an air balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography to afford the corresponding products.

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. 3840-31-1, (3,4,5-Trimethoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hu, Yongke; Chen, Lei; Li, Bindong; Chinese Chemical Letters; vol. 29; 3; (2018); p. 464 – 466;,
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Related Products of 869725-53-1, 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 869725-53-1 as follows.

To a vial equipped with a stir bar were added 265 N-(4-fluorophenyl)-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)oxetane-3-carboxamide (I-155; see Ex. 76 for preparation) (500 mg, 1.26 mmol), 671 (2-bromo-5-(trifluoromethyl)phenyl)methanol (320 mg, 1.26 mmol), potassium phosphate tribasic (aq. solution 1M) (2511 mul, 2.51 mmol), (2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate, and 45 THF (1.26E+04 mul). The vial was purged with nitrogen, sealed, and heated to 40 C. for 1.5 h. After 1.5 h, the crude was washed with EtOAc and sat. NaHCO3. Combined organics were dried over MgSO4, filtered, and concentrated under reduced pressure. The material was dry loaded onto a 120 g column, and the column was run from 100% 6 DCM to 100% 10 EtOAc. The desired product was eluted and fractions were collected and concentrated under reduced pressure. The material was added to a vial, and 70 ACN was slowly added dropwise. Almost immediately, a solid crashed out and there was a resulting liquid. More ACN was added dropwise, swirled, and the solid did not go into solution. The mixture was heated with a heat gun to obtain a uniform solution. The mixture was undisturbed for 3.5 h. After 3.5 h, the sample was moved to the refrigerator for 12 h. After 12 h, the mixture was rinsed with cold (chilled with ice bath) ACN, and the 672 title compound was obtained as a solid. MS (ESI) calc’d for C23H18F4N2O3[M+H]+, 447; found, 447. 1H NMR (600 MHz, DMSO-d6) delta 10.14 (s, 1H), 8.75 (d, J=1.7 Hz, 1H), 8.01 (dd, J=8.2, 2.4 Hz, 1H), 7.97 (s, 1H), 7.78 (d, J=6.9 Hz, 1H), 7.75-7.70 (m, 2H), 7.63 (dd, J=60.7, 8.0 Hz, 2H), 7.25-7.17 (m, 2H), 5.51 (t, J=5.4 Hz, 1H), 5.15 (dd, J=76.2, 6.4 Hz, 4H), 4.52 (d, J=5.4 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,869725-53-1, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
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Synthetic Route of 722-92-9, 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. 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, 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.

2-(4-Ethylamino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol To a solution of 3.0 gm of 2-(4-Amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (Matrix Scientific, Columbia, S.C.) in 30 ml of methylene chloride was added 2.4 ml of triethyl amine, 1.2 ml of acetic anhydride, and 100 mg of dimethylaminopyridine. The mixture was allowed to stir at room temperature for 16 hrs. An additional 2.4 ml of triethyl amine and 1.2 ml of acetic anhydride was added and the mixture was stirred for an additional 6 hrs. The solution was evaporated and purified by column chromatography (1:1 Ethyl Acetate:Hexane) to give 3.1 gm of material that was used in the next step. To this material dissolved in 30 ml of tetrahydrofuran cooled to 0 degrees C. was added 1.6 gm of lithium aluminum hydride. This solution was stirred for 16 hrs and quenched with 1 N sodium hydroxide. This was then extracted with ethyl acetate and dried over anhydrous sodium sulfate. Chromatography gave 2.188 gm of the named product. 1H NMR was consistent with the structure.

According to the analysis of related databases, 722-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Orphagen Pharmaceuticals; Thacher, Scott; Li, Xiaolin; Babine, Robert; Tse, Bruno; US8389739; (2013); B1;,
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Reference of 5339-85-5, 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. 5339-85-5, name is 2-(2-Aminophenyl)ethanol. A new synthetic method of this compound is introduced below.

General procedure: A test tube (25 mL) wascharged with 2-aminophenethyl alcohol 1? (0.5 mmol, 1 equiv), aldehyde 2?? (0.75mmol, 1.5 equiv), AgOTf (0.025 mmol, 5 mol%), HOTf (0.05 mmol, 10 mol%), and toluene (3 mL) were added. Themixture was stirred at 120 oC in air for 12 hours, thereaction was cooled down to room temperature, the mixture was quenched by sat.aq. NaHCO3, and diluted with 10 mL dichloromethane and washed with10 mL H2O. The aqueous layer was extracted twice withdichloromethane (10 mL) and the combined organic phase was dried over Na2SO4.After evaporation of the solvents, the residue was purified by silica gelchromatography (hexane/AcOEt = 30:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5339-85-5, 2-(2-Aminophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Article; Xu, Xuefeng; Zhang, Xu; Liu, Wenming; Zhao, Qiang; Wang, Zhiqiang; Yu, Lintao; Shi, Fu; Tetrahedron Letters; vol. 56; 24; (2015); p. 3790 – 3792;,
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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 27871-49-4, name is (S)-Methyl 2-hydroxypropanoate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C4H8O3

Under an Ar atmosphere, to a solution of methyl L-lactate (10.0 g, 96.1 mmol) in THF (100.0 mL) were added NEt3 (33.5 mL 240.2 mmol), DMAP (1.17 g, 9.6 mmol) and TBSCl (19.3 g, 128.1 mmol) at 0C, and the mixture was stirred for 24 h at r.t. The reaction mixture was diluted with Et2O, successively washed with 10% HCl aq. and sat. NaHCO3 aq., dried over MgSO4, filtered, and concentrated in vacuo. The resulting oil was purified by column chromatography on silica gel (hexane:AcOEt = 5:1) to afford the TBS ether (S-1) (20.9 g, 95.5 mmol, 99%) as a colorless oil.

With the rapid development of chemical substances, we look forward to future research findings about 27871-49-4.

Reference:
Article; Sugimoto, Kenji; Kobayashi, Yuta; Hori, Ayana; Kondo, Takashi; Toyooka, Naoki; Nemoto, Hideo; Matsuya, Yuji; Tetrahedron; vol. 67; 40; (2011); p. 7681 – 7685;,
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