Tag: M.W=200-300

Electric Literature of 1261524-75-7, 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.1261524-75-7, name is 3-Bromo-2-chlorobenzyl Alcohol, molecular formula is C7H6BrClO, molecular weight is 221.48, as common compound, the synthetic route is as follows.

To a solution of (3-bromo-2-chlorophenyl)methanol(4.57 g, 20.63 mmol, 1 equiv.) in DCM(200 mL) were added DMF(45.2 mg, 0.62 mmol, 0.03 equiv.) and SOCl2(61.4 g, 516.10 mmol, 25.01 equiv.) dropwise at 0 degrees C under nitrogen atmosphere. The resulting mixture was stirred for 2 days at ambient temperature. The desired product could be detected by LCMS. The mixture was concentrated to get crude product. The crude product was added water(400mL) and extracted with EA (400mLx2). The organic layers was washed with saturated brine (200ml), dried over anhydrous Na2SO4, filtered and concentrated to give desired product. The residue was purified by silica gel column chromatography, eluted with EtOAc / PE (1:50 to 1:40) to afford 1-bromo-2-chloro-3-(chloromethyl)benzene (4.9 g, 98.98%) as a yellow liquid.

The chemical industry reduces the impact on the environment during synthesis 1261524-75-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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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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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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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 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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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 2425-41-4, name is (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol

(8) A mixture of 2-phenyl-5,5-dihydroxymethyl-1,3-dioxane (2.2 g, 0.01 mol)4-nitrophthalonitrile (1.73 g, O. Olmol),Potassium carbonate (6.9 g, 0.05 mol)Add N, N-dimethylformamide, 50 mL; (9) The reaction was heated at 80 C for 12 hours;(10) After the reaction was stopped, the potassium carbonate was filtered off, the solvent was removed,Column chromatography using methanol / dichloromethane = 1/200 phase gave a white solid which was recrystallized from n-hexane / methylene chloride in a yield of 42%

With the rapid development of chemical substances, we look forward to future research findings about 2425-41-4.

Reference:
Patent; Shandong University , Weihai; BAI, MING; LU, RAN; WAN, PEIHONG; (8 pag.)CN104557949; (2016); B;,
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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. 78573-45-2, name is 3-(3-(Trifluoromethyl)phenyl)propan-1-ol, molecular formula is C10H11F3O, 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. Quality Control of 3-(3-(Trifluoromethyl)phenyl)propan-1-ol

2.51 g (14.7 mmol) of (R)-1-(1-naphthyl)-ethylamine and 3.01 g (14.7 mmol) of 3-[3-(trifluoromethyl)phenyljpropanol are weight into a flask. The mixture is diluted with 6 ml of toluene and 53 mg (0.45 mol percent) of {IrCp*Cl2]2 is added. The mixture is heated in a bath at t=110 °C under a reflux condenser in the nitrogen atmosphere for 20 hours. After cooling down, the reaction mixture is diluted with a mixture of hexane and ethyl acetate. On addition of a solution of hydrogen chloride in diethylether, a solid salt is formed and by sucking it off 4.83 g (83 percent) of Cinacalcet hydrochloride is obtained in a purity of 97.8 percent (HPLC). The method described in Example 1 was used for HPLC determination.

With the rapid development of chemical substances, we look forward to future research findings about 78573-45-2.

Reference:
Patent; ZENTIVA, K.S.; VLASAKOVA Ruzena; HAJICEK Josef; WO2013/75679; (2013); A1;,
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Related Products of 83647-43-2, 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. 83647-43-2, name is (3-Bromo-2-methylphenyl)methanol, molecular formula is C8H9BrO, 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.

To a flask charged with (3-bromo-2- methylphenyl)methanol (6.0 g, 30 mmol) was added a 1M TFA solution of thallium trifluoroacetate (16.2 g, 29.8 mmol). The mixture was stirred at RT overnight. Analysis by TLC showed no starting material remaining. The solvent was removed under vacuum, and the residue was pumped under high vacuum for 30 min to ensure complete removal of TFA. To the residue was then added palladium(II) chloride (529 mg, 2.98 mmol), lithium chloride (2.53 g, 59.7 mmol), magnesium oxide (2.41 g, 59.7 mmol), and MeOH (150 mL). The reaction was flushed with CO twice, and kept under CO at room temperature. Analysis by LC showed a big product spot within 2 hours. To this solution was added ethyl acetate to precipitate the salts. The black solution was filtered through a CELITE pad, washed with EtOAc, adsorbed onto silica and purified by silica gel chromatography to afford title compound. 1H-NMR (500 MHz, CDCI3) delta ppm 7.71 (d, J = 8.0 Hz, 1H), 7.58 (d, J = 8.0 Hz, 1H), 5.25 (s, 2H), 2.37 (s, 3H).

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 83647-43-2, (3-Bromo-2-methylphenyl)methanol.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DING, Fa-Xiang; DONG, Shuzhi; FRIE, Jessica; GU, Xin; JIANG, Jinlong; PASTERNAK, Alexander; TANG, Haifeng; WU, Zhicai; YU, Yang; SUZUKI, Takao; WO2014/18764; (2014); A1;,
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Application of 162744-59-4, 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 162744-59-4 as follows.

A solution of 5-Bromo-2-hydroxymethyl-1, 3-difluoro-benzene (0. 89g, 4.0 mmol) and 30 wt% of hydrogen bromide in acetic acid was stirred at room temperature for 90 minutes before it was poured into 80 ml of water. The mixture was extracted with pentane (3 X 50 ML) and the combined organic layers were washed with water (3 X 20 ML), dried over MGSO4 and concentrated at low pressure to afford the desired product (10.0 g, 98% YIELD). 1H NMR (CDC13) 8 : 4.47 (s, 2H), 7.09-7. 10 (m, 1H), 7. 12-7. 13 (m, 1H).

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; PFIZER INC.; WO2004/74270; (2004); A2;,
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Synthetic Route of 3344-77-2, 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.3344-77-2, name is 12-Bromododecan-1-ol, molecular formula is C12H25BrO, molecular weight is 265.23, as common compound, the synthetic route is as follows.

Example 2 Preparation of (12-bromododecyloxy)(tert-butyl)dimethylsilane (4) Tert-butyldimethylsilyl chloride (5.61 g; 37.3 mmol; 1.5 eq.) and imidazole (2.54 g; 37.3 mmol; 1.5 eq.) are added to a solution of 12-bromododecan-1-ol (6.6 g; 24.9 mmol; 1 eq.) in dichloromethane (60 ml) at room temperature. After 4 h, the reaction mixture is poured into a saturated solution of NH4Cl (100 ml) and then extracted with ether (3*100 ml). The organic phase is washed with a saturated solution of NaCl, dried on MgSO4, filtered then evaporated. The crude reaction product is purified by silica gel chromatography (eluent: hexane-AcOEt: 95-5) to yield 9.17 g of a colorless oil. Yield: 99percent Empirical formula: C18H39BrOSi

Statistics shows that 3344-77-2 is playing an increasingly important role. we look forward to future research findings about 12-Bromododecan-1-ol.

Reference:
Patent; Centre National de la Recherche Scientifique(CNRS); Universite de Luxembourg; US2010/48731; (2010); A1;,
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