Author: tianli

Synthetic Route of 57641-66-4 , The common heterocyclic compound, 57641-66-4, name is 2-(2-Bromoethoxy)ethanol, molecular formula is C4H9BrO2, 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 solution of 2-(2-bromoethoxy)ethanol (2.4 g) and teri-butyldimethylchlorosilane (2.4 g) in NN-dimethyl formamide (14.3 mL) was added NN-diisopropylethylamine (6.2 mL), and the reaction was allowed to stir for 6 hours. The reaction was diluted with ethyl acetate, water and brine. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with water then brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase MPLC on a Teledyne Isco CombiFlash Rf+ 80 g gold silica gel column eluting with 0-15% ethyl acetate in heptanes to give the title compound. NMR (500 MHz, CDC13) delta ppm 3.84-3.80 (m, 2H), 3.79-3.75 (m, 2H), 3.60-3.56 (m, 2H), 3.48-3.43 (m, 2H), 0.90 (s, 9H), 0.07 (s, 6H).

The synthetic route of 57641-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; BRAJE, Wilfried; DOHERTY, George; JANTOS, Katja; JI, Cheng; JUDD, Andrew; KUNZER, Aaron; MASTRACCHIO, Anthony; SONG, Xiaohong; SOUERS, Andrew; SULLIVAN, Gerard; TAO, Zhi-Fu; LAI, Chunqui; KLING, Andreas; POHLKI, Frauke; TESKE, Jessc; WENDT, Michael; BRADY, Patrick; WANG, Xilu; PENNING, Thomas; MICHAELIDES, Michael; (448 pag.)WO2019/35927; (2019); A1;,
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Reference of 2077-19-2 , The common heterocyclic compound, 2077-19-2, name is 2-(4-Bromophenyl)propan-2-ol, molecular formula is C9H11BrO, 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.

[0001247] A mixture of 2-(4-bromophenyl)propan-2-ol (34 mg, 0.15 mmol), Compound 356A (75 mg, 0.15 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) (7 mg, 8.2 muiotaetaomicron), sodium carbonate (44 mg, 0.30 mmol), water (0.5 mL), and 1,4-dioxane (5 mL) was stirred under nitrogen atmosphere at 80 C for 2 h. After cooling, the reaction mixture was treated with water (5 mL), extracted with ethyl acetate (10 mL x 3), washed with brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with prep-HPLC. The solution was adjusted to pH = 8.0 with sodium bicarbonate solution, extracted with ethyl acetate (50 mL x 2), dried over anhydrous sodium sulfate, filtered, and concentrated to furnish Compound 356. LC-MS (ESI) m/z: 563 [M+H]+; 1H-NMR (CDCI3, 400 MHz): delta (ppm) 1.42-1.75 (m, 6H), 1.79-1.86 (m, 4H), 2.74-2.81 (m, 4H), 2.96-3.04 (m, 2H), 4.24-4.31 (m, 6H), 5.05 (d, J= 2.4 Hz, 1H), 6.70-6.76 (m, 2H), 7.39 (d, J= 8.8 Hz, 1H), 7.75-7.64 (m, 5H), 7.68 (d, J= 9.2 Hz, 2H), 8.31 (d, J= 8.8 Hz, 2H).

The synthetic route of 2077-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
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Electric Literature of 454-91-1, 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 454-91-1, name is 1-[3-(Trifluoromethyl)phenyl]ethanol. This compound has unique chemical properties. The synthetic route is as follows.

4-(2-Fluorophenyl)-2-methyl-2H-pyrazol-3-amine (150 mg, 0.78 mmol) and triphosgene (303 mg, 1.02 mmol) were dissolved in dichloromethane (3 mL). Toluene (8 mL) was added and the mixture was sealed. The mixture was stirred in an ice bath and TEA (0.9 mL, 8.0 eq) was added. The mixture was stirred at 85 C for 20 minutes and l-(3-(trifluoromethyl)-phenyl)ethanol (194 mg, 1.02 mmol) in toluene (2 mL) was added. The mixture was stirred at 90 C for 2 fir. Solvents were evaporated and the residue was extracted with ethyl acetate and water. The organic layer was washed with brine and dried. Solvents were evaporated and the residue was purified by ISCO flash column chromatography (0% to 60% ethyl acetate in hexanes) to give [4-(2-fluoro- phenyl)-2-methyl-2H-pyrazol-3-yl]-carbamic acid l-(3-trifluoromethyl-phenyl)-ethyl ester as a pale yellow waxy material (226 mg, 70.7% yield). 1H-NMR (400 MHz, DMSO-de) delta ppm 1.11- 1.29 (m, 0.6H), 1.55 (br d, J=5.81 Hz, 2.4H), 3.65 (s, 3H), 5.73-5.85 (m, 1H), 7.06-7.24 (m, 2H), 7.25-7.52 (m, 3H), 7.56-7.82 (m, 4H), 9.29 (br s, 0.2H), 9.66 (s, 0.8H); LC/MS calcd for C2oHi7F4N302 (m/e) 407.0, obsd 408.0 (M+H, ES+)..

According to the analysis of related databases, 454-91-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GABRIEL, Stephen Deems; HAMILTON, Matthew Michael; QIAN, Yimin; SIDDURI, Achyutharao; WO2013/189862; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 928-51-8, 4-Chlorobutan-1-ol, 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, 928-51-8, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

To the reaction vessel, 5.00 g of 4-chlorobutanol,0.58 g of pyridinium p-toluenesulfonate,50 mL of dichloromethane was added.4.65 g of 3,4-dihydro-2H-pyran was added dropwise while cooling with ice.After stirring, it was washed with sodium bicarbonate water and brine.Purification by column chromatography gave 7.99 g of a compound represented by the formula (I-7-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,928-51-8, its application will become more common.

Reference:
Patent; DIC CORPORATION; HORIGUCHI, MASAHIRO; KUSUMOTO, TETSUO; (71 pag.)JP2015/205843; (2015); A;,
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Related Products of 62058-03-1 ,Some common heterocyclic compound, 62058-03-1, molecular formula is C10H17NO, 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 solution of Compound 29(102mg) in methylene chloride(2ml) were added hydroxy adamantanamine(81mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(82mg), 1-hydroxybenzotriazole(14mg) and triethylamine(115mul), then the resulting solution was stirred at room temperature for 13hrs. After termination of the reaction, the solution was acidified with 2N HCl aqueous soln. and extracted with methylene chloride. The organic layer was washed with sat. sodium hydrogencarbonate soln. and brine successively, and dried with sodium sulfate. The residue was purified by silicagel columnchromatography to afford Compound C-202(123mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62058-03-1, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; EP1953145; (2008); A1;,
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Related Products of 3973-18-0, 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. 3973-18-0, name is Propynol ethoxylate, molecular formula is C5H8O2, 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: To a 0.30mL of a solution of azide 14 (23mM in tBuOH-H2O (2: 1)) in an eppendorf, 0.10mL of a solution of the corresponding alkyne (a-s) (83mM in tBuOH) was added followed by 25muL of an aqueous solution of sodium ascorbate (30mM) and 25muL of an aqueous solution of CuSO4 (9.4mM). The final concentration of the azide 14 in each eppendorf was 15mM. The resulting mixtures were shaken at room temperature for 24h and monitored for completion by TLC and ESI-MS (see Supplementary data for mass spectra analysis). Then, the reactions were diluted with water to the desired concentration and placed in a 96-well microtiter plate in order to perform the enzymatic assays. In the preliminary screening of the resulting crude (pyrrolidin-2-yl)triazoles 14a-s, % of inhibition towards beta-glucosidase from almonds was determined at 10muM of the pyrrolidine-triazole on each well (assuming quantitative conversion in the click reaction).

According to the analysis of related databases, 3973-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Martinez-Bailen, Macarena; Carmona, Ana T.; Moreno-Clavijo, Elena; Robina, Inmaculada; Ide, Daisuke; Kato, Atsushi; Moreno-Vargas, Antonio J.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 532 – 542;,
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Related Products of 349-75-7, 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. 349-75-7, name is (3-(Trifluoromethyl)phenyl)methanol. A new synthetic method of this compound is introduced below.

General procedure: To a solutionof a carboxylic acid in dry DMF (0.2±1.6 mL), CDI (2±2.2 equiv) was added and the mixturewas stirred at rt for 1 h under argon atmosphere. An alcohol (1.1±2 equiv), DBU (0.5±2 equiv)and DMAP (0.1 equiv) were subsequently added and the reaction mixture was microwave irradiatedat 50 C for 1 h. The reaction was quenched with ice water and extracted with EtOAc.The combined organic layers were washed with a saturated solution of NaHCO3 in water,brine and the solvent was evaporated under reduced pressure at 40 C. The crude residue waspurified by flash column chromatography with appropriate eluents and a gradient.3-(trifluoromethyl)benzyl 2-[(4-methoxyphenoxy)methyl]-5-methyl-6-[[3-(trifluoromethyl)benzyl]oxy]pyrimidine-4-carboxylate (21). General procedure IV was followed.Compound 16 (0.060 g, 0.13 mmol), dry DMF (0.2 mL), CDI (43 mg, 0.27 mmol, 2 equiv), 3-(trifluoromethyl)benzyl alcohol (36 muL, 0.27 mmol, 2 equiv), DBU (0.010 mL, 0.067 mmol, 0.5equiv), DMAP (1.6 mg, 0.013 mmol, 0.1 equiv). Flash chromatography eluents: cyclohexane(A), EtOAc (B); gradient: 6%45% B×10 CV. Compound 21 was isolated as a yellow oil (49mg, 0.081 mmol, 62% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,349-75-7, (3-(Trifluoromethyl)phenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Provenzani, Riccardo; Tarvainen, Ilari; Brandoli, Giulia; Lempinen, Antti; Artes, Sanna; Turku, Ainoleena; Jaentti, Maria Helena; Talman, Virpi; Yli-Kauhaluoma, Jari; Tuominen, Raimo K.; Boije af Gennaes, Gustav; PLoS ONE; vol. 13; 4; (2018);,
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Adding a certain compound to certain chemical reactions, such as: 186020-66-6, tert-Butyl 12-Hydroxy-4,7,10-trioxadodecanoate, 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, 186020-66-6, blongs to alcohols-buliding-blocks compound. Quality Control of tert-Butyl 12-Hydroxy-4,7,10-trioxadodecanoate

Second Step tert-Butyl 3-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]propanoate tert-Butyl 3-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]propanoate (488 mg, 1.75 mmol) and triethylamine (532 mg, 5.26 mmol) were dissolved in dichloromethane (15 mL), and tosyl chloride (435 mg, 2.28 mmol) was added. After the mixture was stirred at room temperature for 17 hours, the reaction mixture was concentrated, and the resultant residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to obtain the title compound (550 mg, 73%) as colorless clear oil. LCMS: m/z 450[M+H2O]+ HPLC retention time: 0.90 minutes (analysis condition SQD-FA05)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,186020-66-6, its application will become more common.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; OHTAKE, Yoshihito; OKAMOTO, Naoki; ONO, Yoshiyuki; KASHIWAGI, Hirotaka; KIMBARA, Atsushi; HARADA, Takeo; HORI, Nobuyuki; MURATA, Yoshihisa; TACHIBANA, Kazutaka; TANAKA, Shota; NOMURA, Kenichi; IDE, Mitsuaki; MIZUGUCHI, Eisaku; ICHIDA, Yasuhiro; OHTOMO, Shuichi; HORIBA, Naoshi; (310 pag.)US2016/2251; (2016); A1;,
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Synthetic Route of 7073-69-0, 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. 7073-69-0, name is 2-(2-Bromophenyl)propan-2-ol. A new synthetic method of this compound is introduced below.

General procedure: Using diaryl acetylenesA 5-mL two-necked flask equipped with a stir bar was charged with [RhCl(cod)]2 (0.0125 mmol,6.16 mg), BINAP (0.0125 mmol, 7.78 mg), 1a-c (0.25 mmol), KI (0.25 mmol, 41.5 mg), and Na2CO3(1.0 mmol, 106.0 mg). The central neck of the flask was equipped with a reflux condenser havinga N2 gas-bag (2 L), which was connected by a three-way stopcock at its top, and a rubber septumwas inserted i n to the side neck. The flask was evacuated and backfilled with N2 (three times).Xylene (1.0 mL), 2a (0.75 mmol, 161.3 mg), and furfural (1.75 mmol, 168.2 mg), were then added.After degassing the reaction mixture three times by the freeze-pump-thaw method, the flask wasfilled with N2. The mixture was placed in an oil bath that had been preheated to 140 C for 20 h.After cooling to room temperature, the resulting solution was filtered through a pad of celite, andthe filtrate was concentrated in vacuo. The resulting crude product was purified by flash columnchromatography on silica-gel to afford 3aa-3ac.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7073-69-0, 2-(2-Bromophenyl)propan-2-ol, and friends who are interested can also refer to it.

Reference:
Article; Furusawa, Takuma; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Morimoto, Tsumoru; Kakiuchi, Kiyomi; Chemistry Letters; vol. 46; 7; (2017); p. 926 – 929;,
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Application of 229027-89-8, Adding some certain compound to certain chemical reactions, such as: 229027-89-8, name is 2-Bromo-4-fluorobenzyl Alcohol,molecular formula is C7H6BrFO, 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 229027-89-8.

A mixture of (2-bromo-4-fluorophenyl)methanol (250g, 1.22 mol) and 3,4-dihydro-2H-pyran (205 g, 2.44 mol) is dissolved in DCM (2000 mL). To this solution is added pyridinium p-toluenesulfonate (15g, 0.06 mol). The resulting solution is stirred overnight at rt and then treated with saturated NaHC03. After extraction with EtOAc, the organic layer is washed with water and brine, dried, concentrated and purified by column chromatography over silica gel to provide the product of this step (281 g, yield 80%) as colorless oil.

According to the analysis of related databases, 229027-89-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; ANACOR PHARMACEUTICALS INC.; AKAMA, Tsutomu; JARNAGIN, Kurt; PLATTNER, Jacob J.; PULLEY, Shon Roland; WHITE, William Hunter; ZHANG, Yong-Kang; ZHOU, Yasheen; WO2014/149793; (2014); A1;,
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