Author: Jessica.F

Application of 2672-58-4, 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 2672-58-4 as follows.

Will be bothTrimethyl trimellitateSoluble in methanol, trimethyl t-trimellitate and methanol to the mass ratio of 1:25,The molar ratio of trimethyl terephthalate to KOH was 1: 2,0 stirring 2h,Natural warming to 25 ,(4 × 10ml), dried over MgSO4, and the chloroform was removed by filtration to give 3,5-dichlorophenol, which was washed with water and concentrated in water. Dibutyric acid-1-benzoate..

According to the analysis of related databases, 2672-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CNOOC Tianjin Chemical Research and Design Institute Co., Ltd.; CNOOC Energy Development Co., Ltd.; Li, Zhiyuan; Wang, Sufang; Xu, Hui; Ding, Qiuwei; Ding, Shu; Lin, Bei; Yu, Xiaowei; Teng, Houkai; (8 pag.)CN106543083; (2017); A;,
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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. 432022-88-3, name is Methyl 4-bromo-3,5-dimethylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 432022-88-3

II?TERMEDIATE 49 Methyl 4- 5- 14-( (4S,5R)-5 – 13 -fluoro-5-(trifluoromethyl)phenyl] -4-methyl-2-oxo- 1,3 – oxazolidin-3-yBmethyl-2-(methylsulfanylnyrimidin-5-yl1-6-methoxynyridin-3-yB -3.5- dimethylbenzoateA mixture of (4S,5R)-3 – { [5-(5-chloro-2-methoxypyridin-3 -yl)-2-(methylsulfanyl)pyrimidin-4- yl]methyl} -5- [3 -fluoro-5-(trifluoromethyl)phenyl] -4-methyl- 1,3 -oxazolidin-2-one(INTERMEDIATE 18, 211 mg, 0.389 mmol), bis(pinacolato)diboron (296 mg, 1.17 mmol), and potassium acetate (114 mg, 1.17 mmol) in N,N-dimethylacetamide (2.0 mL) was degassed three times with nitrogen gas before the addition of(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl) [2-(2-aminoethyl)phenyl)]palladium(II) chloride (XPHOS Biphenyl Precatalyst) (15.5 mg, 0.0 19 mmol). The system was degassed three times and was then heated to 130 C for24 hours. LC/MS analysis indicated complete conversion to the product, but almost exclusively as the boronic acid. For this reason the crude reaction mixture was taken directly into the next step. Accordingly, methyl 4-bromo-3 ,5-dimethylbenzoate (142 mg, 0.584 mmol), (1,1 bis(di tert-butylphosphino)ferrocene palladium dichloride (24.5 mg, 0.039 mmol), and aqueous potassium carbonate (0.389 mL, 2.0 M) were added. The mixture was degassed, flushed withnitrogen and heated to 100C for 45 minutes. The reaction was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography to afford methyl 4-{5-[4-({(4S,5R)-5-[3-fluoro- 5-(trifluoromethyl)phenyl] -4-methyl-2-oxo- 1,3 -oxazolidin-3-yl} methyl)-2- (methylsulfanyl)pyrimidin-5-yl] -6-methoxypyridin-3 -yl} -3 ,5-dimethylbenzoate (158 mg, 0.236mmol). LCMS (M+H)*: 671.1

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACTON, John, J., III; YE, Feng; VACHAL, Petr; SHA, Deyou; DROPINSKI, James, F.; CHU, Lin; ONDEYKA, Debra; KIM, Alexander, J.; COLANDREA, Vincent, J.; ZANG, Yi; ZHANG, Fengqi; DONG, Guizhen; WO2013/165854; (2013); A1;,
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Application of 33491-30-4, These common heterocyclic compound, 33491-30-4, name is 8-Bromo-2H-chromen-2-one, 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: General synthetic procedure for 3a/3b/3c: 6-Bromocoumarin(0.5 g, 2.23 mmol), (4-ethynyl)benzaldehyde (0.29 g, 2.23 mmol)were dissolved in THF-triethylamine (1:1, v/v, 120 mL) and themixture was deaerated for 10 min with nitrogen bubbling and thenPd(PPh3)2Cl2 (31 mg, 2mol%), PPh3 (23 mg, 4 mol%)and CuI (8 mg,2mol%) were added. The solution was deaerated for an additional5 min; after that, reaction was left under nitrogen at 60C for 12 h.After completion of the reaction, the reaction mixture was cooledat room temperature and the solvent was evaporated. The crudeproduct was dissolved in CH2Cl2 and purified by a columnchromatography on a silica gel using (chloroform) as an eluent.

Statistics shows that 8-Bromo-2H-chromen-2-one is playing an increasingly important role. we look forward to future research findings about 33491-30-4.

Reference:
Article; Reddy, T. Sheshashena; Choi, Myung-Seok; Journal of Photochemistry and Photobiology A: Chemistry; vol. 351; (2018); p. 108 – 114;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 146307-51-9, name is trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a solution of (frans)-methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate (Intermediate 18A) (1 .5 g, 5.8 mmol) in EtOH (24 mL) and THF (2.7 mL), cooled on ice, was added calcium chloride (1 .29 g, 1 1 .7 mmol) portion wise to give a milky suspension. NaBH4 (882 mg, 23.3 mmol) was then added portion wise over ca. 25 min and the reaction was stirred on ice for 1 h. The bath was removed and the mixture was allowed to stir at room temperature overnight. The reaction was cooled to 10 C and to this was added 5% aqueous K2CO3 (5.4 mL) dropwise, to give a pH of ca. 1 1 . A white precipitate formed and was isolated by filtration. The solid was stirred with EtOAc (50 mL) and water (14 mL). The layers were separated and the organic layer was washed with 0.5 M aqueous HCI (5 mL), water and brine, dried over MgS04, filtered, and concentrated to give the title compound (474 mg) as a white solid. The initial filtrate was concentrated, then dilute with saturated aqueous NH4CI and extracted with EtOAc (3X). Combined organics were washed with brine and dried over Na2SC>4, filtered, and concentrated to give the title compound (724 mg) as a white solid. Total isolated product was 1 .1 9 g (89% yield). 1H NMR (400 MHz, CD3SOCD3) delta 0.78-0.93 (m, 2 H), 1 .01 -1 .15 (m, 2 H), 1 .35 (s, 9 H), 1 .64-1 .80 (m, 4 H), 3.10 (d, J = 8 Hz, 1 H), 3.16 (t, J = 6 Hz, 2 H), 4.33 (t, J = 5 Hz, 1 H), 6.64 (d, J = 8 Hz, 1 H).

According to the analysis of related databases, 146307-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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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. 2459-25-8, name is Methyl 2-naphthoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-naphthoate

General procedure: The appropriate aryl-ester 18a-e (1 eq), was added of EtOH (2.22 ml*mmol/eq) followed by hydrazine monohydrate (3 eq). The solution was refluxed overnight, then cooled to room temperature. The precipitate obtained was filtered and washed with cold EtOH and n-hexane to give the pure product.

The synthetic route of 2459-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella; European Journal of Medicinal Chemistry; vol. 149; (2018); p. 56 – 68;,
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Electric Literature of 167760-75-0, These common heterocyclic compound, 167760-75-0, name is Methyl 4-amino-3-(trifluoromethyl)benzoate, 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.

6.54 g (30 mmol) methyl 4-amino-3-trifluoromethyl-benzoate are suspended in 50 ml 32% hydrochloric acid and cooled to -20 C. A solution of 2.28 g (33 mmol) sodium nitrite in 20 ml of water is added dropwise. The mixture is stirred for 3 hours at -20 to -10 C., then 27.08 g (120 mmol) tin-(II)-chloride dihydrate in 30 ml hydrochloric acid are added dropwise within 0.25 hours. The reaction mixture is stirred for 2 hours at -10 C., then acidified with cooling. The suspension is suction filtered through kieselguhr and washed with chloroform. The phases of the filtrate are separated, the aqueous phase is extracted with chloroform. The combined organic phases are dried and evaporated to dryness. The residue is precipitated as the hydrochloride, then stirred with diethyl ether. Yield: 4.02 g (50% of theoretical)

Statistics shows that Methyl 4-amino-3-(trifluoromethyl)benzoate is playing an increasingly important role. we look forward to future research findings about 167760-75-0.

Reference:
Patent; Breitfelder, Steffen; Maier, Udo; Hoenke, Christoph; Joergensen, Anne T.; Pautsch, Alexander; Brandl, Trixi; Grauert, Matthias; Hoffmann, Matthias; Scheuerer, Stefan; Erb, Klaus; Pieper, Michael; Pragst, Ingo; US2007/238730; (2007); A1;,
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These common heterocyclic compound, 61500-87-6, name is Methyl 2-amino-4-(trifluoromethyl)benzoate, 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. Safety of Methyl 2-amino-4-(trifluoromethyl)benzoate

Step 2: methyl 2-(acetylamino)-4-(trifluoromethyl)benzoate To a solution of the product from Step 1 (5.34 g) in dioxane (25 ml) was added acetic anhydride (6 ml) and pyridine (4 ml). After 60 hours of stirring at 80C, the solution was concentrated under reduced pressure and the residue was dissolved into ethyl acetate. The organic layer was washed with 2M sodium carbonate, 10% aqueous HCl, water and brine, dried over sodium sulfate and evaporated. The product was purified by flash chromatography (ISCO, 5%-20% ethyl acetate in hexanes) to provide a beige solid (5.27 g). LRMS (ES+) m/z 262.0 (M+H)+.

The synthetic route of Methyl 2-amino-4-(trifluoromethyl)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.R.L.; RUDD, Michael, T.; MCCAULEY, John; LIVERTON, Nigel; GRISE-BARD, Christiane; BROUCHU, Marie-Christine; CHARRON, Sylvie; AULAKH, Virender; BACHAND, Benoit; BEAULIEU, Patrick; ZAGHDANE, Helmi; HAN, Yongxin; FERRARA, Marco; HARPER, Steven; SUMMA, Vincenzo; CHACKALAMANNIL, Samuel; VENKATRAMAN, Srikanth; SHAH, Unmesh; VELAZQUEZ, Francisco; WO2013/74386; (2013); A2;,
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Reference of 2967-93-3, 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. 2967-93-3 name is Methyl 2-fluoro-5-methylbenzoate, This 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.

(Table B1, B36, Scheme B2-B3) N-(3,4-dichlorobenzyl)-5-(((4,5-dihydro-1H-imidazol-2-yl)amino)methyl)-2-fluorobenzamide Bromination step: A solution of methyl 2-fluoro-5-methylbenzoate (2.10 g, 12.49 mmol) (CAS No.2967-93-3 Combi Blocks) in CCl4 (60 mL) was allowed to reflux through a Dean Stark trap to remove trace amounts of water. The solution was cooled to ambient temperature and treated with N-bromosuccinimide (NBS) (2.44 g, 13.74 mmol) and 2,2’azobis(2-methylpropionitrile (AIBN) (0.20 g, 1.20 mmol). The solution was heated to reflux for an 18 hour period. The mixture was cooled to ambient temperature, filtered and the resulting filtrate was concentrated under reduced pressure. The crude was then purified on silica gel using EtOAc/hexanes as mobile phase. The desired fractions where concentrated under reduced pressure to afford methyl 5-(bromomethyl)-2-fluorobenzoate compound 1.9 g (61%): 1H NMR (400 MHz, CDCl3) delta 8.0 (m, 1H), 7.6 (m, 1H), 7.1 (m, 1H), 4.5 (s, 2H), 4.0 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-fluoro-5-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Vanderbilt University; Gogliotti, Rocco D.; Stauffer, Shaun R.; Jeon, KyuOk; Salovich, James M.; Macdonald, Jonathan D.; Mills, Jonathan J.; Meyers, Kenneth M.; Alvarado, Joseph R.; Han, Changho; Fesik, Stephen W.; Lee, Taekyu; (177 pag.)US2020/55824; (2020); A1;,
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Application of 697762-67-7,Some common heterocyclic compound, 697762-67-7, name is Methyl 5-bromo-2-chloro-3-methoxybenzoate, molecular formula is C9H8BrClO3, 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.

The compound (74.80 g, 0.27 mol) obtained in Step 4 was dissolved in dichloromethane (300 ml) and 1M boran tribromide/dichloromethane solution (700 ml, 0.70 mol) was added dropwise at 10C or below. After completion of the addition, the mixture was stirred at room temperature for 1.5 hrs. The reaction mixture was added to ice water (1500 ml) and the precipitated solid was collected by filtration. The filtrate was partitioned, and the aqueous layer was extracted with ethyl acetate (200 ml). The organic layers were combined and concentrated under reduced pressure. The solid collected by filtration and the residue were dissolved in diethyl ether (1000 ml) and 1N aqueous sodium hydroxide solution (1000 ml) was added for extraction. 2N Hydrochloric acid (500 ml) was added to the aqueous layer. The mixture was stirred and extracted with ethyl acetate (800 ml). The mixture was partitioned and the organic layer was washed successively with water and saturated brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give an object product (63.83 g, yield 95%) as a beige solid.1H NMR(DMSO-d6 300MHz) (delta) ppm: 7.23 (1H, d, J=2.4Hz), 7.28 (1H, d, J=2.4Hz), 10.99(1H, s), 13.55 (1H, brs)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-bromo-2-chloro-3-methoxybenzoate, its application will become more common.

Reference:
Patent; Japan Tobacco Inc.; EP1564210; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H14O2

To a cooled solution (-40 C) of DIPEA (4.1 mL, 29.57 mmol, 2.1 eq) in THF (25 mL), was added w-BuLi (2.5M in hexanes, 1 1.2 mL, 28.36 mmol, 2 eq.) drop wise and the mixture was then stirred for 0.5 hr and then cooled to -78 C. Next, a solution of tert-butyl cyclopropanecarboxylate (2 g, 14.08 mmol, 1 eq.) in THF (5 mL) was added and the reaction mixture was stirred for 4 h at -78 C. 1-Propene, 3-bromo- (3.6 mL 42.25 mmol, 3 eq.) was added and reaction mixture was stirred for 2 h at -78 C. The reaction was then quenched with NH4Cl (30 mL) and extracted with DCM. The organic layer was dried over Na2S04 and concentrated to give tert-butyl 1-allylcyclopropane-l -carboxylate (1.5 g, 58 %). 1H NMR: (400 MHz, CDCl3) delta: 5.92-5.81 (m, 1H), 5.07-5.00 (m, 2H), 2.28 (d, J = 6.8 Hz, 2H), 1.45 (s, 9H), 1.15 (dd, J = 4.0, 3.2 Hz, 2H), 0.67 (dd, 4.0, 2.8 Hz, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 87661-20-9.

Reference:
Patent; CAVION, INC.; RICHARDSON, Thomas E.; HIGGIN, Michelle; MACDONALD, Timothy; (102 pag.)WO2018/152317; (2018); A1;,
Ester – Wikipedia,
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