Category: 154825-97-5

154825-97-5, 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. 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, A new synthetic method of this compound is introduced below.

Example 72C; methyl 2-{4-[(7-amino-5-methyl[l,2,4]triazolo[l,5-alpha]pyrimidin-6-yl)ethynyl]phenyl}-2- methylpropanoate A mixture of Example 72B (17 mg, 0.1 mmol), methyl 2-(4-bromophenyl)-2- methylpropanoate (38 mg, 0.15 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.5 mg, 0.005 mmol), CuI (1 mg, 0.005 mmol), and triethylamine (28 muL, 0.2 mmol) in acetonitrile (500 muL) was heated at 95 0C under nitrogen for 1 h. The resulting mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuuo. The residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate) to provide the title compound as a white solid (16 mg, 45% yield). 1H NMR (300 MHz, DMSO-J6) delta 8.44 (s, 3 H), 7.64 (d, J = 8.48 Hz, 2 H), 7.36 (d, J= 8.48 Hz, 2 H), 3.61 (s, 3 H), 2.60 (s, 3 H), 1.52 (s, 6 H). MS (ESI) m/z 350 (M+H)+.

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; ABBOTT LABORATORIES; WO2008/134690; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

154825-97-5, 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. 154825-97-5 name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, 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.

To a 50 mL two neck flask were added methyl 2- (4-bromophenyl) -2-methylpropionate (689 mg, 2.68 mmol) , (R) -tert-butyl 3-oxohexahydroimidazo [1, 5-a] pyrazine-7 (1H) -carboxylate (630 mg, 2.61mmol) , Pd2(dba)3(180 mg, 0.19 mmol) , 2-di-tert-butylphosphino-2′, 4′, 6′-triisopropylbiphenyl (550 mg, 1.26 mmol) , Cs2CO3(173 mg, 0.53 mmol) and 1, 4-dioxane (25 mL) , the mixture was stirred at 90 for 12 hours. After the reaction was completed, the mixture was cooled to rt and filtered. The filter cake was washed with EtOAc (25 mL) . To the filtrate were added EtOAc (75 mL) and water (50 mL) , the mixture was shaken and separated into layers. The water layer was extracted with ethyl acetate (50 mL) . The combined organic phases were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (V/V) = 1.2/1) to give the title compound as a white solid (200 mg, 17.88%) . MS (ESI, pos. ion) m/z: 440.1 [M+Na]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, molecular formula is C11H13BrO2, 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. 154825-97-5.

EXAMPLE 12; 4 -R (1S)-1-[[(1S)-1-[[(1-cyanocyclopropyl)amino]carbonyl]-3-fluoro-3-methylbutyl]amino]-2,2,2- TRIFLUOROETHYLL-A, CT-DIMETHYL- (1, 1 -BI HENVLL-4-ACETIC acid; STEP 1 : 2- (4-BROMOPHENYL)-2-METHYLPROPANOIC acid; To a 0 C solution of diisopropylamine (1.52 mL) in THF (50 mL) was slowly added butyllithium (4.3 mL). The reaction mixture was stirred at 0 C for 15 minutes. It was cooled to-78 C and a solution of methyl 2- (4-bromophenyl) propanoate from Example 11 Step 2 (2.4 g) in THF (25 ML) was slowly added. The mixture was stirred at-78 C for 30 minutes. Then a solution of iodomethane (2.5 mL) in THF (25 mL) was added dropwise and the mixture was stirred at-78 C for 30 minutes then warmed up slowly to room temperature and stirred for 1 HOUR. H NMR showed 50% conversion. The reaction mixture was cooled to 0 C and 20 mL of potassium t-butoxid (1.0 M in THF) was added dropwise. The mixture was stirred at 0 C for 30 minutes, warmed up to room temperature and stirred for 1 hour. The reaction mixture was poured into ice (50 g) and saturated aqueous ammonium chloride (100 mL), extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo to yield a residue which was diluted with THF (30 ML) and methyl alcohol (15 mL). The solution was cooled to 0 C and 20 mL of lithium hydroxide (1.0 N) was added. The mixture was stirred at room temperature for 3 hours. Then the reaction mixture was poured into ice and 1N HC1 and extracted with dichloromethane (2 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound. ‘H NMR (CD3COCD3) 8 10.85 (1H, bs), 7.53 (2H, d), 7.48 (2H, d), 1.50 (6H, s).

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

Reference:
Patent; MERCK FROSST CANADA & CO.; WO2005/19161; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

154825-97-5, Name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, 154825-97-5, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: A mixture of bromobenzene (10 g, 63.6 mmol), acetic acid (5.76 g, 96 mmol), methylamine (3.0 g-100% basis, 95.5 mmol) of 40% solution, and Cu powder (2.01 g) followed by DMF (20 mL) was heated at reflux in a 100 mL round bottom flask for 9 h. The mixture was cooled to rt, dichloromethane (200 mL) was added and then filtered to remove Cu powder. The filtrate was washed with water (200 mL) and dried over sodium sulphate and concentrated under reduced pressure. Crude sample thus obtained was purified by column chromatography (silica gel, ethyl acetate/petroleum ether, 5:95) to give N-methyl aniline (3.74 g, 55%, 1c).

Statistics shows that Methyl 2-(4-bromophenyl)-2,2-dimethylacetate is playing an increasingly important role. we look forward to future research findings about 154825-97-5.

Reference:
Article; Siddegowda, Maravanahalli S.; Yathirajan, Hemmige S.; Ramakrishna, Ramesha A.; Tetrahedron Letters; vol. 53; 39; (2012); p. 5219 – 5222;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics