Category: 1236357-65-5

Synthetic Route of 1236357-65-5,Some common heterocyclic compound, 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, molecular formula is C12H13BrO2, 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 mixture of 2-aminopyrimidine-5-boronic acid pinacol ester (221 mg, 1.0 mmol), I- 36 (200 mg, 0.74 mmol), Pd-FibreCat-1007 (75 mg, 0.045 mmol) in THF (2.0 mL) at room temperature is added 2M Na2C03 solution (0.75 mL). The mixture is heated in the microwave at 120 C for 30 minutes, allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with brine, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-100% EtOAc in heptane) to give 1-37 (75 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
Ester – Wikipedia,
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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 1236357-65-5 as follows. Product Details of 1236357-65-5

To degassed toluene (25 mL) was added palladium acetate (18 mg, 0.0825 mmol) and Xphos (79 mg, 0.165 mmol) and the mixture was degassed a further 30 minutes. To this reaction mixture was added methyl 1-(4-bromophenyl)cyclobutanecarboxylate (900 mg, 3.3 mmol) and cesium carbonate (3.2 g, 9.9 mmol) and this was degassed for a further 10 minutes. Beta-alanine ethyl ester (920 mg, 6.6 mmol) and diisopropylethyl amine (1.1 ml, 6.6 mmol) were added and this was brought to reflux and stirred overnight. The reaction was cooled to room temperature and poured onto water (100 ml). It was then extracted with ethyl acetate (2*100 ml), dried over magnesium sulfate, filtered, and evaporated to give methyl 1-(4-(3-ethoxy-3-oxopropylamino)phenyl)cyclobutanecarboxylate. Taken on crude to the next reaction. 1H NMR (400 MHz, CDCl3) 7.1 (d, 2H), 6.55 (d, 2H), 4.15 (m, 2H), 3.65 (s, 3H), 3.45 (m, 2H), 2.75 (m, 2H), 2.60 (t, 2H), 2.45 (m, 2H), 1.95 (m, 1H), 1.85 (m, 1H), 1.35 (m, 3H)

According to the analysis of related databases, 1236357-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; pfizer Inc; US2010/197591; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 1-(4-bromophenyl)cyclobutanecarboxylate

Methyl 1-(4-bromophenyl)cyclobutanecarboxylate under nitrogen atmosphere(1.3 g, 4.8 mmol), (R)-3-oxo hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylic acid tert-butyl ester (1.2 g, 4.8 mmol),Tris(dibenzylideneacetone)dipalladium(440mg, 0.48mmol),2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (410 mg, 0.97 mmol) and cesium carbonate (3.1 g, 9.5 mmol) were dissolved.In 1,4-dioxane (30 mL). The reaction was carried out at 90 C for 12 h.The heating was stopped, the solid was filtered off, and the filtrate was concentrated under reduced pressure.The residue obtained was subjected to silica gel column chromatography(PE/EA(V/V)=4/1)Purified to give the title compound as a white solid(770 mg, 37%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Liu Xinchang; Huang Jianzhou; Zhang Yingjun; S ·geerdeman; (267 pag.)CN109111451; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, molecular formula is C12H13BrO2, 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. name: Methyl 1-(4-bromophenyl)cyclobutanecarboxylate

Step 1. Methyl l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)cyclobutane-l -carboxylate: Into a 40 ml vial equipped with a magnetic stir bar and under N2 were added 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2- dioxaborolane (2.26 g, 8.92 mmol), methyl l-(4-bromophenyl)cyclobutanecarboxylate (2 g, 7.43 mmol), Pd(dppf)C12, complex with DCM (307.18 mg, 371.56 muiotatauiotaomicron) and potassium acetate (2.19 g, 22.29 mmol). The vial was evacuated under vacuum and refilled with N2. DMF (15 mL) was added, and the mixture was degassed for 10 minutes with N2 and then heated to 100 C O/N. The black reaction mixture was cooled to RT, and purified by column chromatography through silica gel eluting with 100:0 to 0: 100 Hexanes:EtOAc as a gradient over 25 minutes. The desired fractions were combined, concentrated and further dried under high vacuum O/N to provide a yellow solid (1.6 g) LCMS (ESI+) m/z = 317 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1236357-65-5, its application will become more common.

Reference:
Patent; TEMPEST THERAPEUTICS, INC.; POWELL, David Andrew; ROPPE, Jeffrey Roger; SEIDERS, Thomas Jon; DING, Jinyue; SHENG, Tao; JACINTHO, Jason Duarte; (65 pag.)WO2019/79614; (2019); 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. 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H13BrO2

To a 25 mL round-bottom t1ask purged with and maintained under an inertatmosphere of nitrogen was added (1 S,4S,5R)-.5-[ [ 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2- oxazol-4-yl]methoxy ]-2-az.abicyclo[ 2.2.l]heptane hydroiodide salt l2dd (200 mg, 0.3943rnmol, 1.00 equiv.), Tol (lO mL), methyll-(4-bromophenyl)cyclobui:me-1-carboxylate 150b(212 mg, 0.79 mmol, 2.0 equiv.), Ru-Phos-Precatalyst (89 mg, 0.10 mmol, 0.25 equiv.),RuPhos (89 mg), and Cs2C01 (516 mg, 1.58 mmol, 4.00 equiv.). The resulting mixture was5 stirred at ll 0 C overnight and concentrated under vacuum. The residue vvas puriiled bysilica gel column chromatography eluting with ethyl acetate/petroleum ether (l/5) to affordmethyl 1-[4-[ (l S,4S,5R)-5-[ [ 5-cyclopropyl-3-(2,6-dichlorophenyl)- L2-oxazol-4-y l]methoxy ]-2-azabicydo[2.2.1]heptan-2-yl]pheny l]cyclobutane-1-carboxy late 150c (140rng, 63~”0) as a light yellow oil.

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 1236357-65-5.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics