Esters-buliding-blocks

Electric Literature of 344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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.

Example 224 Synthesis of dimethyl 2-((2-((4-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)methyl)-2-fluoromalonate. To a solution of compound dimethyl 2-fluoromalonate (0.54 g, 3.6 mmol) in anhydrous DMF (10 mL) was added NaH (140 mg, 3.6 mmol, 60% in mineral oil) and the reaction was stirred at 0 C. for 0.5 h under N2 atmosphere. Then the solution of tert-butyl 1-((8-(chloromethyl)-6-cyclopropylimidazo[1,2-a]pyridin-2-yl)methyl)-1H-1,2,3-triazole-4-carboxylate (1 g, 2.5 mmol) in DMF (2 mL) was added, The resulting mixture was stirred at 80 C. for 16 h. The reaction was quenched with saturated aqueous NH4Cl solution (20 mL), and extracted with ethyl acetate (100 mL*2). The combined organic phases were dried over Na2SO4, evaporated to give the crude, which was purified with silica gel chromatography (DCM/MeOH=100/1) to give the dimethyl 2-((2-((4-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)methyl)-2-fluoromalonate (1.1 g, 85%) as a yellow solids. ESI-MS [M+H]+: 502.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2-fluoromalonate, its application will become more common.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
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Electric Literature of 2967-66-0, 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. 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

Several other esters, whose structure and names are described in Table 3, were hydro genated under the conditions described above using preformed RuCl2(L-I). Isolated yield are given in Table 4.Table 3: Structure and names of substrates usedTable 4: Hydrogenation of esters using RuCl2(L-I) EPO Sub.: Substrate as described in Table 3.Conv.: Conversion (in %, analysed by GC after silylation) of ester to alcohol after 2h30min.Reaction conditions: Substrate (20 mmol), H2 gas (50 bars), RuCl2(L-I) 0.05 mol%,NaOMe 10 mol%, THF (14 mL) at 1000C during 2h 30min.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-(trifluoromethyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FIRMENICH SA; WO2006/106484; (2006); A1;,
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Synthetic Route of 35613-44-6, 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. 35613-44-6, name is Methyl 2-(2-aminophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 7.2 g of 4-chloro-7-trifluoromethylquinoline, 5.4 g of methyl 2- aminophenylacetate and 250 mL of acetonitrile is heated under reflux for 18 hours. The solvent is evaporated under reduced pressure and the residue extracted 3 times with 200 mL portions of hot water. The aqueous extract is rendered basic with 10% ammonium hydroxide whereupon the desired compound precipitated; it was recrystallized from aqueous ethanol yielding colorless needles with a melting point of 140-1410C.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(2-aminophenyl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MILESTONE PHARMACEUTICALS INC.; WO2008/48577; (2008); 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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, A new synthetic method of this compound is introduced below., COA of Formula: C9H9BrO2

Dissolve NaH (140mg, 3.50mmol, 60mass%) under nitrogen protectionN,N-dimethylformamide (10 mL) was added to it under ice bathMethyl 2-(4-bromophenyl)acetate (200 mg, 0.87 mmol),After stirring for 30 min, iodomethane (0.33 mL, 5.2 mmol) was added.The reaction was allowed to warm to room temperature and stirred for 12 h.The reaction was quenched with water (20 mL), EtOAc (EtOAc)Wash with saturated brine (50 mL), dryThe title compound was obtained as a colorless oil (150 mg, 67%).

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;,
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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 17100-63-9 as follows. Safety of Methyl 4-bromo-3-methoxybenzoate

A suspension of methyl 4-bromo-3-methoxybenzoate (2.5 g; 10.2 mmol; 1.00 eq.), 4-methyl-3- thiopheneboronic acid (Aldrich 542393; 1.59 g; 11.2 mmol; 1.1 eq.), potassium carbonate (7.05 g; 51 mmol; 5 eq.) and Pd(PPh3)4 (1.18 g; 1 mmol; 0.1 eq.) in toluene (12.5 ml_) and water (12.5 ml.) was refluxed for 5 hours. The reaction mixture was cooled down to room temperature and filtered through a pad of celite which was further washed with touene (200 ml_). The filtrate was concentrated in vacuo and the residue taken up in Ethyl acetate (400 ml_). The organic layer was washed with sat. aq. NaHCC>3 (100 ml_), water (100 ml_) and brine (100 ml_) then dried over magnesium sulfate and concentrated in vacuo. The residue (2.3 g; 8.77 mmol; 1 eq.) was taken up in EtOH (69 ml_), sodium hydroxide (5M; 5.26 ml 26.3 mmol; 3 eq.) was added and the reaction mixture was stirred at 6O0C for one hour. After concentration in vacuo, the residue was taken up in water (200 ml_) and the aqueous phase was washed with Ethyl acetate then acidified to pH 2 with cone. HCI. The solution was concentrated to ca. 100 ml_ and the precipitate filtered off and dried to afford the title compound (1.81 g, 71 %) as a brown solid. HPLC (Method A) : Rt 3.99 min (purity 97.4%). LC/MS : 246.9 (M-H)”.

According to the analysis of related databases, 17100-63-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 23786-14-3, name is Methyl 4-methoxyphenylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H12O3

NBS (9.06 g, 50.90 mmol) and AIBN (398 mg, 2.43 mmol) was added into a solution 2-(4-methoxyphenyl)acetate17(8.74 g, 48.50 mmol) in carbon tetrachloride (50 ml). The reaction was refluxed at 80Cfor 4h and quenched with water. Carbon tetrachloride was removed under vacuum. The reaction was extracted with ethyl acetate. The organic phase was washed with sodium thiosulfate (1M) and then saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated to obtain the crude product18(12.43 g, 99% yield) as a white solid.1H NMR (400 MHz, CDCl3) delta 7.52-7.45 (m, 2H), 6.91-6.85 (m, 2H), 5.35 (s, 1H), 3.81 (s, 3H), 3.79 (s, 3H).

The synthetic route of 23786-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Guangzhe; Dong, Huijuan; Ma, Yao; Shao, Kun; Li, Yueqing; Wu, Xiaodan; Wang, Shisheng; Shao; Zhao, Weijie; Bioorganic and Medicinal Chemistry Letters; vol. 29; 16; (2019); p. 2327 – 2331;,
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Some common heterocyclic compound, 176694-36-3, name is Methyl 4-fluoro-3-(trifluoromethyl)benzoate, molecular formula is C9H6F4O2, 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. HPLC of Formula: C9H6F4O2

3-Fluoroazetidine hydrochloride (1 10 mg, 0.99 mmol), /V,/V-diisopropylethylamine (0.34 ml_, 1.98 mmol) and methyl 4-fluoro-3-(trifluoromethyl)benzoate (200 mg, 0.90 mmol) were heated to 65 C in dimethyl sulfoxide (1 ml.) for 4 hours, by which time the starting material appeared to have been consumed by TLC. STEP 2: The reaction mixture was then concentrated under reduced pressure and the crude residue was dissolved in toluene (1 ml.) and ethanol (1 ml_). Hydrazine monohydrate (0.17 ml_, 3.60 mmol) was then added and the reaction mixture was heated at 65 C for 16 hours, by which time the starting material appeared to have been consumed by TLC. The reaction mixture was then concentrated under reduced pressure and the crude residue was recrystallised from cyclohexane and diethyl ether to give crude 4-(3- fluoroazetidin-1 -yl)-3-(trifluoromethyl)benzohydrazide (82 mg, 0.30 mmol, 33% yield) as a yellow solid that was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 176694-36-3, its application will become more common.

Reference:
Patent; UCL BUSINESS LTD; FISH, Paul, Vincent; MAHY, William; WILLIS, Nicky, John; WOODWARD, Hannah; ATKINSON, Benjamin, N; BAYLE, Elliott, D; SIPTHORP, James; JONES, Edith, Yvonne; ZHAO, Yuguang; VECCHIA, Luca; RUZA, Reinis, Reinholds; (208 pag.)WO2020/43866; (2020); A1;,
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Electric Literature of 3618-04-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (10.32 g, 59.92 mmol) in dimethylformamide (50 mL) was added imidazole (8.16 g, 119.8 mmol), followed by tert-butyldimethylsilyl chloride (9.94 g, 65.9 mmol). The resulting mixture was stirred at room temperature for 16 hours. Diethyl ether was added (150 mL), and the mixture was washed with 1M [HC1] (150 mL). The aqueous layer was extracted with diethyl ether (150 mL). The combined organic layers were washed with 1M [HC1] (100 mL) and saturated sodium chloride solution (100 mL), dried over magnesium sulfate, filtered and concentrated to afford a clear oil. MS (CI) m/z 287 (M+1) [+]

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
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Synthetic Route of 73368-41-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 73368-41-9, name is Ethyl 4-amino-3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

After adding acetonitrile (170 mL) and N-chlorosuccinimide (13.4 g, 100 mmol) to ethyl 4-amino-3-methoxybenzoate (17.8 g, 91.2 mmol) in that order, the mixture was stirred at 60 C. for 2 hours. The mixture was returned to room temperature, and the solvent in the mixture was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=8/1 then 4/1) to obtain the title compound (15.8 g, 68.8 mmol). 1H-NMR (CDCl3) delta: 1.37 (t, J=6.8 Hz, 3H), 3.91 (s, 3H), 4.32 (q, J=6.8 Hz, 2H), 4.58 (br.s, 2H), 7.36 (d, J=1.8 Hz, 1H), 7.65 (d, J=1.8 Hz, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 4-amino-3-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R & D Management Co., Ltd.; US2009/259049; (2009); A1;,
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Application of 15568-85-1, 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 15568-85-1 as follows.

General procedure: 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (0.5 g, 2.9 mmol) was added to a stirred solution of the 5-aminopyrazole 6 (2.9 mmol) in MeCN (10 mL). After stirring for 1 h, the solvent was removed in vacuo to complete the precipitation of the product.

According to the analysis of related databases, 15568-85-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mackay, Martha; Nortcliffe, Andrew; McNab, Hamish; Hulme, Alison N.; Synthesis; vol. 47; 2; (2015); p. 242 – 248;,
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