Tag: M.W=200-300

Application of 3469-00-9,Some common heterocyclic compound, 3469-00-9, name is Methyl Diphenylacetate, molecular formula is C15H14O2, 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.

2,2-Diphenylacetohydrazide To a stirred solution of methyl 2,2-diphenylacetate (0.5 g, 1 equiv) in anhydrous EtOH (150 mL) was added hydrazine hydrate (8 mL) and heated to reflux. Stirring was then continued for 1 hour. The reaction mixture was then cooled and the solvents removed under reduced pressure. The crude oil was diluted with EtOAc and washed with H2O and the organic phase dried over Na2SO4, filtered, and the solvents removed under reduced pressure to yield a yellow oil (0.97 g, 97%) that was used without further purification.

The synthetic route of 3469-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Omeros Corporation; US2010/35872; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 40876-98-0, 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 40876-98-0 as follows.

General procedure: A mixture of 1a (218 mg, 1.0 mmol) and 2a (231 mg, 1.1 mmol) in DMF (1.5 mL) was stirred at room temperature for 12 h. After the usual aqueous extractive workup and column chromatographic purification process (hexanes/CH2Cl2/EtOAc, 10:1:1), compound 3a was obtained as colorless oil, 183 mg (53%) along with 5a (43 mg, 17%). Other compounds were synthesized similarly, and the spectroscopic data of 3a, 5a, 6a, 3d,3f and 3h are as follows.

According to the analysis of related databases, 40876-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yu, Jin; Kim, Ko Hoon; Lee, Hyun Ju; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 34; 10; (2013); p. 3027 – 3032;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 150529-73-0, 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. 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

Tributyltin methoxide (28.3 mL, 98 mmol), the product of preparation 17 (15.0 g, 65mol), isopropenyl acetate (10.8 mL, 98 mmol), palladium (ll) acetate (750 mg, 3.30 mmol) and tri-ortho-tolylphosphine (2.0 g, 6.5 mmol) were stirred together in toluene (75 mL) at 100 C for 5 hours. After cooling, the reaction was diluted with ethyl acetate (150 mL) and 4M aqueous potassium fluoride solution (90 mL), and stirred for 15 minutes. The mixture was filtered through Arbocele and the organic phase was separated and concentrated in vacuo. The residue was then purified by column chromatography on silica gel eluting with diethyl ether : pentane, 0: 100 to 25: 75, followed by dichloromethane to give the title compound as a pale yellow oil in 94% yield (12.6 g). H NMR (400MHz, CDCI3) : 8 : 2. 15 (3H, s), 3.61 (2H, s), 3.69 (5H, s), 7.10-7. 13 (2H, m), 7.19 (1H, d), 7.30 (1H, t); LRMS ESI : m/z 229 [M+Na] +

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(3-bromophenyl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/92840; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, molecular formula is C9H9BrO2, 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.

(2) Compound 2 (4.0 g), Compound 3(3.52 g),[1,1′-bis (diphenylphosphino) ferrocene] palladium (II)Dichloromethane adduct (1.43 g)And potassium carbonate (7.24 g)Of N, N-dimethylformamide (80 mL)Under a nitrogen atmosphere,And the mixture was stirred at 80 C. for 6 hours.To the reaction mixture was added diethyl ether (200 mL)And the mixture was stirred, and insoluble matter was removed by filtration.Water and ethyl acetate were added to the filtrate, followed by stirring,And extracted with ethyl acetate.The obtained organic layer was washed with water and saturated brine,Dried and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5 to 80:20) to obtain Compound 4 (2.78 g) As a pale yellow viscous substance.

The synthetic route of 87808-49-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma; Sato, Atsushi; Imashiro, Ritsuo; Tuzisima Tosinori, Shuichi; Tanimoto, Koichi; Yamamoto, Yasuo Wang; Nakane, Tetsuya; Erikawa, Chihiro; (123 pag.)JP2018/199673; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 29547-04-4, A common heterocyclic compound, 29547-04-4, name is Methyl 2,4-dibromobutanoate, molecular formula is C5H8Br2O2, 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 stirred solution of N1,N2-dibenzylethane-1,2-diamine (11.20 g, 46.60 mmol) and TEA (13.00 mL, 93.20 mmol) in toluene (80 mL) was added the solution of methyl 2,4- dibromobutanoate (12.10 g, 46.60 mmol) in toluene (110 mL) dropwise at RT. The reaction mixture was stirred for 16 hours at 80C. The resulting mixture was poured into aqueous sat?d Na2CO3 solution (60 mL) and extracted with EA (3 x 50 mL). The combined organic layers were washed with brine (3 x 80 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under vacuum. The residue was purified by a silica gel column chromatography, elutingwith 20% EA in PE to afford the title compound: LCMS [M + 1]+: 339.

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.; PASTERNAK, Alexander; DONG, Shuzhi; SCOTT, Jack, D.; TANG, Haiqun; ZHAO, Zhiqiang; YANG, Dexi; GU, Xin; JIANG, Jinlong; XIAO, Li; (209 pag.)WO2019/18186; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 29823-21-0, 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 29823-21-0 as follows.

To a solution of sodium ethoxide (1.422 g, 20.9 mmol) in EtOH (10 mL) was added diethyl acetonedicarboxylate (4.23 g, 3.800 mL, 20.9 mmole). The stirred solution was heated to the reflux temperature, and then ethyl 8-bromooctanoate (XD-013-19, 5.24 g, 20.9 mmol) was added slowly. Stirring and heating were continued for two hours. After another solution of sodium ethoxide (20.9 mmole in 10 mL of EtOH) was added at reflux temperature, another 20.9 mmole of ethyl 8-bromooctanoate was added dropwise. The mixture was heated and stirred for 16 hours after addition was complete. Most of the ethanol was removed under reduced pressure. To the residue were added water (70 mL) and ether (250 mL). Saturated NH4C1 solution was added to adjust to pH 7. The two layers were separated. The ethereal solution was washed again with dilute NH4C1, brine. Concentration led to a brownish oil (11.44 g). The oil was hydrolyzed by boiling for 18 hours with a mixture of concentrated hydrochloric acid (21 mL) and glacial acetic acid (10.5 mL). The hydrolysis mixture was evaporated to dryness under reduced pressure, and the solid residue was washed with water and was crystallized from acetone. The product was dried well and was obtained as a pale solid (1.74 g).

According to the analysis of related databases, 29823-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALNYLAM PHARMACEUTICALS, INC.; ANSELL, Steven, Michial; DU, Xinyao; WO2013/86322; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 52727-57-8, 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 52727-57-8 as follows.

a) Methyl 2-amino-5-cyanobenzoate b) Methyl 2-amino-3-ethyl-5-cyanobenzoate A mixture of methyl 2-amino-5-bromobenzoate (4.6 g, 20 mmol), and CuCN (1.97 g, 22 mmol) in NMP (20 mL) was heated to 190 C. and 3 h. The reaction mixture was poured into a solution of ethylene diamine 4 mL) in H2O(16 mL) and extracted with toluene (4*20 mL). The extracts were dried (Na2SO4). Removal of the solvent gave the title compound a) (i.e., R8 is hydrogen). Use of methyl 2-amino-5-bromo-3-ethyl bromobenzoate gave the title compound b) (iLe., R8 is ethyl).

According to the analysis of related databases, 52727-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bi, Yingzhi; Yu, Guixue; Rotella, David P.; Macor, John E.; US2002/177587; (2002); 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. 223519-11-7, name is Methyl 3-amino-5-bromo-4-methylbenzoate, A new synthetic method of this compound is introduced below., Formula: C9H10BrNO2

4.2.1 Methyl 4-bromo-1H-indazole-6-carboxylate (13) To a stirred solution of amine 12 (4.50 g, 18.4 mmol) in acetic acid (80 mL), was added a solution of sodium nitrite (1.39 g, 20.3 mmol) in water (8 mL). The mixture was stirred overnight and then concentrated under reduced pressure. The residue was diluted with saturated sodium hydrogen carbonate (100 mL), extracted with ethyl acetate (3*30 mL) and the combined organic extracts were subject to standard workup. The crude product was recrystallised from toluene and the mother liquors were purified by flash chromatography (15% EtOAc/hexanes) to afford the indazole 13 (3.38 g, 72%) as a pale orange solid; Rf (15% EtOAc/hexanes) 0.25; mp 173-174 C; deltaH (DMSO-d6): 13.83 (1H, br s), 8.16 (2H, s), 7.78 (1H, d, J 1.0 Hz), 3.90 (3H, s); deltaC (DMSO-d6): 165.3, 139.7, 133.4, 128.4, 125.9, 122.6, 113.2, 111.9, 52.5; m/z (ESI): 254.9 (M[79Br]H+), 256.9 (M[81Br]H+); HRMS (ESI): M[79Br]H+, found 254.9765. C9H8BrN2O2 requires 254.9769.

The synthetic route of 223519-11-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Brzozowski, Martin; O’Brien, Nathan J.; Wilson, David J.D.; Abbott, Belinda M.; Tetrahedron; vol. 70; 2; (2014); p. 318 – 326;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 653-92-9, The chemical industry reduces the impact on the environment during synthesis 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, I believe this compound will play a more active role in future production and life.

[000106] To a stirred solution of methyl 2-bromo-4-fluorobenzoate 36 (2 g, 8.58 mmol) in 1,4- dioxane (50 mL) under inert atmosphere were added (4-methoxyphenyl) methanethiol 8 (1.58 g, 10.25 mmol), cesium carbonate (4.18 g, 12.80 mmol) at RT and purged under argon atmosphere for 30 mm. To this was added Pd(dppf)2C12 (306 mg, 0.42 mmol); heated to 120 C and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 250 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 7% EtOAc/ hexanes to afford compound 37 (1.6 g, 61%) as an off-white solid. TLC: 10% EtOAc/ hexanes(R 0.4); 1H NMR (CDC13, 400 MHz): oe 8.01 (dd, J 8.7, 6.2 Hz, 1H), 7.34 (d, J 7.9 Hz, 2H), 7.04 (dd, J= 10.3, 2.4 Hz, 1H), 6.88-6.80 (m, 3H), 4.09 (s, 2H), 3.88 (s, 3H), 3.80 (s, 3H).

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, Methyl 2-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 176694-36-3, 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. 176694-36-3 name is Methyl 4-fluoro-3-(trifluoromethyl)benzoate, 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.

EXAMPLE 8: (S)-4-[[4-[(3,4-Dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylmethyl- sulfanyl]-3-(trifluoromethyl)benzoic acid methyl ester. A solution of (S)-[4-[(3,4-dichlorophenyl)methyl]morpholin-2- yljmethylcarbamoylmethylsulfanylsodium (Preparation 6) (0.104 g) in DMF (1.0 mL) was added to a stirred solution of methyl-4-fluoro-3-(trifluoromethyl)benzoate (0.080 g) in DMF (0.5 mL) at room temperature and stirred for 16 h. The reaction mixture was then quenched with aqueous sodium bicarbonate and was extracted into DCM (10 mL x 3). The organic layers were combined and washed with water and dried over magnesium sulfate, filtered and concentrated to yield a pale oil which was chromatographed (SiO2: eluent gradient DCM to 5 : 95 methanol/DCM) to yield the subtitle compound as a colourless oil (0.09O g).MS (ES+ve) 551/553 [M+H]+; Retention time: 2.69 min (STANDARD).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-fluoro-3-(trifluoromethyl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2007/11292; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics