Month: May 2021

Synthetic Route of 1268830-91-6, The chemical industry reduces the impact on the environment during synthesis 1268830-91-6, name is Methyl 3-amino-6-fluoro-2-methoxybenzoate, I believe this compound will play a more active role in future production and life.

A 250 mL round bottom flask was charged with a solution of methyl 3- amino-6-fluoro-2-methoxybenzoate (3.656 g, 18.36 mmol) in methylene chloride (100 mL). To this reaction mixture was added a solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) over a course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, 100 mL saturated aqueous sodium bicarbonate was added followed by stirring for 10 minutes. The aqueous mixture was extracted with 200 mL ethyl acetate (2x). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0-30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)benzoate as an oil (4.914 g, 85%). 1H NMR (400 MHz, DMSOd6) delta = 9.27 (s, IH), 7.48 (dd, J=9.1, 6.1, IH), 7.09 (t, J=9.0, IH), 3.89 (s, 3H), 3.85 – 3.74 (m, 3H), 3.29 (s, 15H).

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 3-amino-6-fluoro-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; WENGLOWSKY, Steven Mark; WO2011/25947; (2011); 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. 19063-56-0, name is 7-Bromo-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H5BrO2

2-Butyl-6-ethynyl-1H-benz [de]isoquinoline-1,3(2H)-dione 14(0.2 g, 0.722 mmol) and 7-Bromocoumarin (0.16 g, 0.722 mmol) weredissolved in THF-triethylamine (1:1, v/v, 120 mL) and the mixture wasdeaerated for 10 min by bubbling nitrogen gas. Then, Pd(PPh3)2Cl2(10.35 mg, 2 mol%), PPh3 (7.5 mg, 4 mol%) and CuI (2.75 mg, 2mol%)were added. The solution was deaerated for further 5 min; after that,the reaction was left for 8 h under nitrogen atmosphere at 60 C. Aftercompletion of the reaction, the reaction mixture was cooled to roomtemperature and the solvent was evaporated. The crude product wasdissolved in dichloromethane and purified by silica gel column chromatographywith chloroform as eluant. NC 5 was obtained in 60.2%yield (0.18 g), m. p. 252 C. IR (KBr): numax/cm-1 2200 (nuC?C) 1740(nuCO), 1693 (nuCO). 1H NMR (400 MHz, CDCl3) delta8.712 (d, 1H,J=8.40 Hz, aromatic),8.675 (d, 1H, J=7.2 Hz, aromatic),8.59 (d, 1H,J=7.6 Hz, aromatic),8.01 (d, 1H, J=7.60 Hz, aromatic), 7.882 (t, 1H,J=8 Hz, aromatic), 7.74 (d, 1H, J=9.2 Hz, aromatic), 7.62 (s, 1H),7.56-7.55 (m, 2H, aromatic), 6.49 (d, 1H, J=9.6 Hz, aromatic), 4.19(t, 2H, J=7.6 Hz, CH2), 1.77-1.69 (m, 2H, CH2), 1.49-1.41 (m, 2H,CH2), 0.99 (t, 3H, J=7.6 Hz, CH3). 13C (150 MHz, CDCl3) delta163.86,163.61, 160.08, 153.84, 142.59, 132.0, 131.72, 131.55, 131.26,130.23, 128.06, 128.01, 127.81, 127.74, 126.38, 125.70, 123.10,122.82, 119.87, 119.53, 117.60, 96.96, 89.34, 40.38, 30.19, 20.38,13.85. HRMS (m/z): [M+H] calculated for C27H20NO4:422.1392;Found: 422.1399.

The synthetic route of 19063-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, T. Sheshashena; Hwang, Jiyoung; Choi, Myung?Seok; Dyes and Pigments; vol. 158; (2018); p. 412 – 419;,
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Application of 24393-53-1,Some common heterocyclic compound, 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, molecular formula is C11H11BrO2, 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.

308 mg (0.26 mmol, 5 mol%) of tetrakis(triphenylphosphine)palladium are added to a solution of 2 g (5.34 mmol, 1.0 eq) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]urea and 1.6 g (6.4 mmol, 1.2 eq) of ethyl 4-bromocinnamate in 20 mL of an 8/2 mixture of dimethylformamide and of 2M potassium phosphate solution. The reaction mixture is stirred for 3 hours at 90C. The reaction is stopped by addition of 50 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.69 g of ethyl 3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylate in oil form are obtained. Yield = 75 %

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 3-(4-bromophenyl)acrylate, its application will become more common.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2006/18326; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2459-25-8, name is Methyl 2-naphthoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C12H10O2

General procedure: To a solution of methyl 4-methylbenzoate (6.0 g, 40mmol, 1.0 equiv) in toluene (200 mL) was added TMSCF3 (11.3 g, 80 mmol, 2.0 equiv) at room temperatureunder Ar. The reaction mixture was cooled to -78 oC, TBAF (4 mL, 1.0 M in THF, 0.1 equiv) was then added.After stirring for 0.5 h at -78 oC, the reaction mixture was allowed to warm to room temperature and stirred forfurther 12 h. Hydrochloric acid (30 mL, 2.0 M, 1.5 equiv) was then added and the resulting mixture stirred forfurther 2 h. The resulting suspension was quenched with saturated aqueous NaHCO3 and extracted with ethylacetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue waspurified by flash column chromatography to give ketone 10a.

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

Reference:
Article; Gao, Xing; Cheng, Ran; Xiao, Yu-Lan; Wan, Xiao-Long; Zhang, Xingang; Chem; vol. 5; 11; (2019); p. 2987 – 2999;,
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Application of 76308-26-4, A common heterocyclic compound, 76308-26-4, name is Ethyl 2-(trans-4-aminocyclohexyl)acetate hydrochloride, molecular formula is C10H20ClNO2, 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 solution of cyclohexyl-[5-fluoro-2-((_R)-methoxy-phenyl-methyl)-benzoimidazol-l- yl] -acetic acid (350 mg, 0.88 mmol, 1.0 equiv) in DMF (5 mL) was added triethylamine (179 mg, 240 muL, 1.77 mmol, 2.0 equiv) and HATU (403 mg, 1.06 mmol, 1.2 equiv) and the mixture stirred at 40 0C. After 15 min, trans- (4-amino-cyclohexyl) -acetic acid ethyl ester hydrochloride (235 mg, 1.06 mmol, 1.2 equiv; [CAS RN 76308-26-4]) was added and stirring continued at 50 0C for 2 h. The solution was concentrated by evaporation under reduced pressure, the pH adjusted to 9 by addition of a solution of 1 M NaHCtheta3 and the aqueous layer extracted with dichloromethane. The combined organic phases were dried over MgStheta4 and concentrated by evaporation under reduced pressure. The crude material was used in the consecutive step without further purification. MS (ISP): 564.7 [M+H]+.

The synthetic route of 76308-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BENSON, Gregory Martin; BLEICHER, Konrad; FENG, Song; GRETHER, Uwe; KUHN, Bernd; MARTIN, Rainer E.; PLANCHER, Jean-Marc; RICHTER, Hans; TAYLOR, Sven; WO2010/43513; (2010); A1;,
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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 13031-39-5 as follows. HPLC of Formula: C8H7ClO2

3-chlorophenyl acetate (starting material 2) was mixed with aluminium chloride (3 eq). The mixture was heated at 200 C. for 1 hour. The reaction medium was cooled to room temperature then poured in ice. The aqueous phase was extracted with methylene chloride which was dried on magnesium sulfate then vacuum evaporated. Purification was by silica gel chromatography (elution: cyclohexane/ethyl acetate 95:5). 1 H NMR CDCl3 deltappm: 3.41 (s, 3 H), 6.81 (dd, J=8.82 Hz, J=1.47 Hz, 1H), 6.91 (d, J=1.47 Hz, 1H), 7.60 (d, 8.82 Hz, 1 H), 12.33 (s, 1H) Reference: Chen et al, J Chem Soc, 1958, 146-148.

According to the analysis of related databases, 13031-39-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENFIT; US2005/171149; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

19063-56-0, name is 7-Bromo-2H-chromen-2-one, 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. name: 7-Bromo-2H-chromen-2-one

General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel).

The synthetic route of 19063-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sipos, Zoltan; Konya, Krisztina; Synlett; vol. 29; 18; (2018); p. 2412 – 2416;,
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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. 14659-60-0, name is Methyl 4-fluoro-2,6-dimethylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H11FO2

4-Amino-2,6-dimethyl benzoic acid (200 mg, 1.1 mmol) and NOBF4 (196 mg, 1.7 mmol) were heated in 1,2-dichlorobenzene at 100 C for 30 min. The solution was cooled and diluted with MeOH and water. A few pellets (2-3) of KOH were added, and the solution was heated at reflux for 16 h. The solution was concentrated. The residue was partitioned between Et2O and 1 N NaOH. The aqueous layer was extracted with Et2O. The aqueous layer was cooled to 0 C and acidified with conc. HCl (pH = 1-2). The aqueous layer was extracted with CH2Cl2. The organic layers were dried (Na2SO4). Filtration and concentration gave 58 mg (31 %) of the acid as a tan solid.

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 14659-60-0.

Reference:
Patent; SCHERING CORPORATION; EP1175401; (2005); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31273-66-2, name is Ethyl 2,3-dichlorobenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 31273-66-2, Safety of Ethyl 2,3-dichlorobenzoate

General procedure: A mixture of substituted ethyl benzoate (12a-g) (0.1M) and hydrazine hydrate (0.3M) was heated under reflux for 30min. Ethanol (20mL) was added to the refluxing mixture as a solvent in order to homogenize the solution, the resulting mixture was further allowed for 6h. Excess of ethanol was distilled out and the content was allowed to cool. The crystals formed were filtered and washed thoroughly with water and dried.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Rakse, Monika; Karthikeyan, Chandrabose; Deora, Girdhar Singh; Moorthy; Rathore, Vandana; Rawat, Arun K.; Srivastava; Trivedi, Piyush; European Journal of Medicinal Chemistry; vol. 70; (2013); p. 469 – 476;,
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Some common heterocyclic compound, 326-58-9, name is Benzo[d][1,3]dioxol-5-yl acetate, molecular formula is C9H8O4, 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. COA of Formula: C9H8O4

General procedure: (i) [Ir(coe)2Cl]2 (0.9 mg, 0.1mol %) and aryl acetates 1 (1 mmol) were added to a flame-dried, nitrogen-purged septum-capped vial. The mixture was dissolved with THF (0.3 mL, 3.3 M), and diethylsilane (0.26 mL, 2 mmol) was added to the mixture. The septum on the vial was replaced by a screw cap with a Teflon liner under a N2 atmosphere [note: diethylsilane (bp 56 C and density 0.686 g/mL) is volatile]. The reaction mixture was stirred for 3-12 h at 60 C. Volatiles were removed in vacuo to afford silyl acetals, which were directly used for subsequent reactions without further purification. (ii) [Rh(nbd)Cl]2 (1.8 mg, 0.4 mol %), tris(4-methoxyphenyl)phosphine (8.4 mg, 2.4 mol %), norbornene (188 mg, 2 mmol), and THF (1 mL, 1M) were added to the crude silyl acetals (1 mmol). The septum on the vial was replaced by a screw cap with a Teflon liner, and the mixture was stirred at 120 C for 15 min. The reaction progress was monitored by GC/MS spectrometry. The resulting benzodioxasilines 3 were directly used for a subsequent reaction without further purification. For hindered substrates 3o-r, the resulting benzodioxasilines 3 were purified for the subsequent reactions; volatiles were removed in vacuo, and the resulting mixture was dissolved with pentane, filtered through a pad of Celite, and concentrated in vacuo. The crude product was purified by MPLC (hexanes/EtOAc=80:1, 5mL/min, retention time 5-15 min). (iii) The crude benzodioxasilines 3 (1 mmol, THF, 1M) were diluted with diethyl ether (3 mL, 0.33 M) and cooled to -78 C. MeLi (3 mmol, 1.6 M in Et2O) were added into the reaction mixture at -78 C and stirred for 1 min. (iv) Trifluoromethanesulfonyl anhydride (1.2 mmol, 0.2 mL) was added into the reaction mixture. The reaction mixture was warmed to rt and stirred for 30 min. The reaction mixture was cooled to 0 C and saturated aqueous ammonium chloride solution was added. The mixture was extracted with diethyl ether three times. The combined organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. Volatiles were removed in vacuo, and the crude mixture was purified by MPLC to afford arylsilyl triflates 5 (hexanes/EtOAc=40:1, 5mL/min, retention time 6-20 min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 326-58-9, its application will become more common.

Reference:
Article; Asgari, Parham; Dakarapu, Udaya Sree; Nguyen, Hiep H.; Jeon, Junha; Tetrahedron; vol. 73; 29; (2017); p. 4052 – 4061;,
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Ester – an overview | ScienceDirect Topics