Tag: M.W=200-300

24398-88-7, A common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, molecular formula is C9H9BrO2, 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.

1-(6-(dibutyl(3-(ethoxycarbonyl)phenyl)stannyl)hexyl)-3-ethyl-1H-imidazol-3-ium bromide I’a-14(Br-) A dried 50 mL Schlenk tube was flushed with argon and charged with zinc dust (1.36 g, 20.8 mmol, 5 eq) and cobalt(II) bromide (0.095 g, 0.4190.434 mmol, 0.1 eq). The mixture was activated under vacuum at 150C during 4 h. Acetonitrile (5 mL) was added to the cooled mixture then trifluoroacetic acid (0.15 mL) and 1,2-dibromoethane (0.1 mL) were added and the resulting solution stirred for additional 15 minutes (an increase of temperature was observed). Then ethyl 3-bromobenzoate (1.46 g, 6.36 mmol, 6.3 eq) was introduced to the mixture which was stirred at room temperature for 12 h. The resulting solution of arylzinc reagent was introduced dropwise to the ionic liquid (Va-1) (529 mg, 1.0 mmol, 1 eq) in solution in THF (6 mL). After 18 h of stirring at room temperature, the resulting mixture was filtered through a short pad of silica gel then extracted with CH2Cl2 (3 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (CH2Cl2 to CH2Cl2/MeOH 90:10) to afford compound I’a-14(Br-) as viscous yellow oil (450 mg, 70 %). 1H NMR (CDCl3): delta 10.17 (s, 1H), 8.14 (bs, 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.62 (d, J = 7.2 Hz, 1H), 7.39 (dd, J = 7.5 Hz, J = 7.5 Hz, 1H), 7.30 (bs, 1H), 7.23 (bs, 1H), 4.48-4.33 (m, 4H), 4.32 (t, 2H, J = 7.2 Hz), 1.89-1.78 (m, 2H), 1.61-1.47 (m, 9H), 1.42-1.24 (m, 11H), 1.13-1.00 (m, 6H), 0.87 (t, J = 7.2 Hz, 6H). 13C NMR 75 MHz (CDCl3) delta (ppm): 166.8, 141.9, 140.6, 136.9, 135.9, 129.4, 128.8, 127.5, 122.0, 121.8, 60.6, 49.8, 45.1, 33.4, 30.0, 28.7, 27.0, 26.3, 25.5, 15.5, 14.4, 13.4, 9.4, 9.3. HRMS (FAB) calcd. for C28H47N2O2Sn 563.2654 [M-Br]+; found 563.2675.

The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Centre National de la Recherche Scientifique (CNRS); UNIVERSITE DE NANTES; UNIVERSITE D’ANGERS; Universite du Maine; Institut National de la Sante et de la Recherche Medicale (INSERM); Centre Hospitalier Universitaire De Nantes; Legoupy, Stephanie; Faye, Djibril; Gestin, Jean-Francois; Rajerison, Holisoa; Faivre-Chauvet, Alain; Boeda, Fabien; EP2891657; (2015); A1;,
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These common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, 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. 24398-88-7

General procedure: To an undivided electrochemical cell, fitted with an iron/nickel (64/36) rod as the anode and surroundedby a nickel foam as the cathode, were added DMF (50 mL), tetrabutylammonium bromide (1.2 mmol, 400mg), and 1,2-dibromoethane (2.5 mmol, 215 muL). The mixture was electrolyzed under argon at a constantcurrent intensity of 0.2 A at room temperature for 15 min. The current was then stopped, and the NiBr2bpycomplex (0.4 mmol, 150 mg), 3-amino- or 3-alkoxy/aryloxy-6-chloropyridazine (4 mmol), and aromatic orheteroaromatic halides (8 mmol) were sequentially added. The solution was electrolyzed at 0.2 A at roomtemperature until one of the starting materials was totally consumed. A saturated aqueous solution of EDTAsodium salt (100 mL) was added to the mixture, and the solution was extracted with dichloromethanecontaining 2-5% methanol (3 ¡Á 100 mL). The combined organic layers were dried over MgSO4, filtered,and evaporated under vacuum. The crude product was purified by flash chromatography on silica, elutedwith a gradient of solvents (pentane/acetone). For some polar cross-coupling compounds, a mixture ofacetone/methanol (95/5) was necessary.

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 24398-88-7.

Reference:
Article; Sengmany, Stephane; Sitter, Mathilde; Leonel, Eric; Le Gall, Erwan; Loirand, Gervaise; Martens, Thierry; Dubreuil, Didier; Dilasser, Florian; Rousselle, Morgane; Sauzeau, Vincent; Lebreton, Jacques; Pipelier, Muriel; Le Guevel, Remy; Bioorganic and Medicinal Chemistry Letters; vol. 29; 5; (2019); p. 755 – 760;,
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The chemical industry reduces the impact on the environment during synthesis 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate, I believe this compound will play a more active role in future production and life. 139102-34-4

Preparation of Example 389; Step i:; To methyl-4-bromo-2-methoxybenzoate (Aldrich) (1.0 g, 4.1 mmol) in THF(10 ml_), was added LiBH4 (0.13 g, 6.1 mmol). Ethanol (2 mL) was added dropwise. The resulting reaction mixture was stirred at room temperature for 20 h. 1 N NaOH was added, and the mixture was extracted with EtOAc. The organic layers were combined and washed with water and brine, then dried (MgSO4), filtered, and concentrated in vacuoXo provide the corresponfing benzyl alcohol (0.86 g, 4.0 mmol).

The chemical industry reduces the impact on the environment during synthesis 139102-34-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; WO2006/60461; (2006); A1;,
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4131-74-2, 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 4131-74-2 as follows.

26.16g (0.1411 mol) of octadecylamine was added to a 250 ml reaction flask, followed by addition of 100ml of high-boiling petroleum ether (90-120 C) or toluene or ethanol, 1-10% (molar ratio) of p-toluenesulfonic acid or hydrochloric acid or acetic acid or hydrochloric acid and 10g (0.04848 mol) of intermediate of product V. Placed in a constant temperature oil bath pot and stirred the reaction temperature was set at 125 , nitrogen protection plus condensate trap. (Time to complete the reaction time is about 36-48 hours, with increasing temperature the reaction flask to dissolve the solid into a liquid, when the end of the reaction, the flask was cooled to room temperature, the liquid into a solid whole. To the reaction flask with stirring adding an appropriate amount of methanol, and then subjected to suction filtration, washed with methanol 2-4 times, after heating to 40 degrees Celsius drained and dried under vacuum to give a white solid, yield 86-97%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4131-74-2, and friends who are interested can also refer to it.

Reference:
Patent; Shaoxing Ruikang Biotechnologies Co., Inc.; Mao, Lijuan; Liu, Shubai; Wang, Songping; Zhang, Zaixian; Wan, Dingfei; Peng, Chuanyang; Ding, Yifan; Sun, Xing; (21 pag.)CN105693545; (2016); A;,
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A common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, molecular formula is C11H20O4, 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. 541-16-2.

To a suspension of benzyltriethylamrnonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NaOH solution (92.4 g in 185 mL H2O) was added 1,2-dibromobutane (30.0 g, 138.9 mmol) and di-tert-butylmalonate (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred 18 h at rt, a mixture of ice and water was then added. The crude product was extracted with CH2Cl2 (3¡Á) and sequentially washed with water (3¡Á), brine and the organic extracts combined. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was flash chromatographed (100 g SiO2, 3% Et2O in hexane) to afford the titled product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

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

Reference:
Patent; Tu, Yong; Scola, Paul Michael; Good, Andrew Charles; Campbell, Jeffrey Allen; US2005/143316; (2005); A1;,
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252881-74-6, Adding some certain compound to certain chemical reactions, such as: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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 252881-74-6.

A solution of 2-14 (280 mg, 1.01 mmol), tert-butyl 3-(2-(2-(2-aminoethoxy)ethoxy) ethoxy)propanoate (2-15 where n=3, 337 mg, 1.22 mmol) and DIEA (0.7 mL, 4.04 mmol) in DMF (5 mL) was stirred at 80 C for overnight. The resulting mixture was diluted with EtOAc and washed with water five times. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (DCM/EtOAc = 90 : 10 to 50 : 50) to afford 2-16 where n =3.

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 252881-74-6.

Reference:
Patent; DANA FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael; JANG, Jaebong; DE CLERCQ, Dries; ECK, Michael; (201 pag.)WO2017/185036; (2017); 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 40546-94-9 as follows. 40546-94-9

A reaction mixture of 0.75 kg 3,4-dihydro-6-methyl -4-phenyl-2H-benzopyran-2-one, 0.262 kg sodium hydroxide and 0.93 L DM water was stirred at 60-650C for 2 hrs. The reaction was cooled to RT. 0.825 kg dimethylsulphate was added drop wise to reaction mixture within 1 hr. After the completion of addition, reaction mixture was stirred at same temperature for 2 hrs. Again solution of 0.186 kg sodium hydroxide in 0.93 L DM water was added at RT within 1 hr. The reaction mixture was stirred at 800C for 4 hrs. After completion of reaction, reaction was cooled to RT. 0.3 L Cone, hydrochloric acid was added drop wise to the reaction mixture till washing is neutral. The reaction mixture was stirred for 2 hrs, then filtered & washed with 2.0 L DM water to obtain wet cake. The wet cake was dried at 60-650C for 10-12 hrs to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid (Yield: 0.71 kg, 83%).[159] HPLC Purity: > 95 %.

According to the analysis of related databases, 40546-94-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALEMBIC LIMITED; PONNAIAH, Ravi; DESAI, Sanjay; SHAH, Chankrakant Chunilal; PATEL, Kalpesh Shantibhai; PAREKH, Viral Maheshbhai; WO2010/46801; (2010); A2;,
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Some common heterocyclic compound, 889858-12-2, name is tert-Butyl 4-bromo-2-fluorobenzoate, molecular formula is C11H12BrFO2, 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. 889858-12-2

To a 50 mL round-bottom flask was added Cs2CO3 (480 mg, 1.47 mmol, 3.00 equiv.), toluene (4 mL), tert-butyl 4-bromo-2-fluorobenzoate (162 mg, 0.59 mmol, 1.20 equiv.), 5-[[4- cyclopropyl-l-(2,6-dichlorophenyl)-1H-pyrazol-5-yl]methoxy]-3-ethyl-2- azabicyclo[2.2.1]heptane trifluoro acid acid salt 16b (200 mg, 0.49 mmol, 1.00 equiv.), Ruphos (82.3 mg, 0.20 equiv.), and Rupos preacatalyst (46 mg, 0.20 equiv.). The resulting mixture was heated at 110¡ãC overnight. After cooling to room temperature, the mixture was diluted with H2O (50 mL), extracted with ethyl acetate (100 mL x 2), and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/hexane (1/3) to afford tert-butyl 4-(5-[[4-cyclopropyl-l-(2,6-dichlorophenyl)-1H-pyrazol-5- yl]methoxy]-3-ethyl-2-azabicyclo[2.2.1]heptan-2-yl)-2-fluorobenzoate 18a(180 mg, 61percent) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 889858-12-2, its application will become more common.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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653-92-9, 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. 653-92-9 name is Methyl 2-bromo-4-fluorobenzoate, 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.

Into a 250-mL round-bottom flask, was placed a solution of Example 1-i, i.e, 1- [[2-(4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i -ylj methyljpiperazine (15.09 g, 47.32 mmol, 1.00 equiv) in DMA (150 mL), DIEA (12.9 g, 99.81 mmol, 2.00 equiv), methyl 2-bromo-4-fluorobenzoate (11.6 g, 49.78 mmol, 1.00 equiv). The resulting solution was stirred for 12 h at 100 degree. The reaction mixture was cooled to room temperature. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3xiOO mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3xiOO mL of brine. The mixture was dried over anhydrous sodium sulfate, then filtered and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:1-1:5). This resulted in 7 g (crude) of methyl 2-bromo-4-(4-[[2- (4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i -ylj methyljpiperazin- 1 -yl)benzoate as yellow oil. LC-MS: (ES, m/z): M+i=533, 531.

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

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); 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 619-42-1 as follows. 619-42-1

Synthesis methyl 4-(phenylamino)benzoate (Compound 17) Under argon atmosphere, a solution of methyl 4-bromobenzoate (3.5 g, 16.28 mmol), aniline (1.819 g, 19.53 mmol), palladium (II) acetate (218 mg, 0.97 mmol), rac-BINAP (506 mg, 0.81 mmol), and potassium carbonate (6.72 g, 48.62 mmol) in toluene (ca. 10 mL) was tightly capped in a 25 mL microwave vessel. The mixture was subjected to microwave irradiation at 160 C. for 2 h and then cooled to room temperature. The reaction mixture was diluted with DCM and filtered. The organic solvents were evaporated in vacuo, and the residue was suspended in methyl tert-butyl ether (150 mL). The organic phase was washed with saturated aqueous sodium bicarbonate, brine, dried (MgSO4), filtered and evaporated in vacuo. The obtained residue was purified by column chromatography (5% EtOAc in heptane to 60% EtOAc in heptane) to afford title compound 6 (3.55 g, 96% yield) as a pale green solid: mp 121-122 C.

According to the analysis of related databases, 619-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Diaz, Philippe; Diaz, Fanny; Petrov, Ravil Rashitovich; US2012/39804; (2012); A1;,
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