Tag: M.W=200-300

Electric Literature of 35120-18-4, A common heterocyclic compound, 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, molecular formula is C7H11BrO2, 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 6-methoxyquinoline-4-thiol 4b (477 mg, 2.5 mmol), ethyl 1-bromo cyclobutanecarboxylate (620 mg, 2.9 mmol) and cesium carbonate (326 mg, 7.5 mmol) Was added to 10 mL of N, N-dimethylformamide. The reaction solution was heated to 60 DEG C and stirred for 2 hours. 50 ml of water was added to the reaction solution, and the mixture was extracted with ethyl acetate (50 ml x 4). The organic phases were combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound ethyl 1 – ((6-methoxyquinolin-4-yl) thio) cyclobutanecarboxylate 4c (620 mg, brown oil), yield: 78%.

The synthetic route of 35120-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd; Jiangsu Hengrui Medicine Co.,Ltd.; Peng, Jian Biao; Sun, Pia Ohyang; Lan, Jiong; Koo, Cheon Yang; Lee, Siaotao; Liu, Bonnian; Han, Quanzhou; Hoo, Kwiye; Jean, Pang Pang; Dong, Qing; Cao, Guo Qing; (67 pag.)KR2016/6207; (2016); A;,
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Electric Literature of 541-16-2, 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.

General procedure: A mixture of 2-(3, 4-dichlorophenyl)acetonitrile (5 mmol), ditert-butyl malonate (3 mmol), and Fe(ClO4)3·H2O (5 mol%) wasplaced in a round-bottomed flask. Then, the reaction mixturewas heated at 80 C for 5 h. After completion of the reactionmonitored by thin layer chromatography (TLC), water (10 mL)was added and the reaction mixture was extracted with ethylacetate (3 × 20 mL). The organic layers were collected, combined,washed with water (3 × 20 ml), dried over anhydrousNa2SO4, and concentrated under vacuum. The pure product wasobtained by directly passing through a silica gel (200-300mesh) column to give a white powder 1m (1.08 g, 84% yield).Compound 1m1H NMR (400 MHz, CDCl3): delta = 7.41-7.35 (m, 2 H), 7.12-7.10 (m,1 H), 5.31 (s, 1 H), 3.40 (s, 2 H), 1.32 (s, 9 H) ppm. 13C NMR (100MHz, CDCl3): delta = 168.9, 135.6, 132.7, 131.2, 131.2, 130.6, 128.6,51.6, 43.5, 28.7 ppm. HRMS: m/z calcd for C12H15Cl2NO [M + H]+:259.0531; found: 259.0533.

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:
Article; Feng, Chengliang; Yan, Bin; Yin, Guibo; Chen, Junqing; Ji, Min; Synlett; vol. 29; 17; (2018); p. 2257 – 2264;,
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Reference of 27007-53-0, These common heterocyclic compound, 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, 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.

Step 2. methyl 5-chloro-2-cyanobenzoate To a stirred solution of methyl 2-bromo-5-chlorobenzoate (11.5 g, 46 mmol) in degassed DMF (50 mL) was added zinc cyanide (2.82 g, 24.0 mmol) and palladium tetrakis-triphenylphosphine (1.0 g, 0.86 mmol) and the mixture was heated to 90 C. for 18 h. The reaction was partitioned between EtOAc (200 mL) and water (100 mL). The organic phase was concentrated in vacuo and the residue was purified by flash chromatography eluding with a gradient of 10%, 15%, 20% ethyl acetate in hexane yielding methyl 5-chloro-2-cyanobenzoate as a white solid (8.0 g, 88% yield). TLC Rf=0.4 (15% EtOAc-hexanes); HPLC RT=3.13 min (Method A); 1H NMR (CDCl3, 400 MHz) 8.13 ppm (d, 1H, J=1.83 Hz); 8.09 ppm (d, 1H, J=8.24 Hz); 7.29 ppm (dd, 1H, J=8.34, 2.10 Hz); 4.02 ppm (s, 3H). Step. 3 2-aminomethyl-5-chlorobenzyl Alcohol

The synthetic route of 27007-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Williams, Peter D.; Lyle, Terry A.; Morrissette, Matthew M.; Tran, Lekhanh O.; Staas, Donnette D.; US2003/13700; (2003); A1;,
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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. 206548-14-3, name is Methyl 2-amino-5-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H10BrNO2

Example 134 5-Bromo-2-(4-methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl ester To a stirred solution of 24.5 g (100 mmol) of the product of Example 133 in 100mL of pyridine was added 21.0 g (100mmol) of p-methoxybenzenesulfonyl chloride and the resulting mixture was heated to 80 C for 24 h. The reaction mixture was then quenched with ice cold water and acidified with concentrated HCl. The resulting mixture was extracted with chloroform, washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with diethyl ether, filtered and dried to provide 35g (84%) of the desired product as a brown solid. Electrospray Mass Spec 416, (M+H).

According to the analysis of related databases, 206548-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; EP938471; (2001); B1;,
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Synthetic Route of 35120-18-4,Some common heterocyclic compound, 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, molecular formula is C7H11BrO2, 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 (5Z,8Z,1 1 Z,14Z,17Z)-icosa-5,8,1 1 ,14,17-pentaene-1 -thiol (305 mg, 1 .00 mmol) in dry DMF (10 mL) at 0C under inert atmosphere was added NaH (60% in mineral oil, 44 mg, 1 .1 mmol). After fifteen minutes ethyl 2-bromo-cyclobutane carboxylate (170 muIota_, 1 .05 mmol) was added and the mixture was stirred for 1 .5 hour at 0C. The reaction was quenched by addition of sat. aq. NH4CI (20 mL). Heptane (50 mL) was added, and the phases were separated. The water phase was extracted with heptane (2×25 mL). The combined organics were washed with water (25 mL) and brine (25 mL), dried (MgSC ), filtered and evaporated to give 409 mg of the title compound as a crude oil. Purification by flash chromatography on silica gel using isocratic elution (heptane:acetone 98:2) afforded 243 mg (56% yield) of the title compound as oil. 1 H- NMR (300 MHz, CDCI3): delta 0.95 (t, 3H), 1.27 (t, 3H), 1 .42 (d, 3H), 1.54 (m, 2H), 1.84 (m, 1 H), 1 .96-2.23 (m, 7H), 2.51 (m, 2H), 2.60 (m, 2H), 2.73-2.90 (m, 8H), 4.18 (m, 2H), 5.23-5.43 (m, 10H); MS (CI (CH4)): 471 [M+C3H5]+, 459 [M+C2H5]+, 431 [M+H]+, 385 [M-OEt]+, 357 [M-C02Et]+, 303 [R-S],+.

The synthetic route of 35120-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRONOVA BIOPHARMA NORGE AS; STEINEGER, Hilde; (38 pag.)WO2016/173923; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35065-86-2, name is 3-Bromophenyl acetate, 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 35065-86-2, Safety of 3-Bromophenyl acetate

In a 250 mL round bottom flask (8) (5.49 g, 26 mmol) and anhydrous AlCl3 (6.92 g, 51 mmol) was mixed thoroughly on oil bath at 160 C for 2 h. Reaction mixture was poured into ice water and concentrated hydrochloric acid solution was added to break complex formed during reaction. The mixture was taken in AcOEt (50 mL * 3). The organic layer was combined and washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 30:1) gave (9) (3.85 g, 70 %) as white solid. Mp: 36-38 C, MS (EI) [M]+: m/z = 213, 1H NMR (400 MHz, CDCl3) delta ppm: 7.60 (d, J = 8.0 Hz, 1H), 7.20 (s, 1H), 7.07 (d, J = 8.0 Hz, 1H), 2.63 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromophenyl acetate, and friends who are interested can also refer to it.

Reference:
Article; Wang, Chen; Gao, Hongping; Dong, Jinyun; Zhang, Yanmin; Su, Ping; Shi, Yaling; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 277 – 284;,
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Electric Literature of 104670-74-8, The chemical industry reduces the impact on the environment during synthesis 104670-74-8, name is Methyl 2-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

Example 83: Synthesis of 2-amino-3-[2-(3- hydroxyphenyl)ethynyl]benzoic acid 2-amino-3-[2-(3-hydroxyphenyl)ethynyl]benzoic acid: To a sealed tube was loaded a mixture of 2-amino-3-bromo-benzoic acid methyl ester (50 mg, 0.22 mmol), Pd(PPh3)2Cl2 (15.4 mg, 0.022 mmol) and Cul (4.2 mg, 0.022 mmol) in triethyl amine (1 mL). The mixture was degassed with N2 for 10 minutes, 3- ethynyl-phenol (103 mg, 0.87 mmol) was added and the mixture degassed with N2 for 5 minutes. The reaction mixture was heated at 90 C for 5 hours. After cooling to ambient temperature, the crude mixture was filtered through celite and washed with dichloromethane. The filtrate was concentrated and purified by preparative thin layer chromatography eluting with ethyl acetate/hexane (30%) to give a solid intermediate. To the solid intermediate in tetrahydrofuran/methanol (1 mL/0.2 mL) was added sodium hydroxide solution (2 N in water, 0.2 mL, 0.4 mmol) and the solution was stirred at room temperature for 18 hours. 1 N hydrochloric acid aqueous solution was added dropwise until pH = 1 and the reaction mixture was purified through preparative HPLC to give 11 mg (14% for 2 steps) of the pure product as a white solid. LCMS (ESI) mlz 254.1 (M+l)+.

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-amino-3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE WISAR INSTITUTE OF ANATOMY AND BIOLOGY; MESSICK, Troy, E.; SMITH, Garry, R.; REITZ, Allen, B.; LIEBERMAN, Paul, M.; WO2015/73864; (2015); A1;,
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Reference of 2557-13-3, A common heterocyclic compound, 2557-13-3, name is Methyl 3-(trifluoromethyl)benzoate, molecular formula is C9H7F3O2, 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.

Sodium hydride (60% dispersion in oil, 390 mg, 9.75 mmol) was first washed with hexanes to remove the oil and was then suspended in 7 ml dimethylformamide. A solution of methyl 3-(trifluoromethyl)benzoate 29 (1.0 g, 4.9 mmol) in 2 ml dimethylformamide was added drop-wise and with stirring. Upon addition, the mixture was stirred for 1 h at room temperature. Acetone (400 ml, 5.44 mmol) was added drop-wise and the mixture was stirred overnight at room temperature. The mixture was poured into water and the aqueous layer was extracted four times with ether. The aqueous layer was acidified with 2 N hydrochloric acid and was extracted three times with ether. The combined organics were dried over sodium sulphate and evaporated under reduced pressure. The residue was purified using the SP1 Purification System (ethyl acetate-hexane gradient, 0:100 rising to 10:90) to give 30 (640 mg, 2.78 mmol, 56%) as an oil. Purity 100%.

The synthetic route of 2557-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Andres, Miriam; Bravo, Monica; Buil, Maria Antonia; Calbet, Marta; Castillo, Marcos; Castro, Jordi; Eichhorn, Peter; Ferrer, Manel; Lehner, Martin D.; Moreno, Imma; Roberts, Richard S.; Sevilla, Sara; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 168 – 184;,
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Synthetic Route of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, 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.

A mixture of methyl 4-bromo-3-methylbenzoate (20.0 g, 87.3 mmol), 2- (trifluoromethyl)benzeneboronic acid (24.9 g, 131.0 mmol), potassium carbonate (24.1 g, 174.6 mmol) and bis(tricyclohexylphosphine)palladium (II) dichloride (64.5 mg, 0.09 mmol) was prepared in dioxane (200 ml.) and water (50 ml.) under N2 atmosphere. The mixture was heated at 1000C for 3 hours. A 5N aqueous solution of NaOH (100 ml.) was added and the reaction mixture was stirred at 1000C for one additional hour. The reaction mixture was cooled at RT and the aqueous layer was removed. The organic layer was filtered through a Celite pad, concentrated until 75 ml under reduced pressure, diluted with water (125 ml) and washed with MTBE (2×200 ml_). The aqueous layer was acidified with a 5N aqueous solution of HCI (25 ml, pH~1 ) and extracted with MTBE (2×100 ml). The organic layers were combined, dried (Na2SO4) and filtered through a Celite pad. The solution was concentrated until 100 ml_, then heptane was added (200 ml_). The mixture was concentrated until 100 ml_. The precipitate was filtered off and rinsed twice with heptane, then dried under reduced pressure to give the title compound as a white powder (22.5 g, 92%). HPLC (Method A), Rt: 4.4 min (purity: 100%). UPLC/MS, M-(ESI): 279.0. 1H NMR (DMSO-d6, 300 MHz) delta 13.00 (s, 1 H), 7.87 (m, 2H), 7.80 (dd, J=7.9, 1.6 Hz, 1 H), 7.75 (m, 1 H), 7.64 (m, 1 H), 7.34 (d, J=7.6 Hz, 1 H), 7.23 (d, J=7.9 Hz, 1 H), 2.02 (s, 3H).

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 SERONO S.A.; QUATTROPANI, Anna; GERBER, Patrick; DORBAIS, Jerome; WO2010/100142; (2010); A1;,
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Application of 24807-40-7, 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. 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

An aqueous solution of NaOH (1 M, 270 mL) was added to a mixture of the 3-(4-benzyloxyphenyl)propionic acid methyl ester from Step 2 above in MeOH (600 mL) and the reaction was stirred overnight. The crystalline ppt was collected by filtration, air dried and then partitioned between EtOAc/Et2O/1 M HCl (500 mL, 250 mL, 150 mL). The organic phases were dried over MgSO4 and evaporated to give the product as a white solid (16.2 g, 70%, 3 Steps). 1H NMR (CDCl3) delta 2.61-2.68 (m, 2H), 2.86-2.93 (m, 2H), 5.03 (s, 2H), 6.88-6.93 (m, 2H), 7.10-7.15 (m, 2H), 7.28-7.45 (m, 5H).

The synthetic route of Methyl 3-(4-(benzyloxy)phenyl)propanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US2005/176701; (2005); A1;,
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