Month: February 2021

Reference of 73792-08-2,Some common heterocyclic compound, 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, molecular formula is C8H8FNO2, 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.

[00471] Under an atmosphere of argon acetyl chloride (2.0 mL, 31 mmol) in dichloromethane (5 mL) was added dropwise to a stirred solution of 59 (2.0 g, 12 mmol) and Hunig’s base (8 mL, 48 mmol)) in dichloromethane (50 mL) at -10 C. The reaction was stirred for 1 hour then quenched with saturated sodium bicarbonate solution (50 mL). The mixture was extracted with dichloromethane (3 x 30 mL) and combined extracts dried with sodium sulfate. The mixture was concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-100% ethyl acetate in hexane) provided 60 (2.07 g, 83%) as a solid: LRESIMS m/z 212.0 [M+H]+, calcd. for C10H11F1N1O3 212.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-2-fluorobenzoate, its application will become more common.

Reference:
Patent; CALCIMEDICA, INC.; ROGERS, Evan; CAO, Jianguo; WANG, Zhijun; GREY, Jonathan; WHITTEN, Jeffrey, P.; WO2014/43715; (2014); 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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 653-92-9

To a mixture of methyl 2-bromo-4-fluorobenzoate (10.1 g, 43.34 mmol, 1.00 equiv) in THF (100 ml) with Cs2C03 (42 g, 128.91 mmol, 3.00 equiv) and Pd(dppf)CI2 (3.5 g, 4.78 mmol, 0.1 1 equiv) was added Et3B (1 M in tetrahydrofuran) (65 ml, 65 mmol, 1.50 equiv). The reaction mixture was stirred overnight at 80C. Water was added and the mixture was extracted with EA thrice. The combined extracts were washed with water, saturated brine and dried over anhydrous Na2S04, then concentrated and purified by chromatography on silica gel (1 :30 EA/PE) to yield methyl 2-ethyl-4- fluorobenzoate as a yellow oil.

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; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
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Reference of 40872-87-5, These common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-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.

EXAMPLE 16: 4-Chloro-3-(cyclohexylaminocarbonylamino)benzoylguanidine hydrochloride was prepared from methyl 4-chloro-3-aminobenzoate and cyclohexyl isocyanate in accordance with variants 3 and 2 B. (Benzoic acid ester intermediate: colorless crystals, m.p. 158 C.) Colorless crystals, m.p. 223 C.

Statistics shows that Methyl 3-amino-4-chlorobenzoate is playing an increasingly important role. we look forward to future research findings about 40872-87-5.

Reference:
Patent; Hoechst Aktiengesellschaft; US5559153; (1996); A;,
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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. 5335-05-7, name is Chloromethyl benzoate, A new synthetic method of this compound is introduced below., Safety of Chloromethyl benzoate

b) Compound B59:To a solution of Compound B29 (1.06g, 3.19 mmol; Example 11 (c)) and silver carbonate (0.86 g, 3.19 mmol) in acetonitrile (25 mL) was added chloromethylbenzoate (2.73 mL, 16.0 mmol). The mixture was stirred for 4h at 600C and filtered over a pad of Celite. The cake was washed with acetonitrile (2x20ml). The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (hexanes/ethyl acetate 90:10 to 50:50). Compound B59 (1.30 g, 97% yield) was obtained as a colorless oil. 1H NMR (CDCI3, 500 MHz) delta in ppm 1.24 (s, 6H), 1.26 (t, J=7.0Hz, 3H), 2.39 (quint, J=7.5Hz, 2H), 3.30 (t, J=7.0Hz, 2H), 3.44 (t, J=7.5Hz, 2H), 4.15 (q, J=7.5Hz, 2H), 4.19 (s, 2H), 6.07 (s, 2H), 7.50 (t, J=7.5Hz, 2H), 7.65 (t, J=7.5Hz, 1 H), 8.09 (d, J=7.0Hz, 2H).

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; BELLUS HEALTH (INTERNATIONAL) LIMITED; KONG, Xianqi; LEVENS, Nigel; BOUZIDE, Abderrahim; CIBLAT, Stephane; FRENETTE, Richard; RENAUD, Johanne; WO2011/17800; (2011); 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 924-99-2 as follows. Recommanded Product: Ethyl 3-(dimethylamino)acrylate

General procedure: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

According to the analysis of related databases, 924-99-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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Reference of 496841-90-8,Some common heterocyclic compound, 496841-90-8, name is Ethyl 2-fluoro-5-methylbenzoate, molecular formula is C10H11FO2, 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.

Reference Example 11-2 Ethyl 5-(bromomethyl)-2-fluorobenzoate To a solution of ethyl 2-fluoro-5-methylbenzoate (243 mg) in carbon tetrachloride (6.7 mL), N-bromosuccinimide (261 mg) and 2,2′-azobis(isobutyronitrile) (22 mg) were added, and the mixture was stirred at an outer temperature of 65C for 2 hours. After the reaction solution was concentrated under reduced pressure, the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 49:1 to 17:3) to give the title compound (208 mg) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.36 – 1.46 (m, 3 H) 4.34 – 4.45 (m, 2 H) 4.48 (s, 2 H) 7.07 – 7.16 (m, 1 H) 7.48 – 7.58 (m, 1 H) 7.92 – 7.98 (m, 1 H). MS ESI/APCI Multi posi: 283[M+Na]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-fluoro-5-methylbenzoate, its application will become more common.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; TANAKA, Hiroaki; KAWAMURA, Madoka; HAMADA, Makoto; KOBASHI, Yohei; ITO, Yuji; SUZUKI, Kazuaki; BOHNO, Ayako; FUNAYAMA, Kosuke; (510 pag.)EP3666766; (2020); 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. 120974-97-2, name is (E)-Methyl 2-(methoxyimino)-2-(o-tolyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C11H13NO3

To the solution of IV (5 g, 24.0 mmol) in CCl4 (150 mL) was added NBS (4.7 g, 26.4 mmol) andBPO (1 g, 4.13 mmol). The reaction mixture was heated to reflux until the starting material had beencompletely consumed as judged by TLC. The precipitate was filtered off, and the solvent wasevaporated under reduced pressure. The residue was purified by a silica-gel column chromatography(petroleum ether/EtOAc = 15:1) to give (E)-methyl 2-(2-(bromomethyl)phenyl)-2-(methoxyimino)-acetate (V). Yield 85%; Yellow oil; 1H-NMR (CDCl3) delta 7.47-7.13 (m, 4H, Ar-H), 4.32 (s, 2H, CH2),4.04 (s, 3H, OCH3), 3.85 (s, 3H, OCH3). Anal. calcd for C11H12BrNO3: C 46.18, H 4.23, N 4.90; foundC 46.32, H 4.21, N 4.88.

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 120974-97-2.

Reference:
Article; Liu, Yuanyuan; Li, Yi; Chen, Nanqing; Lv, Kunzhi; Zhou, Chao; Xiong, Xiaohui; Li, Fangshi; Molecules; vol. 19; 6; (2014); p. 8140 – 8150;,
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Application of 2905-65-9, 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. 2905-65-9, name is Methyl 3-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Pd(OAc)2 or Pd2(dba)3/2-Catalyzed Amination of Aryl chlorides (Table 5).General Procedure: An oven-dried Schlenk flask equipped with a magnetic stirring bar was charged with Pd(OAc)2 or Pd2(dba)3 (x mol %, see Table 5) and NaO-t-Bu (1.5 mmol) or Cs2CO3 (1.5 mmol). Amine (1.2 mmol) and aryl chloride (1.0 mmol) were also added at this time if they were solids. The flask was capped with a rubber septum, evacuated and then flushed with argon. This cycle was repeated three times. Ligand 2 (2x mol %, see Table 5) was then added via syringe from a stock solution. Aryl chloride (if a liquid, 1.0 mmol), amine (if a liquid, 1.2 mmol) and toluene (3 mL) were then successively added by syringe. The reaction mixture was heated at 110 C. until the starting material had been completely consumed as judged by TLC (24 hours). The mixture was cooled to room temperature, adsorbed onto silica gel and then purified by column chromatography (hexanes/ethyl acetate as eluent).

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

Reference:
Patent; Iowa State University Research Foundation, Inc.; US7385058; (2008); B1;,
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16017-69-9, name is Ethyl 4-amino-2-chlorobenzoate, 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. SDS of cas: 16017-69-9

Stage 1: ethyl 4-amino-2-chloro-5-iodobenzoate An iodine solution in ethanol was admixed with silver(I) sulphate and ethyl 4-amino-2-chlorobenzoate and then stirred at room temperature for 45 min. The reaction mixture was filtered through a frit and the filtrate was concentrated under reduced pressure. The residue was slurried in EtOAc, and dilute sodium hydrogencarbonate solution was added. Once everything had gone into solution, the aqueous phase was removed and sodium thiosulphate was dissolved therein. The organic phase was washed again with the aqueous phase and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. Column chromatography purification on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 10% ethyl acetate to 33% ethyl acetate) gave 1.85 g (74% of theory) of ethyl 4-amino-2-chloro-5-iodobenzoate. HPLC-MS: logP=2.95; mass (m/z): 326.0 (M+H)+; 1H NMR (CD3CN) 1.32 (t, 3H), 4.27 (q, 2H), 5.01 (br. s, 2H), 6.80 (s, 1H), 8.16 (s, 1H).

The synthetic route of 16017-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Intellectual Property GmbH; Heil, Markus; Heilmann, Eike Kevin; Holmwood, Graham; Jeschke, Peter; Maue, Michael; Kapferer, Tobias; Reidrich, Matthias; Becker, Angela; Malsam, Olga; Losel, Peter; Voerste, Arnd; Goergens, Ulrich; Andree, Roland; US2014/88167; (2014); 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 764667-64-3 as follows. HPLC of Formula: C14H11F3O5

Under nitrogen protection,Acetonitrile (284 mL) was added to a 250 mL three-necked flask in sequence,Compound C (56.7 g, 0.179 mol) and benzyl alcohol (19.4 g, 0.179 mol),Stirring.Heating to reflux(The internal temperature of 80 ~ 84 for the normal boiling point)About 24 hours.Cooling to below 30 ,concentrate,3 V methanol was added,0 ~ 5 crystallization of 12h,Filtered product 47.2g,Yield 81.6%.

According to the analysis of related databases, 764667-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai SynCores Technologies, Inc.; Qian, Wangke; Hong, Jian; Wang, Yusheng; Wang, Boyu; Huang, Luning; Gu, Hong; (8 pag.)CN105566138; (2016); A;,
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