Month: March 2021

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. 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H13NO2

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3¡Á20 mL). The combined organic layers were washed with brine (2 ¡Á 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH¡¤H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white 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 35418-07-6.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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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. 16017-69-9, name is Ethyl 4-amino-2-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 4-amino-2-chlorobenzoate

To a solution of compound 3 (3.02g, 15.1mmol, 1equiv) in anhydrous ethanol (150mL) at 0C were added silver sulfate (4.68g, 15.1mmol) and iodine (3.81g, 15.1mmol). The solution was stirred for 45minat 0C and additional 90minat room temperature. After completion, a saturated aqueous sodium thiosulfate solution was added. The reaction mixture was filtered through Celite, washed with ethanol and filtrate was concentrated to dryness. Water was added and the product was extracted with EtOAc, the combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was triturated with cyclohexane and pentane yielding the compound 4 (3.18g, 9.77mmol, 65%) as a brown powder. Rf=0.3 (EtOAc/cyclohexane 1:9). Mp 125-127C; IR (ATR): 3470-3325, 1702, 1573, 1242cm-1; 1H NMR (400MHz, DMSO-d6): 1.27 (3H, t, J=6.8Hz), 4.21 (2H, q, J=6.8Hz), 6.23 (2H, br s), 6.78 (1H, s), 8.08 (1H, s); 13C NMR (100MHz, DMSO-d6): 14.1 (CH3), 60.4 (CH2), 122.9, 142.2 (CHarom), 114.3, 116.5, 134.3, 153.1 (Carom), 163.0 (CO); HRMS (ESI+) calcd for C9H10ClINO2 (M+H)+ 325.9445, found 325.9443

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 16017-69-9.

Reference:
Article; Esvan, Yannick J.; Zeinyeh, Wael; Boibessot, Thibaut; Nauton, Lionel; Thery, Vincent; Knapp, Stefan; Chaikuad, Apirat; Loaec, Nadege; Meijer, Laurent; Anizon, Fabrice; Giraud, Francis; Moreau, Pascale; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 170 – 177;,
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Electric Literature of 35598-05-1,Some common heterocyclic compound, 35598-05-1, name is Methyl 4-methoxy-2-methylbenzoate, molecular formula is C10H12O3, 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.

[0180] 4-Fluoro-2-methyl-benzoic acid methyl ester (600 mg, 3.6 mmol), N-bromosuccinimide (635 mg, 3.6 mmol) and benzoyl peroxide (43 mg, 1.79 mmol) in CCU (15 mL) was stirred at 90 C for 3 hours. The reaction was cooled to room temperature, filtered, washed with CCI4 and the solvent was removed under reduced pressure to provide a white solid. .H NMR (300 MHz, CDCI3): 5 8.01 (d, 1H), 6.99 (d, 1H), 6.88 (dd, 1H), 4.98 (s, 2H), 3.93 (s, 3H), 3.89 (s, 3H). [0181] The following compounds were made in a similar fashion:

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-methoxy-2-methylbenzoate, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); 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. 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Diethyl 1,1-cyclopropanedicarboxylate

To a stirred solution of diethyl cyclopropane-1, 1-dicarboxylate (2.13 g, 11.4 mmol) in THF (80 mL) at RT, lithium aluminum tri-tert-butoxyhydride (38.76 mL, 38.76 mmol, 1.0 M solution in THF) was added slowly. After the addition was completed, the reaction mixture was stirred at RT for 18 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with IN aq HCI (20 mL), water (20 mL), 5% aq. NaHC03 (25 mL), brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated to afford the title compound (1.3 g, 79%, yellow oil). *H NMR (400 MHz, CDCI3) : delta = 4.20- 4.13(m, 2H), 3.62 (m, 2H), 2.61 (m, 1H), 1.29-1.24 (m, 5H), 0.88-0.85 (m, 2H) ppm.

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 1559-02-0.

Reference:
Patent; LEO PHARMA A/S; NIELSEN, Simon Feldbaek; LARSEN, Jens Christian H¡ãjland; WO2013/92739; (2013); 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 721-63-1 as follows. SDS of cas: 721-63-1

A 100 mL two-necked reaction flask was placed in an ice bath at 0 C, p-trifluoromethylphenylacetate 2i (10.0 mmol) and 20 mL of acetonitrile were added, and p-toluenesulfonyl azide 3a (11.0 mmol) was added.1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (15.0 mmol) was slowly added.Stir for 5 minutes in an ice bath and place in a microwave reactor.Set power 400W, heating temperature 40 C, heating time 60 min,Turn on the exhaust fan.After the reaction is completed, the mixture is cooled to room temperature, quenched by the addition of ammonium chloride solution, and extracted with dichloromethane and water. The organic phase is collected, dried over anhydrous sodium sulfate, filtered, and evaporated. Chromatography (eluent is petroleum ether (60-90 C) / ethyl acetate, v / v = 80:1),The red solid target product 1i (2.06 g, yield 80%) was obtained.The target product was confirmed by nuclear magnetic resonance spectroscopy and high resolution mass spectrometry.

According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Tech University; Gao Zhen; Yi Xiangyan; Huang Fei; Huang He; Yu Yang; Zhang Zhipeng; Xue Lian; Wang Lize; Qiao Nasen; (12 pag.)CN108727216; (2018); A;,
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Reference of 15963-46-9, 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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

5-(2,4-dichlorophenyl)-1,3,4-oxadiazole-2-thiol (0.1 g, 0.41 mmol), cesium carbonate (0.17 g, 0.51 mmol), and sodium iodide (0.006 g, 0.04 mmol) were dissolved in 2 mL DMSO. Methyl 3-chlorocyclobutanecarboxylate (0.09 g, 0.61 mmol, 0.08 mL) was added and the mixture was stirred at 100 C. for 40 hr. The reaction was diluted with EtOAc and H2O, and product was extracted with EtOAc (3*15 mL). The organic layers were combined, washed with brine (2*15 mL), and evaporated in vacuo. The oil was subjected to silica gel chromatography eluting with 15% EtOAc: 75% Hex. The diastereomers were separated and fractions containing products were concentrated. Trans: 1H NMR (500 MHz, CDCl3-d) delta ppm 7.91 (d, J=8.5 Hz, 1H) 7.57 (d, J=2.0 Hz, 1H) 7.39 (dd, J=8.5, 2.0 Hz, 1H) 4.48-4.38 (m, 1H) 3.73 (s, 3H) 3.40 (tt, J=10.4, 5.7 Hz, 1H) 2.94 (tt, J=8.4, 5.8 Hz, 2H) 2.56 (dtd, J=13.3, 6.4, 2.4 Hz, 2H); 13C NMR (500 MHz, CDCl3-d) delta ppm 174.87, 164.01, 163.34, 138.08, 133.74, 131.58, 131.19, 127.61, 121.39, 52.07, 37.62, 35.22, 32.73; TOF ES+ MS: (M+H) 359.0; HPLC Ret: 8.02 min. cis: 1H NMR (500 MHz, CDCl3-d) delta ppm 7.90 (d, J=8.5 Hz, 1H) 7.57 (d, J=2.0 Hz, 1H) 7.39 (dd, J=8.5, 2.0 Hz, 1H) 4.30 (p, J=8.6 Hz, 1H) 3.71 (s, 3H) 3.17 (p=8.9 Hz, 1H) 2.95-2.85 (m, 2H) 2.55 (qd, J=9.7, 2.9 Hz, 2H); 13C NMR (500 MHz, CDCl3-d) delta ppm 173.80, 164.17, 163.30, 138.03, 133.72, 131.57, 131.16, 127.59, 121.39, 52.02, 35.45, 34.45, 33.77; TOF ES+ MS: (M+H) 359.0; HPLC Ret: 7.89 min.

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; Larsen, Scott D.; Neubig, Richard; Hutchings, Kim; Kahl, Dylan; Lisabeth, Erika Mathes; (56 pag.)US2019/308947; (2019); A1;,
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Synthetic Route of 41841-16-1, 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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 4-bromophenylacetate (0.9 g, 4.5 mmol) was dissolved in chloroform (30 mL).Add NBS (0.3g, 4.5mmol),Stir at 70 C for 2 hours.After the reaction solution is diluted, it is washed with water.The mixture was washed with saturated brine, dried over anhydrous sodium sulfate and evaporated.Purified by silica gel column chromatography,A colorless liquid (0.5 g, 38%) was obtained.

The synthetic route of Methyl 2-(4-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Xiangjin Biological Technology Co., Ltd.; Sun Fang; Zhan Youni; (53 pag.)CN108341814; (2018); A;,
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Electric Literature of 40872-87-5, 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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

The chemical industry reduces the impact on the environment during synthesis Methyl 3-amino-4-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 106685-41-0, name is Methyl 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate, 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 106685-41-0, HPLC of Formula: C29H30O3

Example 8; Preparation of Potassium salt of 6-[3-(l-adamantyl)-4-methoxy phenyl]-2 -naphthoic acid(VI):- To a solution of Methyl ester of 6-[3-(l-adamantyl)-4-methoxy phenyl] -2 naphthoic acid(25 g, 58 mmol) in 1,4-Dioxane ( 300ml) was stirred at refluxed temperature. Then potassium hydroxide (10 g, 175 mmol) in water (50 ml) was added slowly added into the reaction mixture. The reaction mixture was heated at 900C for 5 h. Then tetrahydrofuran(300 ml) was added slowly and again mixture was heated at 900C for 1 hr. The reaction mixture was cooled, solid separated, filtered and dried.[Yield: 24 g, 94 %]

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 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; USV LIMITED; WO2007/125542; (2007); A2;,
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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 73792-08-2 as follows. Formula: C8H8FNO2

Svnthesis 66Step (i): Methyl 4-(3,5-diisopropoxy-4-ethoxybenzamido)-2-fluorobenzoate1A mixture of 3,5-diisopropoxy-4-ethoxybenzoic acid (1) (300 mg, 1.06 mmol), methyl 4- amino-2-fluorobenzoate (2) (189 mg, 1.12 mmol) and TEA (149 muIota_, 1.06 mmol) in EtOAc (2.5 mL) was treated with T3P (50% wt. in EtOAc, 1.69 mL, 2.66 mmol). The reaction mixture was stirred at 60C for 1 h, and then allowed to cool to RT. The mixture was diluted with DCM (5 mL) and washed sequentially with 1 M HCI (5 mL) and satd. NaHC03 (5 mL). The solvent was removed in vacuo and the residue was purified by silica gel chromatography (12 g, 0-30% EtOAc in isohexane) to afford methyl 4-(3,5-diisopropoxy- 4-ethoxybenzamido)-2-fluorobenzoate (3) (326 mg, 56%): m/z 434 [M+H]+ (ES+), 432 [M- H]- (ES-). H-NMR (400 MHz, DMSO-cf6) delta: 7.93 (1 H, t), 7.82 (1 H, br s), 7.73 (1 H, dd),7.27 (1 H, dd), 7.04 (2H, s), 4.60 (2H, sep), 4.09 (2H, q), 3.91 (3H, s), 1.39-1.34 (15H, m).

According to the analysis of related databases, 73792-08-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KING’S COLLEGE LONDON; CORCORAN, Jonathan Patrick Thomas; KALINDJIAN, Sarkis Barret; BORTHWICK, Alan David; ADAMS, David Reginald; BROWN, Jane Theresa; TADDEI, David Michel Adrien; SHIERS, Jason, John; WO2011/27106; (2011); A1;,
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