Category: esters-buliding-blocks

Electric Literature of 59247-47-1, A common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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: Under nitrogen atmosphere, a mixture of alcohol 1a (28.6 mg, 0.10 mmol, 1.0 equiv), 4-bromoanisole (37.4 mg, 0.20 mmol, 2.0 equiv), [C12H8NH2PdCl]2 (1.5 mg, 2.5 mol%), L10 (13.6 mg, 15 mol%) and NaH (7.2 mg, 0.30 mmol, 3.0 equiv) in anhydrous toluene (2.0 mL), were heated at 80C for 12 h. After being cooled to room temperature, the solvent was removed and the residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate = 30:1) to afford the desired product 2a (38.0 mg, 97%, 96% ee).

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Deng, Ruixian; Xi, Junwei; Li, Qigang; Gu, Zhenhua; Chem; vol. 5; 7; (2019); p. 1834 – 1846;,
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Application of 2905-67-1, 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. 2905-67-1, name is Methyl 3,5-dichlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 25 g of 3,5-dichlorobenzoic acid methyl and 22.5 g of trifluoromethyltrimethylsilane in 300 g of dimethoxyethane, 0.37 g of cesium fluoride was added with ice-cooling and the mixture was warmed to room temperature and stirred for 4 hours. After disappearance of the raw material was confirmed, 200 g of water was put into the reaction solution to extract with 200 g of ethyl acetate. After the organic layer was dehydrated and dried with saturated saline followed by anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 35.5 g of 1-(3,5-dichlorophenyl)-2,2,2-trifluoro-1-trimethylsilyloxy-1-methoxyethane as yellow liquid matter.

The chemical industry reduces the impact on the environment during synthesis Methyl 3,5-dichlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nissan Chemical Industries, Ltd.; EP1975149; (2008); A1;,
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Electric Literature of 383-62-0, The chemical industry reduces the impact on the environment during synthesis 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, I believe this compound will play a more active role in future production and life.

To a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.5 g, 2.58 mmol, 1 eq) in DMF (5 mL) was added ethyl 2-chloro-2,2-difluoro-acetate (490.20 mg, 3.09 mmol, 392.16 uL, 1.2 eq) and K2CO (712.26 mg, 5.15 mmol, 2 eq). The mixture was stirred at 60 C for 16 h. The reaction mixture was poured into H2O 10 mL, and extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine (10 mL x 2), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (0.3 g, crude) as yellow solid, which was used into the next step without further purification. The structure was confirmed by 1H NMR and HOSEY.

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, Ethyl 2-chloro-2,2-difluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MARINEAU, Jason, J.; ZAHLER, Robert; CIBLAT, Stephane; WINTER, Dana, K.; KABRO, Anzhelika; ROY, Stephanie; SCHMIDT, Darby; CHUAQUI, Claudio; MALOJCIC, Goran; PIRAS, Henri; WHITMORE, Kenneth, Matthew; LUND, Kate-Iyn; SINKO, Bill; SPROTT, Kevin; (418 pag.)WO2018/13867; (2018); 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 5335-05-7 as follows. category: esters-buliding-blocks

Under nitrogen protection,The racemic mixture of 3- (indol-3-yl) -butyric acid or S-3-iv)(0 · 20 g, 1 mmol)And triethylamine (0 · 10 g, 1 mmol)Dissolved in DMF solution (6ml) solution at room temperature for 5min,Then methyl chlorobenzoate (0.17 g, 1 mmol),The reaction at room temperature 24h, after the reaction was added ethyl acetate 50ml,The ethyl acetate layer was washed with water (80 ml X 3) and the ethyl acetate layer was dried over anhydrous Na 2 SO 4. After the solvent was removed by column chromatography, the target compound 3- (3-indol-3-yl) Methyl ester (0.23 g, 70%),Which is a racemic mixture or (S) isomer.

According to the analysis of related databases, 5335-05-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Bio-technology Institute; Liu Zongying; Li Zhuorong; Jin Jie; Zhu Juntai; (111 pag.)CN103664996; (2017); B;,
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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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 56741-34-5

General procedure: To a solution of 11a (500 mg, 1.85 mmol) in acetone (10 mL) was added 12 (380 mg, 1.85 mmol) and pyridine (0.45 mL, 5.54 mmol).The mixture was stirred at 55 C for 1 h. The mixture was concentrated,diluted with ethyl acetate and washed with 1M HCl and brine twice.Then, the ethyl acetate layer was dried over anhydrous sodium sulfate andconcentrated to give the crude product. The crude product was purified bysilica column eluting with petroleum ether/ethyl acetate (5/1-2/1) to givethe desired product (0.33 g, yield 44.3%) as grey 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 56741-34-5.

Reference:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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. category: esters-buliding-blocks

[0511] 5-Chlorosalicylaldehyde (20.02 g, 0.128 mole) and ethyl 4,4, 4-trifluorocrotonate (23.68 g, 0.14 mole) were dissolved in anhydrous DMF, warmed to 60 C and treated with anhydrous K2CO3 (17.75 g, 0. 128 mole). The solution was maintained at 60 C for 20 hours, cooled to room temperature, and diluted with water. The solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous MGS04, filtered and concentrated in vacuo to afford 54.32 g of an oil. The oil was dissolved in 250 mL of methanol and 100 mL of water, whereupon a white solid formed that was isolated by filtration. The resulting solid was washed with water and dried in vacuo, to afford the ester as a yellow solid (24.31 g, 62%): mp 62-64 C. 1H NMR (CDC13/90 MHz) 7.64 (s, 1H), 7.30-7. 21 (m, 2H), 6.96 (d, 1H, J= Hz), 5.70 (q, 1H, J= Hz), 4.30 (q, 2H, J= 7.2 Hz), 1.35 (t, 3H, J=7.2 Hz).

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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Electric Literature of 37466-90-3, These common heterocyclic compound, 37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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: To a mixture of 2-pyridine aldehyde (5a, 107 mg, 1mmol) and 1,2-diaminobenzene (6a, 108 mg, 1 mmol) in ethanol (25 mL)was added an aqueous solution of sodium pyrosulfite (1.52g, 8 mmol, 5 mL) and refluxed for 4 to 6 h, until the TLC indicated that reaction was completed. The reaction mixture was concentrated under vacuum and the residue was dissolved in CHCl3 (2 x15 mL) and washed with water. The combined organic phases were dried over anhydrousNa2SO4, filtered and the solvent was removed under vacuumand purified by column chromatography (70% EtOAc-hexane) to afford compound 7a as a brown solid.

The synthetic route of 37466-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Pogula, Praveen Kumar; Khan, Mohammed Naseer Ahmed; Seshadri, Bobburi Naga; Sreekanth, Kokkonda; Medicinal Chemistry; vol. 9; 5; (2013); p. 651 – 659;,
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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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl 2-bromopropanoate

CS2CO3 (622mg, l.9lmmol) was added to a stirred mixture of tert- butyl 3-(5,6- dimethoxythieno[3,2-b]pyridin-2-yl)-3-oxopropanoate (322mg, 0.954mmol) in DMF (3mL) at 25C. A mixture of fer/-butyl 2-bromopropanoate (2l0mg, l.OOmmol) in DMF (lmL) was added dropwise to the reaction mixture. The reaction mixture was stirred at RT for 5 hours. Additional /er/-butyl 2-bromopropanoate (63mg, 0.030mmol) was added, and the reaction mixture was stirred for 1 hour. Additional /er/-butyl 2-bromopropanoate (63mg, 0.030mmol) was added, and the reaction mixture was stirred overnight. The reaction mixture was diluted with isopropyl acetate (75mL) and sodium citrate (10% w/v in H20, 40mL). The layers were separated, and the aqueous layer was extracted with additional isopropyl acetate (40mL). The organic layers were combined, washed with brine, dried over anhydrous Na^SCri. filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting EtOAC in Hex) to afford di-/er/-butyl 2-(5,6-dimethoxythieno[3,2-b]pyridine-2- carbonyl)-3-methylsuccinate. LCMS (C23H32NO7S) (ES, m/z): 466 [M+H]+.

According to the analysis of related databases, 39149-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CASH, Brandon, D.; CUMMING, Jared, N.; DEMONG, Duane, E.; HAIDLE, Andrew, M.; JEWELL, James, P.; LARSEN, Matthew, A.; LU, Min; OTTE, Ryan, D.; TAOKA, Brandon, M.; TROTTER, Benjamin Wesley; TRUONG, Quang, T.; (97 pag.)WO2019/195063; (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 36692-49-6 as follows. Product Details of 36692-49-6

A mixture of methyl 3,4-diaminobenzoate (8, 830 mg, 5 mmol) and 4-methoxy benzaldehyde (9a, 680 mg, 5 mmol) in ethanol (25 mL) was heated with an aqueous solution of sodium pyrosulfite (1.42 g, 1.5 mmol, 5 mL) and then refluxed for 4-6 h, until TLC indicated that the reaction was complete. The ethanol was evaporated under vacuum and the residue was dissolved in CHCl3 (2 * 15 mL) and washed with water. The combined organic phases were dried over anhydrous Na2SO4, and the solvent was removed under vacuum and purified by column chromatography MeOH-CH2Cl2 (0.5:9.5) to obtain the pure product 10a as a white solid (952 mg, 68%); mp: 231-234 C; 1H NMR (500 MHz, CDCl3): delta 8.28 (s, 1H), 8.12 (d, J = 9.1 Hz, 2H), 7.92 (d, J = 9.0 Hz, 1H), 7.12 (d, J = 8.3 Hz, 1H), 6.98 (d, J = 8.3 Hz, 2H), 3.94 (s, 3H), 3.85 (s, 3H); MS (ESI): m/z 283 [M + H]+.

According to the analysis of related databases, 36692-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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These common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, 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. SDS of cas: 5445-17-0

(No.)-Cis-2- ( 4-[4-(acetyl-phenyl-amino)-2-methyl-3 ,4-dihydro-2H-quinoline- I -carbonyl]- phenylamino} -propionic acid methyl ester was prepared from (No.)-cis-N-[1-(4-amino-benzoyl)-2- methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. A mixture of (No.)-cis-N-[1-(4- amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide (210 mg, 0.53 mmol), potassium carbonate (123 mg, 0.89 mmol), and methyl 2-bromopropionate (70 uL, 0.63mmol) in dry dimethylformamide (2 mL) was heated at 100C for 6h, then cooled to room temperature and stirred with 20ml water until all of the salts dissolved. The aqueous layer was separated and was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting oil was purified by silica gel chromatography, eluting with (97: 3 methylene chloride/methanol) to afford the title compound (220 mg, 87%). ‘H-NMR (CDC13) 8: 1.2 (4H, m), 1.4 (3H, d), 2.0 (3H, s), 2.3 (1H, br), 3.7 (3H, s), 4.1 (1H, m), 4.7 (1H, m), 5.6 (1H, br), 6.3 (2H, d), 6.6 (1H, d), 6.9 (1H, m), 7.0 (2H, d), 7.3-7.4 (7H, m). MS m/z: 487 (M+2).

The synthetic route of Methyl 2-bromopropanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2005/100321; (2005); A1;,
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