Category: 73792-08-2

These common heterocyclic compound, 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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. Formula: C8H8FNO2

General procedure: The obtained compound was dissolved in methylene chloride, and the solution was cooled to -10 C. Then, a methylene chloride solution (200 ml) of methyl 4-amino-2-fluorobenzoate (16.9 g, 100 mmol) and pyridine (10 ml) was added thereto, followed by stirring at room temperature for 2 hours. The reaction solution was washed with 0.1 N hydrochloric acid (200 ml×2). Then, the organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=2:1 to 1:1) to obtain the title compound (12.4 g, 40%). [0715] MS (ESI) m/z 311 (M+H)+

The synthetic route of Methyl 4-amino-2-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
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73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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. Formula: C8H8FNO2

Add in a 150 mL two-necked flask at room temperature 2-fluoro-4-aminobenzoic acid ester 2 (4.5 g, 26.6 mmol), acetone (2.99 g, 42.7 mmol), potassium cyanide (2.6 g, 40 mmol) and 46 mL of acetic acid, the mixture was heated to 75 C for 24 h, and the reaction was monitored by TLC ( petroleum ether: ethyl acetate = 20:3). After the reaction was completed, 20 mL of water was added to the reaction mixture, and ethyl acetate (40×3 mL) was evaporated.The residue was dissolved by adding a mixed solvent of 6 mL of ethanol and 5 mL of water. cooling crystals, filtering to give compound 21, 3.13 g, yellow solid, yield 50.2%.

The synthetic route of 73792-08-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changsha Zeda Pharmaceutical Technology Co., Ltd.; Chen Yongheng; Xu Guangyu; Zhou Wenqiang; (23 pag.)CN108976171; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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 73792-08-2, COA of Formula: C8H8FNO2

A suspension of 5,6,7,7a,8,9,10, 11-octahydro-4H-2-benzo[ef]heptalenecarboxylic acid (0.090 g) in anhydrous benzene (3 ml) was added with thionyl chloride (1 ml), and the mixture was refluxed by heating for 3 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in anhydrous benzene (2 ml) and pyridine (5 ml), the solution was added with methyl 2-fluoro-4-aminobenzoate (0.075 g) and 4-dimethylaminopyridine (one pellet), and the mixture was stirred overnight. The reaction mixture was added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, 10% aqueous sodium carbonate, and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane = 1:10) to obtain methyl 2-fluoro-4-[(5,6,7,7a,8,9,10,11-octahydro-4H-2-benzo[ef]heptaleny)carboxamido]benzoate (0.052 g, yield: 36%). 1H-NMR (400MHz, CDCl3): delta 1.51-1.71 (6H, m), 1.79-1.95 (6H, m), 2.91 (4H, t, J=5.7 Hz), 3.26-3.32 (1H, m), 3.92 (3H, s), 7.31 (1H, dd, J=8.4, 2.1 Hz), 7.41 (2H, s), 7.77 (1H, dd, J=12.9, 2.1 Hz), 7.94 (1H, br-s), 7.95 (1H, t, J=8.4 Hz)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Research Foundation Itsuu Laboratory; EP2189443; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 73792-08-2

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to a pyridine (500 ml) solution of 18.9 g of methyl 4-amino-2-fluorobenzoate and 16.5 g of picolinic acid, and stirred at room temperature for 2 hours. The solvent was evaporated away under reduced pressure, 600 ml of ethyl acetate was added to the residue, the organic layer was washed with aqueous 0.25 N hydrochloric acid solution, aqueous 0.25 N sodium hydroxide solution and saturated saline water, dried, concentrated under reduced pressure, solidified from a mixed solvent of hexane/ethyl acetate, and the solid was taken out through filtration. This was dried under reduced pressure to obtain 28.3 g of the entitled compound as a white solid.

The synthetic route of 73792-08-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1810969; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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 73792-08-2, Application In Synthesis of Methyl 4-amino-2-fluorobenzoate

General procedure: A solution of (7: R1=cyclopentyloxy) (100mg, 363mumol) in dichloromethane (5 mL), cooled to 0C, was treated with oxalyl chloride (63.6 muL, 727 mumol), followed by a drop of N,N-dimethylformamide. The resultant mixture was stirred for 1h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in dichloromethane (5 mL) and then treated with a solution of methyl 4-aminobenzoate (8: R2=H, R=Me) (54.9mg, 363mumol) and di-isopropylethylamine (190muL, 1.09mmol) in dichloromethane (5mL). The reaction mixture was stirred for 12 h at room temperature and then partitioned between dichloromethane (20 mL) and aqueous 1M hydrochloric acid (20 mL). The phases were separated, and the organic phase was washed successively with water (2¡Á20 mL), and brine (20 mL), dried over magnesium sulfate, filtered and then the solvent was removed in vacuo. The residue was purified by silica gel chromatography (12 g, 0-100 % ethyl acetate/isohexane) to afford methyl 4-[3,5-dichloro-4-(cyclopentyloxy)benzamido]benzoate (10: R1 = cyclopentyloxy, R2 = H, R =Me) (30mg, 20% yield). 1H NMR (400MHz, CDCl3) delta 8.06 (2H, d, J=8.8Hz,), 7.85 (1H, br s), 7.82 (2H, s), 7.71 (2H, d, J=8.8Hz), 5.07-5.03 (1H, m), 3.92 (3H, s), 2.10-1.90 (4H, m), 1.85-1.70 (2H, m), 1.70-1.60 (2H, m).

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 4-amino-2-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 73792-08-2, 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. 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 7Synthesis of 2-cyano-3-(2-fluoro-4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)-dimethylacrylamideStep 1To a 250 ml three necked round bottom flask, methyl 4-amino-2-fluorobenzoate (2.75 g, 0.0162 mole) was added in anhydrous THF (60 ml) under nitrogen atmosphere and cooled to 0- 5 C. After 15 minutes, 2.0 M solutions of LAH in THF (24.3 ml, 0.0487 mole) was added dropwise and stirred for 10 min. The reaction mixture was allowed to warm up to room temperature and stirred at same temperature for 1 hr. After completion of the reaction, the reaction mixture was cooled to 5 C and quenched with sat. NH4C1 (25 ml) and diluted with water (100 ml) followed by extraction with ethyl acetate. The combined organics were washed with water, dried over sodium sulphate and evaporated to afford brown solid (crude) product which was purified using column purification by eluting the compound with 20% ethyl acetate in hexanes to yield 1.7 g of (4-amino-2-fluorophenyl)methanol.

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 4-amino-2-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; VERNER, Erik; WO2012/158785; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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 73792-08-2, name: Methyl 4-amino-2-fluorobenzoate

Add 2-fluoro-4-aminobenzoic acid methyl ester 2 (3.70 g, 21.8 mmol), cyclobutanone (2.44 g, 34.8 mmol), potassium cyanide (2.12 g, 32.6 mmol) and 37 mL to a 250 mL two-necked flask. Acetic acid, the temperature was raised to 80 C for 12 h, TLC monitoring reaction, (petroleum ether: ethyl acetate = 20:3), after the reaction was completed, 20 mL of water was added to the reaction solution, ethyl acetate extraction (30 ¡Á 3 mL), decompression In addition to the solvent, Compound 3, 5.01 g, brown red solid, yield: 92.5%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Changsha Zeda Pharmaceutical Technology Co., Ltd.; Chen Yongheng; Xu Guangyu; Zhou Wenqiang; (23 pag.)CN108976171; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

73792-08-2, These common heterocyclic compound, 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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 the compound of Reference Example 11-1 (358 mg, 1.20 mmol) in dichloromethane (4 mL), oxalyl chloride (113 muL, 1.32 mmol) and DMF (5 muL) were added at 0C, and the mixture was stirred for 20 minutes. To the reaction solution, a solution of methyl 4-amino-2-fluorobenzoate (105.4 mg, 0.623 mmol) and diisopropylethylamine (310 muL, 1.80 mmol) in dichloromethane (2 mL) was added at 0C, and the mixture was stirred for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated saline solution, then dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the title compound (83.2 mg, 30%). MS (ESI+) 449 (M+1, 84%)

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 73792-08-2.

Reference:
Patent; Sumitomo Dainippon Pharma Co., Ltd.; IKUMA Yohei; FUKUDA Nobuhisa; IWATA Masato; KIMURA Hidenori; SUZUKI Kuniko; EP2876105; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics