Category: 455-75-4

Electric Literature of 455-75-4, A common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

Intermediate 33: N-{5-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; Step A: Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-4-fluorobenzoate; To a solution of ethyl 3-amino-4-fluorobenzoate (5.47 g, 30 mmol) and pyridine (2.55 mL, 33 mmol) in DCM (150 mL) was added 2,6-difluorobenzenesulfonyl chloride (4.45 mL, 33 mmol). The reaction was stirred overnight at rt. After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7.87 g (66% yield) of the product of Step A as a white powder. MS (ESI): 360 (M+H).

The synthetic route of 455-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-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: C9H10FNO2

To a stirred solution of [3-(1, 1-DIMETHYLETHYL)-1-ETHYL-4, 5-DIHYDRO-LH-PYRAZOLE-] 5-carboxylic acid (i. e. the product of Step D) (0.8 g, 4.1 mmol) in dichloromethane (5 mL) was added 1-propanephosphonic acid cyclic anhydride (50 wt % solution in ethyl acetate, 3.9 g, 6.14 mmol) followed by 4- (dimethylamino) pyridine [(0. 75] g, 6.14 mmol). After stirring for 1 h, ethyl [3-AMINO-4-FLUOROBENZOATE] (0.68 g, 3.7 mmol) was added, and the resulting solution was stirred at room temperature overnight. The solvent was removed in vacuo and partitioned between water (50 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (30 mL). The organic layer was washed with aqueous saturated sodium bicarbonate (50 mL) and water (50 mL), and dried [(MGSO4).] The solvent was removed in vacuo to provide the title product, a compound of the present invention, as an oil (1.36 g). 1H NMR (CDC13): [B] 9.3 (s, 1H), 8.95 (d, 1H), 7.80 (m, 1H), 7.16 (t, 1H), 3.70 (t, 1H), 3.33 (dd, 1H), 3.18 (dq, 1H), 2.95 (dq, 1H), 2.83 (dd, 1H), 1.39 (t, 3H), 1.21 (t, 3H), 1.17 (s, 9H).

The synthetic route of Ethyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; WO2004/35545; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 455-75-4, A common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

The 17.4g (94.9mmol) 3-amino-4-fluoro-benzoic acid ethyl ester (reference L.S.Fosdick, A.F.Dodds, J.Amer Chem.Soc. 65,2305 (1943)) and 9.67 ml (11.47g, 105 . 4mmol) methoxy acetyl chloride then 310 ml of chlorobenzene to the solution in the 50 C stirring 2 hours, then reflux 30 minutes. Concentrated under reduced pressure to dryness, purified by silica gel column chromatography (dichloromethane/ethanol = 100:1), oily product to be 3-amino-4-fluoro-benzoic acid ethyl ester, after a few days is cured into a solid (20.1g, yield 83%). R f value: 0.38 (silica gel: dichloromethane/ethanol = 19:1). Mass spectrometric (ESI-MS): 256.1(M+H) +, 278.1(M+Na) +; C 12 H 14 FNO 4 (255).

The synthetic route of 455-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xizang Hai Sike Pharmaceutical Group Co., Ltd.; Li Qilin; Li Yue; Dang Juan; Long Yu; (53 pag.)CN103524559; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 455-75-4, A common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

Intermediate 33: N-{5-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; Step A: Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-4-fluorobenzoate; To a solution of ethyl 3-amino-4-fluorobenzoate (5.47 g, 30 mmol) and pyridine (2.55 mL, 33 mmol) in DCM (150 mL) was added 2,6-difluorobenzenesulfonyl chloride (4.45 mL, 33 mmol). The reaction was stirred overnight at rt. After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7.87 g (66% yield) of the product of Step A as a white powder. MS (ESI): 360 (M+H).

The synthetic route of 455-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

455-75-4, These common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-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.

a Ethyl 4-fluoro-3-methoxyacetamido-benzoate A solution of 2.8 g (15.3 mMol) of ethyl 3-amino-4-fluoro-benzoate (cf. L. S. Fosdick, A. F. Dodds in J. Amer. Chem. Soc. 65, 2305 (1943)) and 1.56 ml (1.85 g=17.0 mMol) of methoxyacetylchloride in 50 ml chlorobenzene was stirred for 1 hour at 50 C. and then refluxed for 15 minutes. Then the solvent was distilled off in vacuo and the crude product obtained was purified by flash chromatography (silica gel; dichloromethane/ethanol=100:1). The desired compound, initially oily, solidified within a few days. Yield: 3.8 g (98% of theory), Rf value: 0.38 (silica gel; dichloromethane/ethanol=19:1)

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 455-75-4.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6087380; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

455-75-4, A common compound: 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of ethyl 3-amiotano-4-fluorobenzoate (547 g, 30 mmol) and pyridine (2 55 mL, 33 mmol) in DCM (150 mL) was added 2,6-diotafluorobenzenesulfonyl chloride (4 45 mL, 33 mmol) The reaction was stirred overnight at rt After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7 87 g (66% yield) of the product of Step A as a white powder ES-LCMS m/z 360 (M+H)

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

Reference:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics