Category: 652-39-1

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.652-39-1,4-Fluoroisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

652-39-1, To a stirred solution of 4-fluoroisobenzofuran-1,3-dione (25 g, 150 mmol, CAS652-39-1) in DMF (100 mL) was added L-glutamine (22 g, 150 mmol) at rt. The resulting reaction mixture was heated to at 90 C. and stirred for 2 h. The reaction mixture was then evaporated under reduced pressure, transferred into 4 N aqueous HCl solution and the resulting mixture was stirred for 36 h at rt. The solid precipitate was then filtered off, washed with cold water and dried under reduced pressure to give 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid as a white solid (28 g, 63%). LC-MS (ESI+) m/z 295 (M+H)+.

The synthetic route of 652-39-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

652-39-1, 4-Fluoroisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

652-39-1, 3-fluoropurine (5.0 g, 30 mmol),3-aminopiperidine-2,6-dione hydrochloride (5.0 g, 30 mmol) andSodium acetate(3.7g, 45mmol)Add 100 mL of acetic acid. Heat to reflux for 12 h.Cool to room temperature and evaporate the acetic acid. Add 100 mL of water, extract 100 mL¡Á3 of ethyl acetate, and combine the organic phases with evaporated toluness.The compound (1a) was obtained in an amount of 7.5 g, and the yield was 90%.

652-39-1 4-Fluoroisobenzofuran-1,3-dione 69551, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Jilin University; Lu Haibin; Mu Xupeng; Bai Liting; Gao Zhuolin; Wang Ying; Zhao Linxuan; (23 pag.)CN109879877; (2019); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

652-39-1,652-39-1, 4-Fluoroisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Fluorophthalic anhydride (377 mg, 2.27 mmol) was dissolved in MeOH (6 ml_) and heated to reflux for 15 h. The mixture was concentrated in vacuo and the two products (400 mg, 89percent), 2-fluoro-6-(methoxycarbonyl)benzoic acid and 3-fluoro-2- (methoxycarbonyl)benzoic acid, were taken on to the next step without purification.; Step B: (Z)-Methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-3- fluorobenzoate. To a heterogeneous mixture of the two acids from step A (400 mg, 2 mmol) at 0 ¡ãC in DCM (5 ml_) was added oxalyl chloride (0.244 ml_, 2.32 mmol) followed by DMF (0.05 ml_). Gas evolution commenced immediately and after 5 min the ice bath was removed. When gas evolution had ceased and the mixture was homogeneous an aliquot was removed and quenched with MeOH. Formation of the methyl ester was confirmed by HPLC and the mixture was concentrated in vacuo. The viscous liquid was dissolved in fresh DCM (5 ml_) and treated with solid N-hydroxyacetamidine (165 mg, 2.22 mmol) in several portions followed by TEA (0.351 ml_, 2.52 mmol). After stirring for 14 h at ambient temperature the mixture was concentrated in vacuo.Chromatography (Hex to 100percent EtOAc/Hex) afforded two products (477 mg, 94percent), (Z)-methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-3- fluorobenzoate and (Z)-methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-6- fluorobenzoate, which were taken on to the next step as a mixture. MS (ESI) mass calculated for Cn H FN2O4, 254.07; m/z found, 255.0.

As the paragraph descriping shows that 652-39-1 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

652-39-1, 4-Fluoroisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

652-39-1, A mixture of the above 4-fluoroisobenzofuran-1,3-dione (40 g, crude) and L-glutamine (35 g, 239 mmol) in dry DMF (200 mL) was stirred at 90 for 8 h. The solvent was removed under reduced pressure. The residue was re-dissolved in 4N HCl (200 mL) and stirred for additional 8 h. The resulting precipitation was collected by filtration, washed with water, and dried to afford 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid (37 g, crude) as an off-white solid. LC-MS: 295.2 [MH]+.1H NMR (400 MHz, CDCl3): delta 2.16-2.20 (m.2H), 2.31-2.43 (m, 2H), 4.79-4.83 (m, 1H), 6.79 (br, 1H), 7.26(br, 1H), 7.77-7.85 (m, 2H), 7.98-8.03 (m, 1H), 13.32(br, 1H).

The synthetic route of 652-39-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; YALE UNIVERSITY; CREWS, Craig M.; BURSLEM, George; CROMM, Philipp M.; JAIME-FIGUEROA, Saul; TOURE, Momar; (279 pag.)WO2019/148055; (2019); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

652-39-1, 4-Fluoroisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

652-39-1, A mixture of 3 -fluorophthalic anhydride (1 equiv.), 9-amino-S -(4-methoxybenzyl)-2-oxa- 6-thia-5-azaspiro[3.5]nonane 6,6-dioxide (1 equiv.), and potassium acetate (2.5 equiv.) in acetic acid is stirred at 120 ¡ãC overnight. The dark mixture is cooled and filtered. The filter cake is dissolved in DCM and washed with saturated NaHCO3 and brine. The organic layer is dried (Na2 SO4) and concentrated to provide 4-fluoro-2? -oxetano-6? -sulfonyl-thalidomide.

As the paragraph descriping shows that 652-39-1 is playing an increasingly important role.

Reference£º
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; MICHAEL, Ryan, E.; (790 pag.)WO2017/197056; (2017); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.652-39-1,4-Fluoroisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

652-39-1, The best result occurs when the starting material is run 0.5 M in formamide and heated to 125 ¡ãC for 1 to 5 h depending on scale. Starting material is not soluble in fonnamide until the temperature is > 60 ¡ãC. Upon completion of reaction as monitored by LC/MS (apcineg), the heat is removed and 3 times the volume of the reaction of water is added. Next, the reaction is allowed to warm to room temperature and stirred until a pale yellow precipitate has formed. The yellow solid product is filtered off and washed with water before drying overnight to give yields between 70-77 percent.

As the paragraph descriping shows that 652-39-1 is playing an increasingly important role.

Reference£º
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA INC.; WO2005/37214; (2005); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

652-39-1,652-39-1, 4-Fluoroisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Fluorophthalic anhydride (377 mg, 2.27 mmol) was dissolved in MeOH (6 ml_) and heated to reflux for 15 h. The mixture was concentrated in vacuo and the two products (400 mg, 89percent), 2-fluoro-6-(methoxycarbonyl)benzoic acid and 3-fluoro-2- (methoxycarbonyl)benzoic acid, were taken on to the next step without purification.; Step B: (Z)-Methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-3- fluorobenzoate. To a heterogeneous mixture of the two acids from step A (400 mg, 2 mmol) at 0 ¡ãC in DCM (5 ml_) was added oxalyl chloride (0.244 ml_, 2.32 mmol) followed by DMF (0.05 ml_). Gas evolution commenced immediately and after 5 min the ice bath was removed. When gas evolution had ceased and the mixture was homogeneous an aliquot was removed and quenched with MeOH. Formation of the methyl ester was confirmed by HPLC and the mixture was concentrated in vacuo. The viscous liquid was dissolved in fresh DCM (5 ml_) and treated with solid N-hydroxyacetamidine (165 mg, 2.22 mmol) in several portions followed by TEA (0.351 ml_, 2.52 mmol). After stirring for 14 h at ambient temperature the mixture was concentrated in vacuo.Chromatography (Hex to 100percent EtOAc/Hex) afforded two products (477 mg, 94percent), (Z)-methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-3- fluorobenzoate and (Z)-methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-6- fluorobenzoate, which were taken on to the next step as a mixture. MS (ESI) mass calculated for Cn H FN2O4, 254.07; m/z found, 255.0.

652-39-1 4-Fluoroisobenzofuran-1,3-dione 69551, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.652-39-1,4-Fluoroisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

652-39-1, 3-Fluorophthalic anhydride (377 mg, 2.27 mmol) was dissolved in MeOH (6 ml_) and heated to reflux for 15 h. The mixture was concentrated in vacuo and the two products (400 mg, 89percent), 2-fluoro-6-(methoxycarbonyl)benzoic acid and 3-fluoro-2- (methoxycarbonyl)benzoic acid, were taken on to the next step without purification.; Step B: (Z)-Methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-3- fluorobenzoate. To a heterogeneous mixture of the two acids from step A (400 mg, 2 mmol) at 0 ¡ãC in DCM (5 ml_) was added oxalyl chloride (0.244 ml_, 2.32 mmol) followed by DMF (0.05 ml_). Gas evolution commenced immediately and after 5 min the ice bath was removed. When gas evolution had ceased and the mixture was homogeneous an aliquot was removed and quenched with MeOH. Formation of the methyl ester was confirmed by HPLC and the mixture was concentrated in vacuo. The viscous liquid was dissolved in fresh DCM (5 ml_) and treated with solid N-hydroxyacetamidine (165 mg, 2.22 mmol) in several portions followed by TEA (0.351 ml_, 2.52 mmol). After stirring for 14 h at ambient temperature the mixture was concentrated in vacuo.Chromatography (Hex to 100percent EtOAc/Hex) afforded two products (477 mg, 94percent), (Z)-methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-3- fluorobenzoate and (Z)-methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-6- fluorobenzoate, which were taken on to the next step as a mixture. MS (ESI) mass calculated for Cn H FN2O4, 254.07; m/z found, 255.0.; Step C: 3-Fluoro-2-(3-methyl-1 ,2,4-oxadiazol-5-yl)benzoic acid. To the mixture of products from Step B (477 mg, 1 .88 mmol) in t-BuOH (9 ml_) was added NaOAc (156 mg, 1 .88 mmol). The mixture was heated at 90 ¡ãC for 50 h and then concentrated in vacuo. This resulted in four products. The residue was dissolved in 1 M aq. K2CO3 and extracted with DCM to isolate methyl 2- fluoro-6-(3-methyl-1 ,2,4-oxadiazol-5-yl)benzoate and methyl 3-fluoro-2-(3- methyl-1 ,2,4-oxadiazol-5-yl)benzoate along with unreacted (Z)-methyl 2-((((1 – aminoethylidene)amino)oxy)carbonyl)-3-fluorobenzoate. The aqueous layer was then acidified with concentrated HCI and extracted with DCM. The combined organic layers from this extraction were dried over Na2SO4, filtered and concentrated in vacuo. The acid isomers were purified on a Prep Agilent system with a XBridge Ci8 OBD 50×100 mm column eluting with 5 to 99percent 0.05percent NH4OH in H2O/ACN over 17 min to afford the desired product (63 mg, 15percent) as a white solid after acidification with 1 M aq. HCI in Et2O. MS (ESI) mass calculated for C10H7FN2O3, 222.04; m/z found, 223.0.; Intermediate 69: 2-Fluoro-6-(3-methyl-1 ,2,4-oxadiazol-5-yl)benzoic acid.The title compound was isolated from the synthesis of Intermediate 68, Method A. MS (ESI) mass calculated for Ci0H7FN2O3, 222.04; m/z found, 223.0. 1H NMR (500 MHz, CDCI3): 7.89 (d, J = 7.7, 1 H), 7.65 – 7.59 (m, 1 H), 7.44 – 7.38 (m, 1 H), 2.50 (s, 3H).

The synthetic route of 652-39-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

652-39-1, 4-Fluoroisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

652-39-1, Step 1: Synthesis of 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione A solution of 4-fluoroisobenzofuran-1,3-dione (200 mg, 1.20 mmol, 1 equiv) in AcOH (4.0 mL, 0.3 M) was added 2,6-dioxopiperidin-3-amine hydrochloride (218 mg, 1.32 mmol, 1.1 equiv) and potassium acetate (366 mg, 3.73 mmol, 3.1 equiv). The reaction mixture was heated to 90 oC overnight, whereupon it was diluted with water to 20 mL and cooled on ice for 30 min. The resulting slurry was filtered, and the black solid was purified by flash column chromatography on silica gel (2% MeOH in CH2Cl2, Rf = 0.3) to afford the title compound as a white solid (288 mg, 86%). 1H NMR (500 MHz, DMSO-d6) delta 11.15 (s, 1H), 7.96 (ddd, J = 8.3, 7.3, 4.5 Hz, 1H), 7.82 – 7.71 (m, 2H), 5.17 (dd, J = 13.0, 5.4 Hz, 1H), 2.90 (ddd, J = 17.1, 13.9, 5.4 Hz, 1H), 2.65- 2.47 (m, 2H), 2.10- 2.04 (m, 1H), MS (ESI) cald for C13H10FN2O4 [M+H]+ 277.06, found 277.25.

As the paragraph descriping shows that 652-39-1 is playing an increasingly important role.

Reference£º
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BUCKLEY, Dennis; WINTER, Georg; PHILLIPS, Andrews, J.; HEFFERNAN, Timothy, P.; BRADNER, James; ROBERTS, Justin; BEHNAM, Nabet; (544 pag.)WO2018/148443; (2018); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

652-39-1, 4-Fluoroisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

652-39-1, General procedure: To a solution of compounds 2a-2h (5 mmol) in acetic anhydride (5 mL) and triethylamine (2.5 mL) was added ethyl acetoacetate (0.71 mL, 5.5 mmol) under argon. The reaction mixture was stirred at rt for 12 h and then poured into the mixture of concentrated HCl (6 g) and ice-water (6 g). After that, the reaction mixture was stirred at rt for 30 min, additional HCl (8.8 mL, 5M) was added into the mixture, and then the reaction mixture was refluxed for 2 h. After the crude product was cooled to rt, water (100 mL) was added and the reaction mixture was extracted with DCM (2 100 mL). The combined organic layers were washed with brine and then dried (Na2SO4). After removing the solvent, the residue was purified by flash column chromatography.

As the paragraph descriping shows that 652-39-1 is playing an increasingly important role.

Reference£º
Article; Guo, Shenquan; Zhang, Niuniu; Tang, Xiangzheng; Mao, Zhifeng; Zhang, Xuejing; Yan, Ming; Xuan, Yining; Chinese Chemical Letters; vol. 30; 2; (2019); p. 406 – 408;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem