Day: November 11, 2020

37418-88-5, 4-Hydroxyisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 16 5-(4-Methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(oxalyl-amino)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid; To a solution of 4-hydroxy-isobenzofuran-1,3-dione (195 mg, 1.2 mmol) in anhydrous N,N-dimethylformamide (4 ml) under nitrogen was added minutes and then methyl iodide (0.37 ml, 6.0 mmol) was added. The reaction was stirred for 48 h. and then quenched with saturated ammonium chloride. The mixture was concentrated in vacuo, diluted in ethyl acetate (20 ml) and the organic phase washed with 1N hydrochloric acid (5 ml) and brine (3.x.5 ml). The organic layer was dried (MgSO4) and concentrated in vacuo. To the crude solid was added methanol causing a precipitate to form. The flask was cooled in an ice bath for 2 h. and the solid filtered off, washed with methanol and dried in vacuo which afforded 0.1 g (47percent) of 4-methoxy-isobenzofuran-1,3-dione as a solid.1H NMR (300 MHz, DMSO-d6) delta 7.95 (t, J=8, 1H), 7.61 (d, J=8, 1H), 7.58 (d, J=8, 1H), 3.99 (s, 3H).APCI-MS: [M+H]+=179.1A solution of 2-amino-5-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (122 mg, 0.43 mmol, prepared as described in Example 17) and 4-methoxy-isobenzofuran-1,3-dione (92 mg, 0.52 mmol) was prepared in distilled tetrahydrofuran (4 ml) under nitrogen. 1-hydroxybenzotriazole (87 mg, 0.65 mmol), 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (123 mg, 0.65 mmol), and triethylamine (0.29 ml, 2.15 mmol) were added. The reaction was stirred at ambient temperature for 18 h., then concentrated in vacuo. The crude mixture was diluted with ethyl acetate (25 ml) and washed with 1N hydrochloric acid (5 ml), saturated sodium bicarbonate (5 ml), and brine (5 ml). The organic layer was dried (Na2SO4), filtered, and the solvent evaporated in vacuo to give 0.18 g (94percent) of 2-amino-5-(4-methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester.1H NMR (300 MHz, CDCl3) delta 7.66 (t, J=7, 1H), 7.43 (d, J=7, 1H), 7.19 (d, J=7, 1H), 4.59-4.46 (m, 2H), 4.06-3.72 (m, 3H), 4.00 (s, 3H), 2.87-2.81 (m, 1H), 2.60-2.51 (m, 1H), 1.48 (s, 9H).To a solution of the above 2-amino-5-(4-methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.18 g, 0.42 mmol) in distilled dichloromethane (5 ml) under nitrogen was added imidazol-1-yl-oxo-acetic acid tert-butyl ester (0.25 g, 1.26 mmol) and triethylamine (0.23 ml, 1.68 mmol). The reaction was stirred for 12 h., concentrated in vacuo and reconstituted in ethyl acetate (25 ml). The organic layer was washed with 1N hydrochloric acid (2.x.5 ml), saturated sodium bicarbonate (5 ml), and brine (5 ml). The resulting solution was dried (Na2SO4), filtered, and the solvent evaporated in vacuo. The crude material was purified by silica gel chromatography using a gradient of ethyl acetate/dichloromethane (0 to 10percent gradient). Pure fractions were collected and the solvent evaporated in vacuo to give 195 mg (81percent) of 2-(tert-butoxyoxalyl-amino)-5-(4-methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as an oil.1H NMR (300 MHz, CDCl3) delta 12.48 (s, 1H), 7.65 (t, J=7, 1H), 7.43 (d, J=7, 1H), 7.19 (d, J=7, 1H), 4.77 (d, J=15, 1H), 4.63 (d, J=15, 1H), 4.04-3.75 (m, 3H), 4.00 (s, 3H), 2.94 (d, J=17, 1H), 2.65 (dd, J=17, 10, 1H), 1.58 (s, 9H), 1.53 (s, 9H).LC-MS: Rt=4.17 min, [M+H]+=573.2The above 2-(tert-butoxyoxalyl-amino)-5-(4-methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.15 g, 0.26 mmol) was dissolved in a mixture of 50percent trifluoroacetic acid/dichloromethane (5 ml). The reaction was stirred at ambient temperature for 7 h., concentrated in vacuo and the residue evaporated in vacuo from dichloromethane (3.x.10 ml). The resulting precipitate was washed with dichloromethane and dried in vacuo to give 100 mg (83percent) of the title compound as a solid.1H NMR (300 MHz, DMSO-d6) delta 12.31 (s, 1H), 7.79 (t, J=8, 1H), 7.48 (d, J=8, 1H), 7.42 (d, J=8, 1H), 4.74 (d, J=15, 1H), 4.56 (d, J=15, 1H), 3.95 (s, 3H), 3.91-3.79 (m, 2H), 3.69-3.63 (m, 1H), 2.98 (d, J=17, 1H), 2.57 (dd, J=17, 10, 1H).LC-MS: Rt=1.26 min, [M+H]+=461.0HPLC (254.4 nm): Rt=3.10 min, 100percent

37418-88-5, 37418-88-5 4-Hydroxyisobenzofuran-1,3-dione 96580, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Novo Nordisk A/S; US7115624; (2006); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

32703-79-0, 5-(tert-Butyl)isobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-tert-butylphthalic anhydride (4.39 g, 21.5 mmol) in acetic acid (40 mL), 3-bromo-2-methylaniline(2.65 mL, 21.5 mmol) was added and stirred at 100 C for 1 h. The reaction mixture was concentrated under reducedpressure, and diluted with ethyl acetate (300 mL), washed with water (100 mL), saturated sodium hydrogen carbonatesolution (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated. The crude material was suspended in hexane, then the precipitate was collected by filtration, washed with hexane then dried to afford 2-(3-bromo-2-methylphenyl)-5-(tert-butyl)isoindoline-1,3-di one (7.0 g). 1H NMR (400 MHz, CDCl3) delta 8.00 (dd, J = 1.7, 0.7 Hz, 1H), 7.93 – 7.77 (m, 2H), 7.67 (dd, J = 7.6, 1.8 Hz, 1H),7.24 – 7.12 (m, 2H), 2.27 (s, 3H), 1.42 (s, 9H)., 32703-79-0

As the paragraph descriping shows that 32703-79-0 is playing an increasingly important role.

Reference£º
Patent; Carna Biosciences, Inc.; KAWAHATA, Wataru; ASAMI, Tokiko; SAWA, Masaaki; ASAMITSU, Yuko; IRIE, Takayuki; MIYAKE, Takahiro; KIYOI, Takao; EP2824099; (2015); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

64169-34-2, 5-Bromoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0338j Lithium hydroxide (3.45 g, 70.42 mmol, 3.0 equiv) was added at room temperature over several minutes to a solution of 5-bromophthalide (5.0 g, 23.47 mmol, 1.0 equiv) in a 2:1:1 solution of THF/MeOH/ H20 (80 mL) and the reaction mixture was stirred at room temperature for 16 h. After removal of the solvent, the residue was diluted with water (100 mL), adjusted to pH = 3 with HC1 (2 N) and extracted with EtOAc (100 mL x 3). The organic layers were collected, dried (Na2SO4), filtered, and concentrated via rotary evaporator to give title product (3.47 g, yield: 94%) as a white solid, which was used in the next step withoutfurther purification. ESI-MS (M+H) : 231.1. ?H NMR (400 MHz, CD3OD) (5: 7.88-7.86 (m, 2H), 7.45 (dd, J= 8.4, 2.0 Hz, 1H), 4.90 (s, 2H).

64169-34-2, The synthetic route of 64169-34-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

57319-65-0,57319-65-0, 6-Aminoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a cooled solution (0 C) of 6-aminophthalide (5.13 g, 34.05 mmol) in THF (80 ml.) was added /V-bromosuccinimide (6.12 g, 34.05 mmol, 1 eq). The cooling bath was removed and the solution stirred for 1 h, then the solvent was removed under reduced pressure. The yellow residue was taken up in ethyl acetate (400 ml) and washed three times with water (200 ml. each). The organic phase was dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to give 6-amino-7-bromophthalide as a brown solid (6.53 g, 28.63 mmol, 84%). Rf = 0.2 (cyclohexane/ethyl acetate 2:1 ); UPLC-MS: tR = 1.45 min (gradient 10-90% B in 5 min); UPLC-purity (210 nm) = 83.1%; ESI-MS: (calculated MH+: 227.97, 229.96, found: 228.01 , 230.01 )

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BELYNTIC GMBH; ZITTERBART, Robert; REIMANN, Oliver; (102 pag.)WO2020/43747; (2020); 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, A mixture of 3-fluorophthalic anhydride (1 equiv.), 4-amino-1,2-thiazinan-3-one 1,1- 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 (Na2SO4) and concentrated to provide 4- fluoro-6? -sulfonyl-thalidomide.

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

Reference£º
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; HE, Minsheng; MICHAEL, Ryan, E.; (768 pag.)WO2017/197055; (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.59434-19-4,4-Aminophthalide,as a common compound, the synthetic route is as follows.

Example 17D4-(4-(Diethoxymethyl)benzylideneamino)isobenzofuran- 1 (3H)-one[00526] To a stirred mixture of 4-(diethoxymethyl)benzaldehyde (3.75 g, 18 mmol) and anhydrous sodium sulfate (21.3 g, 150 mmol) in anhydrous dichloromethane (300 mL) was added 4- aminoisobenzofuran- l(3H)-one (2.24 g, 15 mmol) at 0 C. After the addition, the mixture was stirred at room temperature for 6 days. The mixture was filtered and the cake was washed with dichloromethane (50 mL*3). The filtrate was concentrated to give crude product. The crude product was washed with petroleum ether to give 4-(4-(diethoxymethyl)benzylideneamino)isobenzofuran-l(3H)-one (4.3 g, yield 84%) as a light yellow solid. LC-MS (ESI) m/z: 340(M+1)+., 59434-19-4

The synthetic route of 59434-19-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; WO2011/130661; (2011); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 25.5 g (0.212 mol) of 2, 3-dihydrobenzofuran in 175 mL of acetic acid was added about one quarter of 4.5 mL (0.227 mol) of 70% aqueous nitric acid dropwise. The reaction was monitored by TLC (EtOAc-hexanes (15: 85) ). The mixture was warmed to 70C where the reaction began. The remainder of the nitric acid was then added while maintaining the reaction at 70C. After 30 minutes, the reaction was cooled and poured into 1.5 L of ice water. The black solid was collected by filtration washing with water. The solid was partitioned between 500 mL of saturated aqueous sodium bicarbonate and 150 mL of EtOAc. The aqueous layer was separated and extracted with three 150 mL portions of EtOAc. The combined organic layers were washed with three 100 mL portions of saturated aqueous sodium bicarbonate, 100 mL of saturated aqueous ammonium chloride, 100 mL of brine, dried over magnesium sulfate, filtered, and concentrated to afford a red oil/solid. The mixture was dissolved in dichloromethane and passed through a pad of silica gel eluting with dichloromethane and concentrated. The resulting red mixture was triturated with ether-hexanes (1: 1) and filtered to afford 10.5 g (29%) of 5-nitro-2, 3-dihydrobenzofuran as a tan solid., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2003/82787; (2003); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

23681-89-2, 2,3-Dihydrobenzofuran-6-ol is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a cooled (0 ¡ãC) solution of 2,3-dihydrobenzofuran-6-ol (0.52 g, 3.8 mmol) in anhydrous tetrahydrofuran (25 ml.) was added isopropylmagnesium chloride (2.1 ml_, 2 M solution in tetrahydrofuran, 4.2 mmol). The resultant suspension was stirred at 0 ¡ãC for 0.5 h and followed by the addition of 7-chloro-1-(diphenylmethyl)-1H-indole-2,3- dione (2.11 g, 15.5 mmol) in one portion. The reaction mixture was stirred at ambient temperature for 3 h and concentrated in vacuo. The crude product was purified by column chromatography with ethyl acetate in hexanes (0percent to 50percent gradient) to afford 7-chloro-1-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)- 1 ,3-dihydro-2H-indol-2-one (7.12 g, 95percent) as a colorless solid: 1H NMR (300 MHz, DMSO-CZ6) .pound.9.43 (s, 1 H), 7.56-7.18 (m, 13H), 6.99-6.86 (m, 2H), 6.60 (s, 1 H), 6.08 (s, 1H), 4.56 (t, J = 8.6 Hz, 2H), 3.10 (t, J = 8.6 Hz, 2H). C. Synthesis of 7-chloro-1 -(diphenylmethyl)-3-(6-hvdroxy-2,3-dihydro-1 – benzofuran-5-yl)-1,3-dihydro-2/-/-indol-2-one, 23681-89-2

As the paragraph descriping shows that 23681-89-2 is playing an increasingly important role.

Reference£º
Patent; XENON PHARMACEUTICALS, INC.; CHAFEEV, Mikhail; CHOWDHURY, Sultan; FRASER, Lauren; FU, Jianmin; LANGILLE, Jonathan; LIU, Shifeng; SUN, Jianyu; SUN, Shaoyi; SVIRIDOV, Serguei; WOOD, Mark; ZENOVA, Alla; JIA, Qi; CADIEUX, Jean-Jacques; GAUTHIER, Simon, J.; DOUGLAS, Amy Frances; HSIEH, Tom; CHAKKA, Nagasree; CIKOJEVIC, Zoran; WO2010/45251; (2010); A2;,
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.), 1-amino-3-azabicyclo[3.2.1]octane-2,4-dione (2.5 equiv.) in acetic acid is stirred at 120 ¡ãC overnight. The dark mixture is cooled andfiltered. The filter cake is dissolved in DCM and washed with saturated NaHCO3 and brine. The organic layer is dried (Na2504) and concentrated to provide 2-(2,4-dioxo-3- azabicyclo[3 .2.1 ]octan- 1 -yl)-4-fluoroisoindoline- 1,3 -dione.

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

Reference£º
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; HE, Minsheng; MICHAEL, Ryan, E.; (768 pag.)WO2017/197055; (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.24673-56-1,3-Methylbenzofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.

3-methylbenzofuran-2-carboxylic acid (0.4 mmol, 1 equiv), bis(4-cyanophenyl) diselenide (0.8 mmol, 2 equiv), Cu(OAc) 2 (0.06) at room temperature (mmol), 1,10-phenanthroline (0.06 mmol), potassium carbonate (1.2 mmol, 3 equiv) and 2 mL of toluene were added to the reaction tube, which was then filled with oxygen and replaced three times in an oxygen reaction environment at 150C. The reaction temperature was stirred for 24 h. By the end of the reaction was monitored by thin layer chromatography, the reaction mixture was cooled, filtered and then ethyl acetate was added, and then spin off the solvent, the product obtained was isolated by column chromatography (eluent: petroleum ether: diethyl ether = 98), the product is Yellow liquid, yield 77%, product weight 96 mg., 24673-56-1

The synthetic route of 24673-56-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wenzhou Medical University; Wu Ge; Wang Jing; (14 pag.)CN107188846; (2017); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem