Category: benzofuran

16859-59-9, 3-Hydroxyisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4: Alternative synthesis of Compound DE ED D(a) 2-Fluoro-5-[(E/Z)-(3-oxo-2-benzofuran- 1 (3H)-ylidene)methyl]benzonitrile (E) Sodium t-amylate (99.00 g, 0.854 mol) and 2-methyltetrahydrofuran (960 ml) were cooled to 2¡ãC under a nitrogen atmosphere. Diethyl phosphite (110 ml, 0.855 mol) was added dropwise maintaining the temperature at <5¡ãC. 2-Methyltetrahydrofuran (40 ml) was added as line wash. The reaction was stirred at 2¡ãC for 1 hour 40 minutes. A solution of 2-carboxybenzaldehyde (H)(80 g, 0.533 mol) in 2-methyltetrahydrofuran (200 ml) was added, maintaining the temperature at <7¡ãC throughout the addition. A line wash of 2-methyltetrahydrofuran (40 ml) was added. The reaction mixture was warmed to 200C and held at 200C for 20 minutes. Methanesulphonic acid (66 ml, 1.01 mol) was added over 1 hour and 10 minutes, followed by 2- methyltetrahydrofuran (40 ml). The reaction mixture was stirred at 20¡ãC over night. Methanesulphonic acid (7 ml, 0.101 mol) was added, followed by 2-methyltetrahydrofuran (7 ml) and the reaction stirred at 2O0C for a further 4 hours. Water (400 ml) was added at room temperature and the resulting biphasic mixture stirred at room temperature for 20 minutes. The lower aqueous layer was removed and a solution of potassium bicarbonate (53.50 g, 0.534 mol) in water (400 ml) was added to the organic layer. The biphasic mixture was stirred at room temperature for 20 minutes and then the lower aqueous solution was removed. The organic fraction was retained (solution of diethyl (3-oxo1 ,3-dihydro-2-benzofuran-1-yl)phosphonate). 16859-59-9, As the paragraph descriping shows that 16859-59-9 is playing an increasingly important role.

Reference£º
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2008/47082; (2008); A2;,
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10242-10-1, 5-Chlorobenzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Toa solution of (3S, 3aS) -3- (aminomethyl) -8- (3-oxomorpholino) -3, 3a, 4,5-tetrahydro-1H-benzo [b] oxazolo [3, 4-d] [1, 4] oxazepin-1-one (30 mg, 0.090mmol) and 5-chlorobenzofuran-2-carboxylic acid (20 mg, 0.10 mmol) indichloromethane (10 mL) were added 4-dimethylaminopyridine (28 mg, 0.23 mmol)and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (35 mg, 0.18mmol) . The mixture was reacted at rt for 10 hours. The reaction mixture wasconcentrated in vacuo to remove the solvent, and the residue was purified bysilica gel chromatography eluted with PE/EtOAc (V/V) 1/4 to give the titlecompound as a white solid (11 mg, 24) . The compound was characterized by thefollowing spectroscopic data: MS (ESI, pos. ion) m/z: 512.2 (M+1) and 1HNMR (400 MHz, CDCl3) : delta 7.68 (d, J 1.8 Hz, 1H) , 7.53 -7.40 (m,4H) , 7.15 (t, J 6.3 Hz, 1H) , 7.12 (d, J 2.3 Hz, 1H) , 7.02 (dd, J 8.6,2.4 Hz, 1H) , 4.55 -4.47 (m, 2H) , 4.33 (s, 2H) , 4.05 -4.00 (m, 2H) , 3.89 -3.69(m, 6H) , 2.35 -2.14 (m, 2H) ., 10242-10-1

10242-10-1 5-Chlorobenzofuran-2-carboxylic acid 937838, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Jiancun; ZUO, Yinglin; ZHANG, Yingjun; WANG, Xiaojun; ZHANG, Jin; WEN, Liang; CHENG, Guanjun; WO2015/110024; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10242-08-7,5-Methoxybenzofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 137 Preparation of 5-Methoxybenzofuran-2-carboxylic acid {(S)-1-[1-(2-cyano-benzenesulfonyl)-3-oxo-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide Following the procedure of Example 75, except substituting 2-cyanophenylsulfonyl chloride for thiazole-2-sulfonyl chloride and 5-methoxybenzofuran-2-carboxylic acid for benzofuran-2-carboxylic acid, the title compound was prepared. The residue was purified by HPLC. First eluding diastereomer; MS (M+H+): 581.4; 1H-NMR (400 MHz, CDCl3):. 8.15-8.13(d, 1H), 7.92-7.90(d, 1H), 7.81-7.74(m, 2H), 7.42-7.40(m, 2H), 7.08-7.03(m, 3H), 6.96(d, 1H), 5.10(m, 1H), 4.72-4.60 (m, 2H), 4.17 (d, 1H), 3.85(s, 3H), 3.75-3.70(d, 1H), 2.83-2.76(t, 1H), 2.27(m, 2H), 1.92-1.51(m, 5H), 1.02-1.01(m, 6); and the second eluding diastereomer: MS (M+H+) 581.2., 10242-08-7

10242-08-7 5-Methoxybenzofuran-2-carboxylic acid 288638, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; SmithKline Beecham Corporation; US2003/144175; (2003); A1;,
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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

Compound I (15.0 g) was added to 2N aqueous lithium hydroxide solution (105 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with 4N hydrochloric acid, and the resulting solid was filtered. The resultant was dried under reduced pressure to give Compound II (15.6 g).

64169-34-2, As the paragraph descriping shows that 64169-34-2 is playing an increasingly important role.

Reference£º
Patent; Dainippon Sumitomo Pharma Co., Ltd.; HORIUCHI, Yoshihiro; FUJIWARA, Hiroaki; SUDA, Hitoshi; SASAKI, Izumi; IWATA, Mitsutaka; SAWAMURA, Kiyoto; EP2612848; (2013); A1;,
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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;,
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799766-13-5, 7-Bromo-4-methylbenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,799766-13-5

A mixture of 4-methoxyphenylboronic acid (1.51 g, 9.95 mmol), Na2C03 (10.66 ml 2 N aqueous, 21.32 mmol), Pd (PPh3) 4 (0.411 g, 0.355 mmol), 7-bromo-4- methylbenzofuran (1.5 g, 7.11 mmol), and ethylene glycol dimethyl ether (75 ml) was heated to reflux overnight. The reaction was cooled, diluted with EtOAc and the layers separated. The organic layer was dried over anhydrous NA2S04, passed through a silica plug and concentrated. Column chromatography (10percent EtOAc/hexanes) afforded 1.59 g (94percent) product as a white waxy solid: mp 39-40 ¡ãC ; LH NMR (300 MHz, DMSO-d6) : 8 2. 51 (3H, s), 7.07 (2H, d, J = 8. 8 HZ), 7.08 (1H, d, J = 2. 3 HZ), 7.13 (1H, d, J = 7. 7 Hz), 7.37 (IH, d, J 7. 6HZ), 7.79 (2H, d, J = 8. 8 HZ), 8.04 (1H, d, J = 2. 2 HZ) ; MS (ESI) M/Z 239 ([M+H]+). Anal. for C16H1402 : Calc’d: C: 80. 65 H: 5.92 Found: C: 80. 89 H: 5.85

799766-13-5 7-Bromo-4-methylbenzofuran 21071800, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; WYETH; WO2004/103941; (2004); A2;,
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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

EXAMPLE 5 0.87 g. of a 55percent by weight sodium hydride dispersion in oil are washed under nitrogen three times with absolute tetrahydrofuran and subsequently covered with 8 ml. of absolute tetrahydrofuran. Thereafter, the mixture is cooled to 0¡ã C. and treated dropwise while stirring with a solution of 2.72 g. of 6-hydroxy-2,3-dihydrobenzofuran in 12 ml. of absolute tetrahydrofuran. The mixture is stirred for 1.5 hours at room temperature and again cooled to 0¡ã C. before a solution of 4.0 g. of 1,3,5-trimethylhexyl p-toluenesulfonate in 10 ml. of absolute tetrahydrofuran is added. Subsequently, the mixture is diluted with 10 ml. of absolute hexamethylphosphoric acid triamide and stirred for 24 hours at room temperature. The mixture is poured onto ice-water and extracted three times with diethyl ether. The extracts are washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/diethyl ether (98:2 parts by volume) there is obtained pure 6-[(1,3,5-trimethylhexyl)-oxy]-2,3 -dihydrobenzofuran which is distilled in a bulb-tube at 118¡ã C./0.3 mmHg; nD22 = 1.5057., 23681-89-2

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

Reference£º
Patent; Hoffmann-La Roche Inc.; US4002647; (1977); A;,
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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

A three-neck 5L round bottomed flask equipped with a stir bar, firestone valve, thermocouple, condenser and heating mantle was charged with tri-t-butyl phosphonium tetrafluoroborate (500 mg, 1.72 mmol), palladium (II) acetate (250 mg, 1.1 mmol) and 5-bromo-2-benzofuran-l(3H)- one (100 g, 469 mmol). DMF (1.88 L) was added to the flask, and the mixture was degassed three times by alternating vacuum and nitrogen purge. Commercially available bromo(l ,3- dioxolan-2-ylmelhyl)zinc solution (1.033 L, 516 mmol) was added via canula and the mixture was again degassed three times. The mixture was then heated at 85 0C for 5 h. Analysis by HPLC-MS indicated the reaction was not complete. The mixture was stirred at 85 0C for 5 more h. The mixture was then allowed to return to room temperature for overnight. 2-methylTHF (2L) and brine were added, and the mixture was stirred for 5 min. The layers were separated and the aqueous layer was extracted again with 2-methylTHF. The organic layers were combined, washed three times with brine (4L each), dried over MgSO4, filtered, and concentrated. The crude product was purified by flash chromatography (1.5 kg silica cartridge), eluting with 0-20% ethyl acetate in dichlromethane to afford 5-(l;3-dioxolan-2-ylmethyl)-2-benzofuran-l(3/i)-one. MS: m/z 221 (M+l)+., 64169-34-2

As the paragraph descriping shows that 64169-34-2 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP &amp;; DOHME CORP.; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; TEUMELSAN, Nardos, H.; YANG, Lihu; ZHU, Yuping; WALSH, Shawn, P.; WO2010/129379; (2010); A1;,
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Benzofuran | C8H6O – PubChem

127264-14-6, 5-(2-Bromoethyl)-2,3-dihydrobenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 13Preparation of (R)-3-((bis(3-fluorophenyl)methoxy)carbonylamin l-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-l-azoniabicyclo[2.2.2]octane bromide (compound 32)To a solution of (R)-bis(3-fluorophenyl)methyl quinuclidin-3- ylcarbamate (53 mg, 0.14 mmol, prepared as in example 1) in ethyl acetate (2 ml), 5-(2-bromoethyl)-2,3-dihydrobenzofuran (32.3 mg, 0.14 mmol) was added. The resulting mixture was stirred at room temperature for 8 days and then the solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=95/5) to collect (R)-3-((bis(3-fluorophenyl)- methoxy)carbonylamino)- l-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-l- azoniabicyclo[2.2.2]octane bromide (22.2 mg).1H NMR (300 MHz, DMSO-d6) delta ppm 8.08 (d, 1 H), 7.36 – 7.51 (m, 2H), 7.26 (d, 4 H), 7.06 – 7.19 (m, 3 H), 7.00 (d, 1 H), 6.64 – 6.81 (m, 2 H), 4.50 (t, 2 H), 3.92 – 4.13 (m, 1 H), 3.83 (t, 1 H), 3.37 – 3.59 (m, 4 H), 3.33 (d, 2 H), 3.19 – 3.25 (m, 1 H), 3.15 (t, 2 H), 2.90 (m, 2 H), 2.04 – 2.25 (m, 2 H), 1.68 – 2.04 (m, 3 H);LC-MS (ESI POS): 519.30 (M+)., 127264-14-6

As the paragraph descriping shows that 127264-14-6 is playing an increasingly important role.

Reference£º
Patent; CHIESI FARMACEUTICI S.p.A.; AMARI, Gabriele; RICCABONI, Mauro; DE ZANI, Daniele; WO2012/146515; (2012); A1;,
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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;,
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Benzofuran | C8H6O – PubChem