Heterocyclic Building Block-benzofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23145-07-5,5-Bromobenzofuran,as a common compound, the synthetic route is as follows.

General procedure: All reactions were prepared at the 1.0 mmol scale in a glovebox using an 8-mL screw cap vial with a Teflon-coated stir bar. The vial was charged with 4% Xantphos Pd G3 (0.038 g, 0.04 mmol), 7-methoxy-4-methylcoumarin (0.190g, 1mmol), and an aryl bromide (1.05 mmol). Next, 3 mL of a 1.0 M LiHMDS solution was added. Finally, 2 mL of THF was added to the reaction. The vial was capped, removed from the glovebox, and allowed to stir on an aluminum block preheated to 70 C for 24 hours. Upon completion, the reaction was allowed to cool. A standard workup was completed using about 2.5 mL of a 2.0 M HCl solution and dichloromethane to extract. Magnesium sulfate was utilized to dry the sample before gravity filtering and removing the solvent under reduced pressure. Completion was checked using TLC and GC-MS. The crude reaction mixture was loaded onto a silica gel column using a wet load technique. The yields reported are from one trial only., 23145-07-5

The synthetic route of 23145-07-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sexton, Mary E.; Okazaki, Ami; Yu, Zhuowen; van Venrooy, Alexis; Schmink, Jason R.; Malachowski, William P.; Tetrahedron Letters; vol. 60; 38; (2019);,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7169-34-8,Benzofuran-3(2H)-one,as a common compound, the synthetic route is as follows.

7169-34-8, General procedure: To a solution of benzofuran-3(2H)-one (1.0 mmol) and benzaldehyde(1.0 mmol) in dichloromethane (6 mL) was added aluminum oxide (30.0 mmol) at room temperature. After stirring for 6 h, the reaction mixture was filtered off. The filtrate was concentrated under vacuum and the residue was purified by flash chromatography on silica gel to give the desired compound

7169-34-8 Benzofuran-3(2H)-one 23556, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Article; Wang, Sheng; Xu, Lei; Lu, Yu-Ting; Liu, Yu-Fei; Han, Bing; Liu, Ting; Tang, Jie; Li, Jia; Wu, Jiangping; Li, Jing-Ya; Yu, Li-Fang; Yang, Fan; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 195 – 208;,
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4687-25-6, Benzofuran-3-carbaldehyde is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4687-25-6

General procedure: Using a previously described method,23 a catalytic amount of anhydrous ZnI2 (3.2 mg, 20 mumol) and trimethylsilyl cyanide (119 mg, 1.2 mmol) was added to a stirred solution of one of the aldehydes 1a-d (1 mmol) in dry dichloromethane (10 mL) and the resulting mixture was stirred at room temperature until all of the aldehydes was transformed. The solvent was evaporated and the crude product was redissolved in 10 mL of methanol. The formed trimethylsilyl cyanohydrin decomposed when HCl (3 M, 5 mL) was added. The reaction mass was evaporated to the final volume of 5 mL, after which water (5 mL) and dichloromethane (10 mL) were added. After the separation of the two layers, the aqueous layer was extracted with dichloromethane (2 .x. 10 mL). The combined organic layers were dried over anhydrous Na2SO4 and the solvent was evaporated in vacuo.

As the paragraph descriping shows that 4687-25-6 is playing an increasingly important role.

Reference£º
Article; Naghi, Mara Ana; Bencze, Laszlo Csaba; Brem, Juergen; Paizs, Csaba; Irimie, Florin Dan; Toa, Monica Ioana; Tetrahedron Asymmetry; vol. 23; 2; (2012); p. 181 – 187;,
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23145-07-5, 5-Bromobenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Isopropyl iodide (15.0 mmol) was added dropwise to a suspension of iodine (0.12 mmol), magnesium (30.0 mmol) in tetrahydrofuran (25 mL). After 15 min, a solution of 5-bromobenzofuran (15.2 mmol) in tetrahydrofuran (25 mL) was added dropwise and the reaction mixture was heated at reflux for 1 h. The mixture was cooled to -30 ¡ãC and sulfonyl chloride was bubbled through the reaction mixture for 10 min. The mixture was maintained for 30 min whereupon sulfuryl chloride (15.1 mmol) was added dropwise while cooling to -30 to -40 ¡ãC. The resulting solution was maintained for an additional 10 min and was allowed to warm to rt. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted with dichloromethane (150 mL), washed with brine (3 x 100 mL), dried (sodium sulfate), and concentrated. The residue was purified by Flash chromatography (100/1 to 50/1 petroleum ether/ethyl acetate) to provide benzofuran-5-sulfonyl chloride in 15percent yield as a white solid. Data: 1H NMR (CDCl3) delta 8.37 (s, 1H), 8.00 (d, 1H), 7.84 (s, 1H), 7.44 (d, 1H), 6.97 (s, 1H). LC/MS (ES) m/z 286 [M+BnH-l]+., 23145-07-5

The synthetic route of 23145-07-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2009/23844; (2009); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.37418-88-5,4-Hydroxyisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

7-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (1.55 g, 3.85 mmol) was cooled in an ice bath and then dissolved in a solution of 20 % trifluoroacetic acid/dichloromethane (15 ml). The reaction was stirred and allowed to slowly warm to ambient temperature during 3 hours. The solution was concentrated in vacuo to give crude 2-(1,4-dioxa-8-aza-spiro[4.5]dec-7-ylmethyl)isoindole-1,3-dione which was used directly in the following step (assumed 100 % yield). 1H-NMR (400 MHz, CDCl3): delta 9.26 (bs, 1H), 8.19 (bs, 1H), 7.78-7.75 (m, 2H), 7.74-7.71 (m, 2H), 4.11-3.98 (m, 5H), 3.90-3.79 (m, 3H), 3.26-3.17 (m, 1H), 2.10-2.00 (m, 3H), 1.92-1.88 (m, 1H). To a suspension of the above 2-(1,4-dioxa-8-aza-spiro[4.5]dec-7-ylmethyl)isoindole-1,3-dione (3.85 mmol) in absolute ethanol (25 ml) was added hydrazine (0.36 ml, 11.55 mmol). The reaction was stirred at 80 C (oil bath) for 6 hours, then cooled to ambient temperature and stirred for an additional 12 hours. The thick precipitate was filtered off and washed with ethanol. The filtrate was concentrated in vacuo and reconstituted in dichloromethane (20 ml), forming a small amount of a second precipitate, which was filtered off. The filtrate was evaporated in vacuo and the resulting oil was dissolved in water (10 ml) and basified with 1N sodium hydroxide until pH = 10. The aqueous layer was extracted with 20 % isopropyl alcohol/chloroform (12 x 40 ml). The combined organic extracts were dried (K2CO3), filtered and the solvent evaporated in vacuo affording 0.42 g (63 %) of (1,4-dioxa-8-aza-spiro[4.5]dec-7-yl)methylamine as an oil. 1H-NMR (300 MHz, CDCl3): delta 3.94 (bs, 4H), 3.11-3.05 (m, 1H), 2.81 (dt, 1H, J = 12 Hz and J = 3 Hz), 2.76-2.65 (m, 2H), 2.58-2.50 (m, 1H), 1.70-1.57 (m, 3H), 1.31 (t, 1H, J = 12 Hz). APCI-MS: m/z: 173.2 [M+H]+ To a solution of 4-hydroxy-isobenzofuran-1 ,3-dione (0.51 g, 3.09 mmol) in anhydrous N,N-dimethylformamide (7 ml) under nitrogen was added sodium hydride (130 mg, 3.25 mmol). Immediate evolution of gas and bright yellow color was observed. The mixture was stirred for 5 minutes after which benzyl bromide (1.8 ml, 15.45 mmol) was added. The reaction was stirred for 72 hours. Saturated sodium bicarbonate (2 ml) was added and the mixture stirred for 2 minutes, diluted in ethyl acetate (35 ml) and washed with saturated sodium bicarbonate (5 ml), 1N hydrochloric acid (5 ml), and brine (2 x 5 ml). The organic layer was dried (MgSO4), filtered and the solvent evaporated in vacuo. To the crude material was added hexane and the formed precipitate was filtered off, washed further with hexane and dried in vacuo to give 0.54 g (69 %) of 4-(benzyloxy)-isobenzofuran-1,3-dione as a solid. 1H-NMR (300 MHz, CDCl3): delta 7.74 (t, 1H, J = 8 Hz), 7.54 (d, 1H, J = 8 Hz), 7.47-7.29 (m, 6H), 5.36 (s, 2H). A solution of (1,4-dioxa-8-aza-spiro[4.5]dec-7-yl)methylamine (0.19 g, 1.1 mmol) and 4-(benzyloxy)-isobenzofuran-1,3-dione (0.27 g, 1.05 mmol) was prepared in a mixture of distilled dichloromethane (3 ml) and anhydrous N,N-dimethylformamide (2.5 ml) under nitrogen. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.23 g, 1.21 mmol) was added followed by triethylamine (0.46 ml, 3.3 mmol) and the reaction stirred at ambient temperature for 18 hours. The solution was concentrated in vacuo and the residue diluted with ethyl acetate (25 ml) and washed with water (5 ml), saturated sodium bicarbonate (5 ml), and brine (5 ml). The organic layer was evaporated in vacuo and the residue purified by silica gel chromatography using a mixture of 5 % methanol/dichloromethane/1 % triethylamine as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 0.22 g (50 %) of 4-benzyloxy-2-(1,4-dioxa-8-aza-spiro[4.5]dec-7-ylmethyl)-isoindole-1,3-dione as a semi-solid. 1H-NMR (400 MHz, CDCl3): delta 7.57 (t, 1H, J = 8 Hz), 7.48 (d, 2H, J = 7 Hz), 7.42-7.29 (m, 4H), 7.18 (d, 1H, J = 8 Hz), 5.31 (s, 2H), 3.94-3.90 (m, 4H), 3.65 (d, 2H, J = 6 Hz), 3.16-3.09 (m, 1H), 3.07-3.02 (m, 1H), 2.76 (dt, 1H, J = 13 Hz and J = 3 Hz), 1.78 (d, 1H, J = 12 Hz), 1.64-1.54 (m, 3H), 1.37 (t, 1H, J = 12 Hz), 1.08 (t, 1 H, J = 7 Hz). LC-MS: Rt=2.59 min, m/z: 409 [M+H]+ To a solution of the above 4-benzyloxy-2-(1,4-dioxa-8-aza-spiro[4.5]dec-7-ylmethyl)-isoindole-1,3-dione (0.22 g, 0.54 mmol) in 1,4-dioxane (4 ml) was added 4N hydrochloric acid (4 ml) and the reaction stirred in a 65 C (oil bath) for 6 hours. The mixture was basified with saturated sodium bicarbonate until pH = 8 and extracted with dichloromethane (3 x 20 ml). The combined organic extracts were dried (MgSO4), filtered, and the solvent evaporated in vacuo affording crude 4-benzyloxy-2-(4-oxo-piperidin-2-ylmethyl)-isoindole-1,3-dione as an oil. Which was used without further purification or characterization. The above crude 4-benzyloxy-2-(4-oxo-piperidin-2-ylmethyl)-isoindole-1,3-dione (0.17 g, 0.47 mmol) was dissolved in dichloromethane (4…, 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; Ontogen Corporation; EP1214324; (2006); B1;,
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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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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;,
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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;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

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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Benzofuran | C8H6O – PubChem

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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