Heterocyclic Building Block-benzofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10035-16-2,Benzofuran-5-carbaldehyde,as a common compound, the synthetic route is as follows.

To a solution of aldehyde (400 g) in ether (10 ml) was added LiN(TMS)2 (1 M in THF, 3.3 ml) at 0 C. dropwise. The solution was stirred at 0 C. for 30 min and EtMgBr (3M in THF, 1.83 ml) was added dropwise. The reaction was refluxed overnight, cooed to 0 C., quenched with saturated ammonium chloride and extracted with ether. The ether was stirred with 3N HCl (20 ml), then the aqueous layer was basified with NaOH pellets and extracted with ether. The ether layer was washed with brine, dried with MgSO4, filtered and concentrated in vacuo to give 220 mg of product (46%).

The synthetic route of 10035-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schering Corporation; US2004/106794; (2004); 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.196799-45-8,2,3-Dihydrobenzofuran-7-carbaldehyde,as a common compound, the synthetic route is as follows.

General procedure: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products.

As the paragraph descriping shows that 196799-45-8 is playing an increasingly important role.

Reference£º
Article; Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Braeuner-Osborne, Hans; Kristensen, Jesper Langgaard; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3933 – 3937;,
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Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.569-31-3,6,7-Dimethoxy-3H-1-isobenzofuranone,as a common compound, the synthetic route is as follows.

A solution of Compound 31a (6.31 g, 32.5 mmol) in acetonitrile (60 mL) was added NCS (4.77 g, 35.7 mmol) . After stirring at 60 C for 1 hour, the insoluble matter was collected by filtration, so as to yield compound 31b. Yield: 6.15 g, (83%) 1H-N R (CDC13) delta: 3.91 (3H,’s), 4.09 (3H, s) , 5.15 (2H, s), 7.16 (1H, s) .

As the paragraph descriping shows that 569-31-3 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; SHIONOGI & CO., LTD.; LIAO, Xiangmin; PEARSON, Neil, David; PENDRAK, Israil; THALGI, Reema; YAMAWAKI, Kenji; YOKOO, Katsuki; SATO, Jun; KUSANO, Hiroki; AOKI, Toshiaki; WO2014/68388; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3199-61-9,Ethyl benzofuran-2-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of ethyl benzofuran-2-carboxylate 1 (3.80g, 20mmol), and hydrazine monohydrate (3mL, 61.5mmol) in EtOH (5mL) was refluxed for 3h. After cooling the formed precipitate was filtered off, washed with water (5¡Á10mL) dried and used without further purification. Yield 85%. Mp 190-192C (lit. 190-194C [47]). 1H NMR (DMSO-d6): delta 4.56 (s, 2H, NH2), 7.31 (m, 1H, Ar), 7.42 (m, 1H, Ar), 7.50 (s, 1H, Ar), 7.63 (d, J=8.5Hz, 1H, Ar), 7.74 (d, J=8.0Hz, 1H, Ar), 10.00 (s, 1H, NH). IR (Nujol) 3322, 3184, 1661, 1601cm-1m/z 177 (M+H)+. Anal. Calcd for C9H8N2O2: C, 61.36; H, 4.58; N, 15.90. Found: C, 61.29; H, 4.59; N, 15.93.

As the paragraph descriping shows that 3199-61-9 is playing an increasingly important role.

Reference£º
Article; Baldisserotto, Anna; Demurtas, Monica; Lampronti, Ilaria; Moi, Davide; Balboni, Gianfranco; Vertuani, Silvia; Manfredini, Stefano; Onnis, Valentina; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 118 – 125;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13391-28-1,5-Methoxybenzofuran,as a common compound, the synthetic route is as follows.

Step A: Preparation of 5-Methoxy-2-sulfamoylbenzo[b]furan A solution of 5-methoxybenzo[b]furan (10.8 g, 73 mmol) in 100 ml of dry THF was cooled to -65 C. A 1.6M solution of n-butyllithium in hexane (50 ml, 80 mmol) was added rapidly, dropwise, such that the temperature did not exceed -55 C. After 15 minutes at -55 C. sulfur dioxide gas was passed into the reaction flask until an aliquot removed from the flask and dissolved in water was no longer basic to pH paper. Hexane (100 ml) was added to precipitate the product. After warming to room temperature, the product was isolated by filtration. The crude product was dried under low vacuum for 18 hours at room temperature, yielding 15.6 g (98%) of a tan powder. The dry sulfinate salt so obtained was suspended in 150 ml CH2 Cl2 and cooled to 5 C. prior to adding 10.7 g of N-chlorosuccinimide (80 mmol). Stirring was continued for 15 minutes at 5 C. and the cooling bath was removed. After an additional 15 minutes the suspension was filtered through a pad of filter aid. Evaporation of the solvent furnished 17.2 g of sulfonyl chloride as a brown solid. This material was dissolved in 50 ml of dry acetone and added over a 1 minute period to a chilled (5 C.) stirring solution of 15 ml NH4 OH in 150 ml acetone. After 30 minutes the solvent was evaporated. The residue was partitioned between water and ethyl acetate. The organic phase was washed with brine and dried (Na2 SO4). Evaporation left 17.2 g of brown solid. The pure compound was obtained by recrystallization from dichloroethane; m.p. 119-120 C. Analysis calculated for C9 H9 NO4 S: C, 47.57; N, 6.16; H, 3.99; Found: C, 47.52; N, 6.14; H, 4.02. ‘H NMR (d6 -acetone) 7:7.50 (1H, d, J=9), 7.30 (1H, s), 7.25 (1H, d, J=3), 7.1 (1H, dd, J=9, 3), 3.83 (3H, s).

As the paragraph descriping shows that 13391-28-1 is playing an increasingly important role.

Reference£º
Patent; Merck & Co., Inc.; US4544667; (1985); A;,
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77095-51-3, Benzofuran-6-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

g) A mixture of 0.25 mmol of compound 1.11 and 0.26 mmol of HATU in 1 mmol of DIEA and 2 mL of DMF was stirred at room temperature for 30 min, followed by adding a solution of 0.22 mmol of compound 1.5 in 1 mL of DMF. The resulting mixture was stirred 45C for 12 hours. The solvent was removed, and the residue was purified to give compound 1. 6 in 50-65% yield. Subsequently, compound 1.6 was hydrolyzed with LiOH (1.0 M aqueous, 0.5 mL) in THF (3 mL) for 2 hours. The rexaction mixture was then acidified with HCl (aqueous), extracted with ethyl acetate (50 mL), dried over anhydrous magnesium sulfate and concentrated to give compound 1 in quantitative yield NMR (400 MHz, CD3OD) : 8 7.91 (s, 1H), 7.75 (d, J= 8.0 Hz, 1H), 7.67 (s, 3H), 7.36 (d, J= 8. 0 HZ, 1H), 7.13 (s, 1H), 6.96 (s, 1H), 5.01 (t, J= 6.8 Hz, 1H), 4.68 and 4.89 (m, 2H), 3.85 (d, J= 6. 8 Hz, 2H), 3.70 and 4.02 (m, 2H), 2.93 (m, 2H) ppm; ESI-MS (m/z) : (milz 586.10.

As the paragraph descriping shows that 77095-51-3 is playing an increasingly important role.

Reference£º
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2005/44817; (2005); 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.16859-59-9,3-Hydroxyisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

General procedure: 2-Formylbenzoic acid (1a; 1.0 equiv) and DMAP (0.1 equiv) were dis-solved in CH2Cl2 (0.15 M), producing a colorless clear solution. Thedesired carboxylic anhydride (2.0 equiv) and triethylamine (1.0equiv) were subsequently added and the reaction mixture was stirredat r.t. until complete conversion of the starting material was achieved(monitored by TLC). The solvent was removed under reduced pres-sure and the crude products were purified by column chromatogra-phy (n-hexane/EtOAc, 2:1).

As the paragraph descriping shows that 16859-59-9 is playing an increasingly important role.

Reference£º
Article; Niedek, Dominik; Schuler, Soeren M.M.; Eschmann, Christian; Wende, Raffael C.; Seitz, Alexander; Keul, Felix; Schreiner, Peter R.; Synthesis; vol. 49; 2; (2017); p. 371 – 382;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.128851-73-0,6-Bromobenzofuran,as a common compound, the synthetic route is as follows.

General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiI2 (3.1 mg, 0.01mmol, 5 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrerbar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA (60 muL, 2 equiv.)and N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) were subsequently added in this order. The solution was gently bubbled with ethylene balloon for approximately 30 seconds. The solution was then taken up into a 8 mL stainless steel syringe pre-purged with argon, and quickly assembled onto thestop-flow micro tubing, SFMT setup. Solution was pumped into the SFMT at 400 muL/min while maintaining approximately 1:1 gas-liquid slug flow at 250 PSI. Filled SFMT was then irradiated with blueLED (2 meter strip, 18 W) in a 100oC oil bath for 24 hours. The SFMT was wash with DCM (8 mL) and subjected to GC analysis (Figure S5). Then water (30 mL) was added to reaction mixture and extracted with DCM (10 mL) three times. Combined organic layer was successively wash with brine three timesand dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography to yield the product as a mixture of meso/dl isomers (which could not be separated by column chromatography).

As the paragraph descriping shows that 128851-73-0 is playing an increasingly important role.

Reference£º
Article; Li, Jiesheng; Luo, Yixin; Cheo, Han Wen; Lan, Yu; Wu, Jie; Chem; vol. 5; 1; (2019); p. 192 – 203;,
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Benzofuran | C8H6O – PubChem

610-93-5, 6-Nitroisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of compounds 12 (10 mmol) and 10% (mass fraction) Pd/C (0.20 g) in MeOH (20 mL) was subjected to standard hydrogenolysis condition at atmospheric pressure (balloon) and room temperature. The progress of the reaction was monitored by TLC. After completion of the reactions, the reaction mixture was filtered off and the filtrate was evaporated on a rotary evaporator to afford the crude products 13, which were used directly in the next step without further purification. Yield: 87%, Mp: 186-187 C. 1H-NMR (CDCl3, 600 MHz), d: 7.28(s, 1H, ArH), 7.11-7.07(m, 1H, ArH), 7.05(dd, J = 8.1Hz, 2.1Hz, 1H, ArH), 5.25(s, 2H), 3.95(s, 2H, NH2). 5110 X. Hu et al. 123

The synthetic route of 610-93-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hu, Xia-min; Cui, Zhi-wen; Dong, Wei; Zhu, Yue; Gao, Cheng-zhi; Xu, Shi-qiang; Yuan, Qiong; Yu, Zhi-jun; Min, Zhen-li; Research on Chemical Intermediates; vol. 44; 9; (2018); p. 5107 – 5122;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

69604-00-8, Ethyl 5-nitrobenzofuran-2-carboxylate is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

20.0g of ethyl 5-nitrobenzofuran-2-carboxylate prepared in Example 2 was added into a reaction flask, 300ml of ethanol was added, 2g of 5% Pd on carbon was added, the mixture was replaced with hydrogen twice, and the hydrogen pressure was controlled to 0.3 -0.5MPa, 10-30 hydrogenation reaction for 3 hours, the reaction was completed, filtered and the filtrate was concentrated under reduced pressure to give dry 5-aminobenzofuran-2-carboxylic acid ethyl ester 17.1g, yield 98%.

The synthetic route of 69604-00-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; (8 pag.)CN107674052; (2018); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem