Heterocyclic Building Block-benzofuran

271-89-6, Benzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of anisole 3A (3.0 mmol, 324.4 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol,1.55 M in hexane, 2.87 mL) at 0 C. The mixture was stirred for 2 h at 0 C under an argon atmosphere. Then, pivalonitrile (9.0 mmol, 748.2 mg) in THF (2.0 mL) was added to the mixture at 0 C and the obtained mixture was stirred for 30 min in the temperature range of 0 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 2-methoxybenzonitrile 2A (315.6 mg, 79%)., 271-89-6

The synthetic route of 271-89-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
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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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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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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 &; 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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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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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.496-41-3,Benzofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.,496-41-3

In a 50 mL round bottom flask equipped with a magnetic stirrer,Benzofuran-2-carboxylic acid (162 mg, 1.0 mmol, 1.0 eq),Selectfluor (708 mg, 2.0 mmol, 2.0 eq), potassium fluoride(232 mg, 4.0 mmol, 4.0 eq); then dichloroethane (3.3 mL) and water (1.7 mL) were added as solvent;The reaction bottle was sealed in an oil bath at 70 C and heated and stirred for 15 hours. After the reaction was completed,The reaction mixture was extracted twice with 20 mL of ether. The organic phase was combined and washed with saturated brine and then dried over anhydrous sodium sulfate. After drying,Solvent to give the crude product; the crude product was subjected to column separation using analytically pure n-pentane as eluent to give the final productThe 2-fluorobenzofuran was a yellow oily liquid in 75% yield.

As the paragraph descriping shows that 496-41-3 is playing an increasingly important role.

Reference£º
Patent; Central South University; Tang, Zhenyu; Yuan, Xi; Yao, Jianfei; (24 pag.)CN106397377; (2017); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.41019-56-1,Methyl benzofuran-4-carboxylate,as a common compound, the synthetic route is as follows.

A solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) wasadded to a solution of the above ester (2.02 g, 11.4 mmol) in THF(20 mL) and MeOH (20 mL) and the solution was stirred at 20 Cfor 16 h and then evaporated. The residue was dissolved in water(50 mL) and acidified with conc. HCl and the precipitate was filteredand dried to give benzofuran-4-carboxylic acid (1.83 g,99%). 1H NMR (DMSO d6) d 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H),7.85-7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz,1H). Found: [MH] = 161.1.

41019-56-1, The synthetic route of 41019-56-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1797 – 1809;,
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10242-11-2, 5-Bromobenzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 10 To a 100ml flask was added with 5-bromo-2-carboxybenzofuran (4.82g, 0.02mol), piperazine (3.44g, 0.04mol), copper chloride (0.27g, 0.002mol), and dimethyl sulfoxide (50ml), and was heated with stirring at 150 C reaction. The reaction was monitored by thin layer chromatography, after the end of the reaction,The solvent was removed, 10ml of diethyl ether was added to the system, with vigorous stirring, to precipitate a solid.The solid was recrystallized from ethyl acetate to give 5-piperazin-2-carboxybenzofuran 3.34g, 68% yield., 10242-11-2

As the paragraph descriping shows that 10242-11-2 is playing an increasingly important role.

Reference£º
Patent; Shaanxi Buchang Hi-Tech Pharmaceutical Co., Ltd; Zhao, Buzhang; Zhao, Chao; (9 pag.)CN103467422; (2016); B;,
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35700-40-4, 2,3-Dihydrobenzofuran-7-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Following the general procedure of acid-amine coupling as shown in Example 23, Compound 8(25 mg, 0.033 mmol) was treated with 2,3-dihydro-benzofuran-7-carboxylic acid (7.4 mg, 0.045 mmol), DIEA (0.0163 mL, 0.094 mmol) and the coupling reagent PyAop (29.3 mg, 0.056 mmol) in acetonitrile (3 mL). After purification by Prep.HPLC column, a white solid was obtained as final 1:1 diastereomers (Compound 30) (18 mg, 70% yield). (Compound 30, 48110-188D): LC-MS (retention time: 1.547 minutes.), MS m/z 684(MH+)., 35700-40-4

As the paragraph descriping shows that 35700-40-4 is playing an increasingly important role.

Reference£º
Patent; Hewawasam, Piyasena; Ding, Min; Sun, Li-Qiang; Scola, Paul Michael; US2007/10455; (2007); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.

69999-16-2, PREPARATION 12 Preparation of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran STR33 A solution of (2,3-dihydrobenzofuran-5-yl)acetic acid (4.9 g–see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H N.m.r. (CHCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm.

The synthetic route of 69999-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc.; US5096890; (1992); A;,
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