Heterocyclic Building Block-benzofuran

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 3; This example illustrates a process for preparing (S)-2-{1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide or a salt thereof wherein a substantially enantiomerically pure 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide or salt thereof, as determined by the inventive method, is used as an intermediate compound. In particular, this example illustrates that when using 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide having less than 0.2percent of the (R)-enantiomer as determined by the HPLC method of Example 1, the obtained (S)-darifenacin hydrobromide has less than 0.06percent of the (R)-enantiomer of darifenacin hydrobromide as determined by the HPLC method of Example 2.To a flask was added: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (54.15 g, 125.8 mmol, 99.63percent ee as determined by chiral HPLC method of Example 1), 5-(2-bromoethyl)-2,3-dihydrobenzofuran (34.86 g, 153.5 mmol), potassium hydroxide (20.78 g, 370.4 mmol), methyltriethylammonium chloride (2.810 g, 18.53 mmol), methylethylketone (170 mL) and water (34.0 mL). The reaction mixture was heated to reflux (approximately 75¡ã C.) and stirred for 6 hours, after which time the reaction mixture was cooled to 20-25¡ã C. After cooling, methylethylketone (96 mL) and water (106 mL) were added with stirring and the layers were separated. Ammonium chloride (106 mL, 10percent aqueous solution) was added to the organic layer with stirring and the layers were separated. The organic layer was evaporated to dryness and methylethylketone (106 mL) was added to the residue. The mixture was stirred until dissolution and hydrobromic acid (13 mL) was added, after which a precipitate formed. The resulting suspension was cooled to 0-5¡ã C. and stirred at this temperature for 2 hours. The suspension was filtered and the solid was washed with methylethylketone (2.x.20 mL). A solid was obtained (90.72 g, l.o.d.=41.51percent, 84.92percent yield, 95.68percent HPLC purity, 99.88percent ee as determined by chiral HPLC method of Example 2).

127264-14-6, The synthetic route of 127264-14-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Medichem, S.A.; US2008/312455; (2008); A1;,
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201809-69-0, 6-Bromobenzofuran-3(2H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To FA (14.6 g, 318 mmol, 3.5 equiv) cooled to 0 oC was added TEA (27.5 g, 272 mmol, 3.0 equiv) dropwise with stirring under nitrogen. To this mixture were added a solution of 6-bromo-2,3-dihydro-1-benzofuran-3-one (19.4 g, 90.9 mmol, 1.0 equiv) in DCM (500 mL) and (S,S)-N-(p-toluenesulfonyl)-1-2-diphenylethanediamine(chloro)(p- cymene)ruthenium(II) (1.65 g, 2.6 mmol, 0.03 equiv). The mixture was stirred overnight at room temperature and poured into water (500 mL). The resulting solution was extracted with DCM (500 mL) three times. The combined organic layers were washed with brine (500 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (EA/PE, 1/9) to afford 13.4 g (69%) of (3R)-6-bromo-2,3-dihydro- 1-benzofuran-3-ol as a yellow solid with 96% ee. (Chiral_SFC, CHIRALPAK AD-H 4.6*100 mm, 5 mum)., 201809-69-0

As the paragraph descriping shows that 201809-69-0 is playing an increasingly important role.

Reference£º
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; WANG, Wenyue; ASHCRAFT, Luke W.; (362 pag.)WO2019/144041; (2019); A1;,
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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.496-16-2,2,3-Dihydrobenzo[b]furan,as a common compound, the synthetic route is as follows.

Solid AlCl3 (5.55 g, 0.042 M) was added portionwise to a cold (00C) solution of dihydrobenzofuran (5.0 g, 0.042 M) arid ethyl oxalyl chloride (4.5 mL, 0.042 M) in dry dichloromethane (80 mL). After complete addition the dark solution was warmed up to RT and stirred for 2 hr. The resulting reaction mixture was slowly poured into a concentrated HCl/ice water solution (5 mL/200 mL). The aqueous mixture was stirred for 20 minutes and dichloromethane (1,50 mL) was added. Layers were separated. The aqueous layer was extracted with dichloromethane (1 x). The combined CH2CI2 extracts were dried over MgSO4, filtered, evaporated in vacuo and the crude oil purified by chromatography (Hexane/EtOAc) to provide the desired product as an oil (4.8 g) 54percent. 1H NMR (400 MHz, CDCl3) 87.88 (s, IH), 7.86 (d, J = 8.3 Hz, IH), 6.85 (d, J = 8.8 Hz, IH), 4.72 (t, J = 9 Hz, 2H), 4.45 (q, J = 7.2 Hz, 2H), 3.28 (t, J = 9.2 Hz, 2H), 1.42 (t, J = 7.2 Hz, 3H). MS (m/z): 221 (MH+).

496-16-2, 496-16-2 2,3-Dihydrobenzo[b]furan 10329, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/75567; (2007); A1;,
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Benzofuran | C8H6O – PubChem

54008-77-4, 2-Bromobenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

54008-77-4, General procedure: In a hot oven-dried Schlenk tube under N2 atmosphere were added Ph3Bi (0.25 mmol, 110 mg, 1.0 equiv), 2-bromobenzofuran (0.825 mmol, 163 mg, 3.3 equiv), Cs2CO3 (0.75 mmol, 244 mg, 3.0 equiv), Pd(OAc)2 (0.025 mmol, 5.6 mg, 0.1 equiv), PPh3 (0.1 mmol, 26 mg, 0.4 equiv), and NMP (3 mL) solvent. The resulting mixture was stirred in preheated oil bath at 90 C for 1 h. After the reaction is over, the mixture was cooled, quenched with dil HCl and extracted with ethyl acetate. The combined organic extract was washed with water, brine, and dried over MgSO4 and concentrated. The crude was subjected to silica gel column chromatography (230-400 mesh) using petroleum ether as the eluent to obtain the pure 2-phenylbenzofuran (2.1) as a white solid (140 mg, 96%). The product was characterized by spectroscopy and in comparison with the literature data.

54008-77-4 2-Bromobenzofuran 2776264, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Article; Rao, Maddali L.N.; Awasthi, Dheeraj K.; Talode, Jalindar B.; Tetrahedron Letters; vol. 53; 21; (2012); p. 2662 – 2666;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.89877-62-3,3-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile,as a common compound, the synthetic route is as follows.,89877-62-3

1-Oxo-1,3-dihydroisobenzofuran-6-carbonitrile (3.01 g, 18.9 mmol) obtained from Example 5-(2) was dissolved in a mixed solvent (200 ml) of tetrahydrofuran – methanol (3 : 1), and an aqueous solution of sodium hydroxide (1.004N; 17.4 ml, 17.4 mmol) was added thereto over a period of 10 minutes. The mixture was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. The resulting residue was dried using a vacuum pump. The obtained solid was dissolved in N,N-dimethylformamide (40 ml), and 4-methoxybenzyl chloride (2.96 g, 18.9 mmol) was added thereto. The mixture was heated at 70-80C for 1 hour. After cooling the mixture to 0C, dichloromethane (40 ml) was added thereto, and 4-(N,N-dimethylamino)pyridine (5.78 g, 47.3 mmol) and allyl chloroformate (4.56 g, 37.9 mmol) were added thereto, then the mixture was stirred at the same temperature for 30 minutes. The mixture was diluted with ethyl acetate and then washed successively with water and an aqueous solution of sodium chloride. The resulting mixture was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (100 g) column (eluent; hexane : ethyl acetate = 3 : 1) to afford the title compound (3.11 g, 43% yield) as a colorless oil. NMR spectrum (400 MHz, CDCl3) delta ppm: 3.83 (3H, s), 4.67 (2H, br d, J=6 Hz), 5.31 (2H, s), 5.31 (1H, d, J=10 Hz), 5.39 (1H, dd, J=17, 1 Hz), 5.66 (2H, s), 5.96 (1H, ddt, J=17, 10, 6 Hz), 6.93 (2H, d, J=9 Hz), 7.39 (2H, d, J=9 Hz), 7.70 (1H, d, J=8 Hz), 7.81 (1H, dd, J=8, 1 Hz), 8.30 (1H, d, J=1 Hz) IR spectrum nu max CHCl3 cm-1: 2236, 1725, 1296, 1256 Mass spectrum m/z (FAB): 381 (M+).

89877-62-3 3-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile 13289562, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Sankyo Company, Limited; EP1362856; (2003); 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.

To a solution of 3- methylbenzo[b]furan-2-carboxylic acid ( 1 eq, 52 mmol), methylamine hydrochloride (1.1 eq, 57.52 mmol), /V,/V-diisopropylethylamine (2.2 eq, 114.4 mmol), and HOBt (1.1 eq, 57.52 mmol) in DMF (150 mL) was added EDC (1.1 eq, 57.52 mmol). The reaction mixture was heated to 70 C overnight. The solvent was reduced to a few mL. The crude reaction mixture was diluted with CH2Cl2 and washed with saturated aqueous sodium bicarbonate. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure. Purification by flash column chromatography (4 Precursor a, 20:50:30, EtOAc:CH2Cl2:hexanes) yielded N, 3- dimethylbenzofuran-2-carboxamide (9.24 g, 48.9 mmol, 94%) as a white solid. 1H NMR (500 MHz, Chloroform-d): 57.61 (dt, J = 7.8, 1.0 Hz, 1H), 7.45 – 7.36 (m, 2H), 7.29 (ddd, J = 8.0, 6.4, 1.7 Hz, 1H), 6.64 (s, 1H), 3.03 (d, / = 5.0 Hz, 3H), 2.63 (s, 3H). 13C NMR (126 MHz, Chloroform-d): 5 161.10, 153.35, 142.96, 129.95, 127.04, 123.19, 122.19, 121.07, 111.55, 25.86, 9.00.

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; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; HERGENROTHER, Paul J.; GEDDES, Emily Jane; DROWN, Bryon Shane; MOTIKA, Stephen E.; PARKER, Erika Nicole; (141 pag.)WO2019/177975; (2019); A1;,
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Benzofuran | C8H6O – PubChem

87-41-2, Isobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Isobenzofuran-1(3H)-one (6.6 g, 49.6 mmol), NBS (9.7 g,54.5 mmol) and AIBN (0.8 g, 4.9 mmol) were diluted in dry carbon tetrachloride (CCl4) (200 mL) and heated to72C for 2.5h. The mixture was cooled to room temperatureovernight, filtered, and the residue was washed withpetroleum ether. The filtrate was concentrated in vacuo toprovide the crude product, which was recrystallized fromcyclohexane to give 2 (8.6 g, 81.8%) as a light brown solid;m. p. 79-82C (lit. [24]: 76-78C). – 1H NMR (600MHz,CDCl3): =7.65 (d, 1H, J=7.2Hz), 7.80-7.77 (m, 1H), 7.64-7.61(m, 2H), 7.41 (s, 1H). – 13C NMR (150MHz, CDCl3): =167.3,148.8, 135.2, 130.9, 125.9, 124.0, 123.5, 74.6.

87-41-2, 87-41-2 Isobenzofuran-1(3H)-one 6885, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Article; Fan, Lingling; Luo, Bilan; Luo, Zhongfu; Zhang, Li; Fan, Judi; Xue, Wei; Tang, Lei; Li, Yong; Zeitschrift fur Naturforschung, B: Chemical Sciences; (2019);,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6940-49-4,3-Bromophthalide,as a common compound, the synthetic route is as follows.

General procedure: Amine (1.05 Equiv) was added to Isatoic anhydride (1.0 Equiv) in water (4.0mL) and PEG400 (1.0mL) at RT and stirred for 1-2 hr. Upon completion of SM by TLC, added 3-bromoisobenzofuran-1(3H)-one (1.1 Equiv) and warm the reaction mixture to 90-95 C and maintained for 10-14 h. After completion of the reaction, cool the reaction mass up to 25-30 C and product was filtered and further purified via column chromatography through silica gel stationary phase and Ethyl acetate & Heptane mixture as eluent., 6940-49-4

As the paragraph descriping shows that 6940-49-4 is playing an increasingly important role.

Reference£º
Article; Madhubabu; Shankar; Reddy, G. Rajeshwar; Rao, T. Srinivasa; Basaveswara Rao, Mandava V.; Akula, Raghunadh; Tetrahedron Letters; vol. 57; 46; (2016); p. 5033 – 5037;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

54008-77-4, 2-Bromobenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

54008-77-4, General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

As the paragraph descriping shows that 54008-77-4 is playing an increasingly important role.

Reference£º
Article; Chelucci, Giorgio; Figus, Susanna; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 191 – 209;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

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.

5-bromobenzofuran (500 mg, 2.56 mmol) was dissolved in THF solution of isobutylzinc(H) bromide (0.5M, 15 mL, 7.40 mmol) in a microwave reaction tube. Pd(P1BUs)2 (65 mg, 0.128 mmol, 0.05 eqv.) was added to this solution. The mixture was purged with N2 gas for 3-5 min and heated at 100 0C for 30 min under microwave irradiation. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed with IN HCl aqueous solution, brine, filtered through Celite. The filtrate was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (ISCO system, 5percent EtOAc in hexanes) to give 0.331 g desired product (74percent yield): 1H NMR (400 MHz, CDCl3) delta 7.59 (s, IH), 7.35 (d, IH), 7.07 (d, IH), 6.70(s, IH), 2.59 (d, 2H)5 1.9 (m, IH), 0.9 (d, 6H).

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; PREDIX PHARMACEUTICALS HOLDINGS, INC.; WO2007/61458; (2007); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem