Heterocyclic Building Block-benzofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.700-85-6,5-Fluoroisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

A mixture of5-fluoro-3H-isobenzofuran-1-one (1 g, 6.6 mmol, 1 eq), N-bromosuccinimide (1.2 g,6.8 mmol, 1.03 eq) and dibenzoyl peroxide (111 mg, 0.5 mmol, 0.07 eq) in CCw is stirred at 80C for 1.5h. The precipitated is filtered and the filtrate is concentrated. The residue is partitioned between DCM andwater. The two layers are separated and the aqueous layer is extracted with DCM. The combined organiclayers are dried (filtered through phase separator) and concentrated to afford the desired product.

700-85-6 5-Fluoroisobenzofuran-1(3H)-one 13770566, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; GALAPAGOS NV; MAMMOLITI, Oscar; JANSEN, Koen, Karel; MENET, Christel, Jeanne, Marie; PALISSE, Adeline, Marie, Elise; TRICARICO, Giovanni, Alessandro; EL BKASSINY, Sandy; JAUNET, Alexis, Patrick, Claude; ALLART, Brigitte; DUTHION, Beranger; BREBION, Franck Laurent; (324 pag.)WO2019/7696; (2019); A1;,
Benzofuran – Wikipedia
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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.

To 5-methoxybenzofuran (188 mg, 1.269 mmol) in THF (4.0 mL) at -78 C wasadded 1.6 N n-BuLi in hexanes (1.190 mL, 1.903 mmol) dropwise. The solution became slightly yellow. The reaction mixture was stirred at -78 C for 20 mm, followed by addition of triisopropyl borate (0.737 mL, 3.17 mmol). After 30 mm stirring at -78 C, the cooling bath was removed and the stirring was continued at room temperature for 1.5h. The reaction mixture was diluted with EtOAc, quenched with 3.0 mL of 1.0 N HC1.After stirring at room temperature for 25 mm, the organic layer was collected, washedwith brine and dried over sodium sulfate. After evaporation of solvent, the cmde product was dissolved in a small amount of chloroform/a drop of MeOH and charged to a 4 g silica gel cartridge which was eluted with hexanes for 2 mm., then a 10 mm gradient from 0% to 60%. The desired fractions were combined, concentrated and lyophilized to giveIntermediate 2A (170 mg, 0.886 mmol, 69.8 % yield) as a white solid. ?H NMR (500MHz, methanol-d4) oe 7.41 (d, J=9. 1 Hz, 1H), 7.30 (s, 1H), 7.14 (d, J2.5 Hz, 1H), 6.96 (dd, J=8.9, 2.6 Hz, 1H), 3.84 (s, 3H); LC-MS: method A, RT = 1.45 mm, MS (ESI) m/z: 149.0 (M-B(OH)2)t

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); 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.15832-09-4,6-Methoxy-3(2H)-benzofuranone,as a common compound, the synthetic route is as follows.

To a solution of 6-methoxybenzofuran-3(2H)-one (58?mg, 0.354?mmol) in MeOH (5?mL) were added an aqueous solution of KOH (50%, 0.30?mL) and 3,4-dimethoxybenzaldehyde (59?mg, 0.354?mmol), and the mixture was stirred at room temperature for 2?h. The solid was then filtered, washed with cold MeOH and dried. The crude product was recrystallized from MeOH to afford 34 (25?mg, 23%) as a yellow solid. 1H NMR (CDCl3) delta 7.72 (d, 1H, J?=?8.3?Hz), 7.51 (d, 1H, J?=?1.9?Hz), 7.48 (dd, 1H, J1?=?8.3?Hz, J2?=?1.9?Hz), 6.94 (d, 1H, J?=?8.3?Hz), 6.80 (s, 1H), 6.77 (dd, 1H, J1?=?8.3?Hz, J2?=?2.1?Hz), 6.76 (s, 1H), 3.99 (s, 3H), 3.95 (s, 3H), 3.94 (s, 3H). 13C NMR (CDCl3) delta 183.0, 168.4, 167.4, 150.8, 149.2, 147.0, 126.0, 125.9, 125.6, 115.3, 113.9, 112.6, 112.2, 111.4, 96.8, 56.3, 56.2, 56.2. IR (ATR) upsilon 1596, 1516, 1442, 1424, 1292, 1283, 1261, 1169, 1145, 1122, 1091, 1043, 1015, 949, 896, 862, 835, 816, 771, 700?cm-1. HRMS (ESI) calc. for C18H17O5 [M + H]+ 313.1071, found 313.1065.

15832-09-4 6-Methoxy-3(2H)-benzofuranone 585368, abenzofuran compound, is more and more widely used in various.

Reference£º
Article; Olleik, Hamza; Yahiaoui, Samir; Roulier, Brayan; Courvoisier-Dezord, Elise; Perrier, Josette; Peres, Basile; Hijazi, Akram; Baydoun, Elias; Raymond, Josette; Boumendjel, Ahcene; Maresca, Marc; Haudecoeur, Romain; European Journal of Medicinal Chemistry; vol. 165; (2019); p. 133 – 141;,
Benzofuran – Wikipedia
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.

Example 5; Preparation of 5-(2,3-dihydrobenzofuran-5-yl)-3-(3-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy)benzyl)-5-methylimidazolidine-2,4-dione; 5-a) Preparation of 5-(2,3-dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dione; 2,3-Dihydrobenzofuran (10 g, 83.2 mmol) was dissolved in dichloromethane (400 mL). The resultant mixture was added sequentially with acetyl chloride (11.8 mL, 167 mmol) and aluminum chloride (33.3 g, 250 mmol) at -10 C., and stirred at -10 C. for 0.5 hour. The reaction solution was added with 5% aqueous solution of hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. 1-(2,3-Dihydrobenzofuran-5-yl)ethanone (13.4 g, yield 99%) was obtained as a colorless oil.1H-NMR (CDCl3) delta: 2.55 (3H, s), 3.25 (2H, t, J=8.6 Hz), 4.67 (2H, t, J=8.6 Hz), 6.80 (1H, d, J=8.1 Hz), 7.80 (1H, dd, J=1.9, 8.1 Hz), 7.85 (1H, d, J=1.9 Hz).

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KOWA COMPANY, LTD.; US2010/48610; (2010); 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.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.

Step 3. 2~(2,3-dihydro-l~benzofuran-5-ylmethyl)-l-(3-rnethylbutyl)-N,N-bis(2,2,2-trifluoro- ethyI)-lH-benzimidazole-5-carboxamide[0168] To a mixture of 3-amino-4-[(3-methylbutyl)amino]-N,N-bis(2,2,2- trifluoroethyl)benzamide (Step 2 of the Example 1, 0.175g, 0.454 mmol, lequiv), 2,3-dihydro-l- benzofuran-5-ylacetic acid (0.089g, 0.50 mmol, 1.1 equiv) and HATU (0.19Og, 0.500 mmol, 1.1 equpsiloniv) was added a solution of DIPEA (160 muL, 0.92 mmol, 2equiv) in DMF (5 mL). The mixture was stirred overnight at room temperature. Complete consumption of the starting material was confirmed by LC-MS. DMF was removed under reduced pressure. Ethyl acetate was added to the resulting residue. The organic layer was washed once with a saturated aqueous <n=”54″/>NaHCtheta3 solution, once with brine and dried over anhydrous Na2SO4. Ethyl acetate was removed under reduce pressure. The resulting residue was dissolved in dichloroethane and a few drops of concentrated HCl were added. The mixture was stirred at 80 C for 3 hours. Complete consumption of the starting material was confirmed by LC-MS. Dichloromethane was added. The organic layer was washed once with a 2M aqueous NaOH solution, once with brine and dried over anhydrous Na2SO4. Dichloromethane was removed under reduced pressure. The resulting residue was purified by column chromatography on silica gel (hexanes/EtOAc, 50:50) to afford 2-(2,3-dmydro-l-benzofuran-5-ylmethyl)-l-(3-methylbutyl)-N,N-bis(2,2,2-trifluoro- ethyl)-lH-benzimidazole-5-carbochiamide (0.173 mg) in 72% yield. The product was dissolved in methanol (about 5 mL) and 1 equivalent of TFA was added. The mixture was stirred at room temperature for about 30 minutes. Methanol was removed under reduced pressure. Water was added and the resulting residue was lyophilized to afford 2-(2,3-dihydro-l-benzofuran-5- ymiethyl)-l-(3-me1hylbu1yl)-N,N-bis(2,2,2-trifluoro-e&yl)-lH-benzimidazole-5-carboxamide as the corresponding TFA salt. 1H NMR (400 MHz, METHANOL-D4) 6 ppm 0.96 (d, /=6.64 Hz, 6 H) 1.45 – 1.54 (m, 2 H) 1.63 – 1.75 (m, 1 H) 3.18 (t, /=8.79 Hz, 2 H) 4.32 – 4.44 (m, 6 H) 4.49 (s, 2 H) 4.54 (t, J=8.79 Hz, 2 H) 6.75 (d; /=8.20 Hz, 1 H) 7.07 (dd, J=8.20, 1.95 Hz, 1 H) 7.20 (s, 1 H) 7.58 (dd, /=8.50, 1.46 Hz, 1 H) 7.79 (d, /=0.78 Hz, 1 H) 7.87 (d, /=8.59 Hz, 1 H); MS (ESI) m/z 527.8 (MHhH)+; Anal. Calcd (%) for C26H27F6N3O2 + 1.0 TFA: C, 52.42; H, 4.40; N, 6.55. Found: C, 52.52; H, 4.27; N 6.18.

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; WO2007/91950; (2007); 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.18761-31-4,5-Nitrobenzofuran,as a common compound, the synthetic route is as follows.

EXAMPLE 33 N-(4-methylfuro[2,3-g]quinazolin-2-yl)guanidine was made in the same manner as N-(6,7-dibutoxy-4-methyl-2-quinazolinyl)guanidine (see Example 1) except that 5-nitro-[2,3]-benzofuran was used in place of 1,2-dibutoxy-4-nitrobenzene. Name: 6,6,8-trimethyl-5,6-dihydrofuro[2,3-g]quinoline (synthesised using Method B (70% yield)). Data: 1H NMR (CDCl3) delta 7.53 (br s, 1H), 7.21 (dd, 1H, J=8.4, 0.6 Hz), 6.94 (br s, 1H), 6.51 (d, 1H, J=8.4 Hz), 5.38 (d, 1H, J=1.2 Hz), 2.29 (d, 3H, J=1.2 Hz), 1.29 (s, 6H).

The synthetic route of 18761-31-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Forray, Carlos C.; Kawakami, Joel; Konkel, Michael J.; Boteju, Lakmal W.; Wetzel, John M.; Noble, Stewart A.; Wan, Honghe; US2003/176314; (2003); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

95333-17-8, Benzofuran-4-carbonitrile is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a single-necked flask, add benzofuran-4-carbonitrile C1-1e (300 mg, 2.09 mmol), methanol (50 mL), nickel chloride (543 mg, 4.19 mmol), and slowly add sodium borohydride (159 mg, 4.19 mmol). , 2 hours reaction at room temperature.The mixture was filtered through celite, washed with methanol,The filtrate was concentrated under reduced pressure to obtain a crude product. The crude was purified on silica gel (dichloromethane:Methanol = 10: 1) to give benzofuran-4-ylmethylamine C2-1 (50 mg, 16.2% yield) as a yellow solid.

#N/A

Reference£º
Patent; Shanghai Qingyu Pharmaceutical Technology Co., Ltd.; Zou Bin; Ma Shichao; Wang Xiang; Zhang Zhongguo; (92 pag.)CN110563722; (2019); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17403-47-3,5-Nitro-2,3-dihydrobenzofuran,as a common compound, the synthetic route is as follows.

General procedure: Procedure B: The nitro-group containing compound was dissolved in MeOH (or a mixture of MeOH and tetrahydrofuran) and then 10% Pd/C was added. The mixture was stirred at room temperature under hydrogen gas until the starting material had been consumed. The crude mixture was filtered through Celite, washed with methanol, and then concentrated. The product was carried on to the next step without further purification or was purified by column chromatography.

The synthetic route of 17403-47-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Lee, Jeewoo; Tran, Phuong-Thao; Hoang, Van-Hai; Thorat, Shivaji A.; Kim, Sung Eun; Ann, Jihyae; Chang, Yu Jin; Nam, Dong Woo; Song, Hyundong; Mook-Jung, Inhee; Lee, Jiyoun; Bioorganic and Medicinal Chemistry; vol. 21; 13; (2013); p. 3821 – 3830;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23681-89-2,2,3-Dihydrobenzofuran-6-ol,as a common compound, the synthetic route is as follows.

EXAMPLE 25 875 mg. of a 55percent by weight sodium hydride dispersion in oil are washed three times with absolute tetrahydrofuran and then covered with 10 ml. of absolute tetrahydrofuran. Thereafter, the mixture is treated at 0¡ã C. and 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 one hour (during which time it is allowed to warm up to room temperature), then again cooled to 0¡ã C. and added dropwise to a solution of 1-bromo-7-ethoxy-3,7-dimethyl-2-octene in 12 ml. of absolute tetrahydrofuran. 12 ml. of pure hexamethylphosphoric acid triamide are then added to the mixture, the ice bath is removed and the mixture stirred for 3 hours. The mixture is worked up by pouring it onto ice-water and extracting the resulting mixture 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 (19:1 parts by volume) there is obtained pure 6-[(7-ethoxy-3,7-dimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran which is distilled in a bulb-tube at 150¡ã C./0.05 mmHg; nD20.5 = 1.5172.

23681-89-2 2,3-Dihydrobenzofuran-6-ol 12236540, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; Hoffmann-La Roche Inc.; US4002647; (1977); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59434-19-4,4-Aminophthalide,as a common compound, the synthetic route is as follows.

Example 139A(?)-6-Fluoro-4-((l -methyl- lH-imidazol-2-yl)methyleneamino)isobenzofuran- 1 (3H)-one[00798] A solution of 1 -methyl- lH-imidazole-2-carbaldehyde (659 mg, 6.0 mmol), 4-amino-6- fluoroisobenzofuran- 1 (3H)-one (1.0 g, 6.0 mmol), and anhydrous magnesium sulfate (7.2 g, 60.0 mmol) in acetonitrile (100 mL) was heated to reflux for 2 days. The solution was filtered and the solvents were removed in vacuum. The crude product was re-crystallized from isopropanol to afford the title compound (1.068 g, yield 68%) LC-MS (ESI) m/z: 260 (M+l)+. ?-NMR (400 MHz, DMSO-d6) delta (ppm): 4.04 (s, 3H), 5.49 (s, 2H), 7.24 (s, 1H), 7.54-7.58 (m, 2H), 7.73-7.76 (m, 1H), 8.70 (s, 1H).

As the paragraph descriping shows that 59434-19-4 is playing an increasingly important role.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; WO2011/130661; (2011); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem