Heterocyclic Building Block-benzofuran

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: To a stirred solution of phthalaldehydic acid 2 (3 mmol) and furan 3 (2.7 mmol;3.3 mmol for 4ab) in acetic acid (8 mL for 4aa, ab?ad; 13 mL for 4ba, ea, fa;20 mL for 4ca, da; 25 mL for 4ga) at room temperature CuBr2 (1.35 mmol;0.27 mmol for 4ea; 0.54 mmol for 4ab) was added. The resulting reactionmixture was stirred for 24 h (18 h for 4aa; 48 h for 4fa) and after reactioncompletion (TLC) was poured into water (150 mL), neutralized with NaHCO3and extracted using DCM (3 40 mL). The combined organic extracts weredried over anhydrous Na2SO4, and the solvent was removed under vacuum.The residue was purified by flash chromatography over silica gel using DCM/petroleum ether (1:1.5, v/v then 2:1, v/v (1:3, v/v for 4ad; 1:6, v/v for 4ac) aseluent and recrystallized from DCM/petroleum ether to afford 3-(fur-2-yl)-3Hisobenzofuran-1-ones 4aa?ad.

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

Reference£º
Article; Shcherbinin, Vitaly A.; Shpuntov, Pavel M.; Konshin, Valery V.; Butin, Alexander V.; Tetrahedron Letters; vol. 57; 13; (2016); p. 1473 – 1475;,
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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

3. Synthesis of benzofuran-5-sulfonyl chloride. 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 0C 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 0C. 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, IH), 8.00 (d, IH), 7.84 (s, IH), 7.44 (d, IH), 6.97 (s, IH). LC/MS (ES) m/z 286 [M+BnH-l]+., 23145-07-5

As the paragraph descriping shows that 23145-07-5 is playing an increasingly important role.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; SCHUMACHER, Richard, A.; TEHIM, Ashok; XIE, Wenge; WO2010/24980; (2010); A1;,
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Benzofuran | C8H6O – PubChem

23145-07-5, 5-Bromobenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(i)3-Hydroxy-4,6-dichloro-1,3-dihydro-3-(benzofuran-5-yl)indole-2-one2.25 g of magnesium for a Grignard reaction in 15 ml of anhydrous THF are placed in a round-bottomed flask equipped with a mechanical stirrer, and under a stream of nitrogen.A mixture of 13.6 g of 5-bromobenzofuran in 35 ml of anhydrous THF is then added.The mixture is stirred for one hour, followed by addition of a solution of 5 g of 4,6-dichloro-1H-indole-2,3-dione in 50 ml of anhydrous THF.The mixture is stirred at room temperature for 4 hours 30 minutes.Water is added and the resulting mixture is extracted with ethyl acetate.The organic phase is separated out, dried over Na2SO4, filtered and evaporated under vacuum.The residue is taken up in ethyl acetate and washed with 1N sodium hydroxide solution.The organic phase is dried over Na2SO4, filtered and evaporated under vacuum.The solid is taken up in ethyl ether and filtered off. 4.2 g of expected product are obtained., 23145-07-5

23145-07-5 5-Bromobenzofuran 90015, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; SANOFI; US2011/312972; (2011); 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.1914-60-9,2,3-Dihydrobenzofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To a mixture of 7 (1 eq) and 1,1?-carbodiimidazole (1.2 eq) in anhydrous THF was stirred for 1h then substituted aniline (0.9 eq) was added at room temperature. After stirring for 14 h, solvent was evaporated then the mixture acidified with 6N HCl to pH 2. The mixture was extracted with EtOAc (3 ¡Á 20 mL). The combined extracts were dried over anhydrous Na2SO4and the solvent was evaporated. After evaporation, the residue was purified by column chromatography (EtOAc/hexane = 1:3 – 1:50).

1914-60-9, 1914-60-9 2,3-Dihydrobenzofuran-2-carboxylic acid 2776555, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Article; Choi, Minho; Jo, Hyeju; Park, Hyun-Jung; Sateesh Kumar, Arepalli; Lee, Joonkwang; Yun, Jieun; Kim, Youngsoo; Han, Sang-Bae; Jung, Jae-Kyung; Cho, Jungsook; Lee, Kiho; Kwak, Jae-Hwan; Lee, Heesoon; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2545 – 2549;,
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Benzofuran | C8H6O – PubChem

496-41-3,496-41-3, Benzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: At 0C, to a solution of 1.0 mmol of benzofuran-2-carboxylic acid in anhydrous THF(20mL),0.135g(1.0mmol) of HOBt and 1.0 mmol of (2S,3R)- 2-Amino-3-hydroxy-N-octylbutanamide, (2S,3R)-2-Amino-3-hydroxy-N- dodecylbutanamide, (2 S,3 R)-2-Amino-3 -hydroxy-N-tetradecylbutanamide, or (2S,3R)-2-Amino-3-hydroxy-N-octadecylbutanamide were added. After 5 min, 0.220g (1.1 mmol) of EDC-HCl was added, and the pH of the solution was adjusted to 8-9 with 4-methylmorpholine. The mixture was stirred at 0 C for 2 h and at room temperature overnight. On evaporation the residue was dissolved in 80 mL of ethyl acetate. The solution was washed successively with saturated sodium bicarbonate, 5% potassium bisulfate, and saturated sodium chloride, and the organic phase was separated and dried over anhydrous magnesium sulfate for 2 h. After filtration and evaporation under reduced pressure crude product was obtained and recrystallized using ethyl acetate to obtain compounds NZJUlh, NZJU2h, NZJU3h, and NZJU4h. N-((2S,3R)-3-hydroxy- 1-oxo- l-(octylamino)butan-2-yl)-benzofuran- 2-carboxamide (NZJUlh) was obtained in a yield of 0.248 g (66.3%) as colorless powder. XH NMR (300 MHz, CDC13) delta 7.70 (d, J= 6.9 Hz, 1H), 7.66 (d, J= 7.8 Hz, 1H), 7.53 (d, J= 8.3 Hz, 1H), 7.48 (s, 1H), 7.46 – 7.37 (m, 1H), 7.33 – 7.27 (m, 1H), 6.96 (s, 1H), 4.61 – 4.42 (m, 2H), 3.36 – 3.12 (m, 2H), 1.57 – 1.41 (m, 2H), 1.37 – 1.06 (m, 13H), 0.83 (t, J= 6.7 Hz, 3H); 13C NMR (75 MHz, CDC13) delta 170.3, 159.8, 155.0, 147.9, 127.3, 123.8, 122.7, 112.0, 11 1.2, 66.8, 57.2, 39.7, 31.8, 29.4, 29.2, 26.9, 22.6, 18.2, 14.1; ESI/MS (m/e) 409.15 [M+Cl]”; Anal. Calcd. For C21H30 2O4: C, 67.35; H, 8.07; N, 7.48%. Found: C, 67.37; H, 8.13; N, 7.39%. N-((2S,3R)-3-hydroxy- 1-oxo- 1 -(dodecylamino)butan-2-yl)- benzofuran- 2-carboxamide (NZJU2h) was obtained in a yield of 0.276 g (64.2%) as colorless powder. XH NMR (300 MHz, CDC13) delta 7.76 – 7.61 (m, 2H), 7.53 (d, J= 8.3 Hz, 1H), 7.48 (s, 1H), 7.47 – 7.38 (m, 1H), 7.31 (d, J = 7.2 Hz, 1H), 6.95 (s, 1H), 4.64 – 4.41 (m, 2H), 3.39 – 3.09 (m, 2H), 1.59 – 1.41 (m, 2H), 1.39 – 1.02 (m, 21H), 0.87 (t, J= 6.6 Hz, 3H); 13C NMR (75 MHz, CDC13) 5 170.6, 159.8, 155.0, 147.8, 127.4, 123.9, 122.7, 112.1, 111.3, 66.6, 56.8, 39.7, 31.9, 29.6, 29.6, 29.5, 29.4, 29.3, 26.9, 22.7,18.2, 14.1; ESI/MS (m/e) 431.10 [M+H]+; Anal. Calcd. For C25H38N2O4: C, 69.74; H, 8.90; N, 6.51%. Found: C, 69.78; H, 8.76; N, 6.44%. N-((2S,3R)-3-hydroxy- 1-oxo- 1 -(tetradecylamino)butan-2-yl)- benzofuran- 2-carboxamide (NZJU3h) was obtained in a yield of 0.323 g (70.5%) as colorless powder. XH NMR (300 MHz, CDC13) delta 7.74 – 7.60 (m, 2H), 7.54 (d, J= 8.3 Hz, 1H), 7.50 (s, 1H), 7.44 (t, J= 7.6 Hz, 1H), 7.31 (t, J = 7.5 Hz, 1H), 6.85 (s, 1H), 4.61 – 4.44 (m, 2H), 3.37 – 3.09 (m, 2H), 1.58 – I.40 (m, 2H), 1.41 – 1.01 (m, 25H), 0.88 (t, J= 6.5 Hz, 3H); 13C NMR (75 MHz, CDC13) 5 170.5, 159.7, 155.0, 147.8, 127.3, 123.8, 122.7, 112.1, 111.2, 66.6, 56.9, 39.7, 31.9, 29.7, 29.5, 29.4, 29.3, 26.9, 22.7, 18.2, 14.1; ESI/MS (m/e) 459.15 [M+H]+; Anal. Calcd. For C27H42N2O4: C, 70.71; H, 9.23; N, 6.11%. Found: C, 70.59; H, 9.29; N, 6.18%. N-((2S,3R)-3-hydroxy- 1-oxo- 1 -(octadecylamino)butan-2-yl)- benzofuran- 2-carboxamide (NZJU4h) was obtained in a yield of 0.362 g (70.4%) as colorless powder. XH NMR (300 MHz, CDC13) delta 7.71 – 7.62 (m, 2H), 7.54 (d, J= 8.3 Hz, 1H), 7.50 (s, 1H), 7.48 – 7.40 (m, 1H), 7.30 (t, J= 7.2 Hz, 1H), 6.87 (s, 1H), 4.59 – 4.44 (m, 2H), 3.35 – 3.15 (m, 2H), 1.57 – 1.43 (m, 2H), 1.36 – 1.11 (m, 33H), 0.88 (t, J= 6.6 Hz, 3H); 13C NMR (75 MHz, CDCI3) delta 170.4, 159.7, 155.0, 147.8, 127.3, 123.8, 122.7, 112.0, 111.2, 66.6, 56.9, 39.7, 31.9, 29.7, 29.6, 29.5, 29.4, 29.3, 26.9, 22.7, 18.2, 14.1; ESI/MS (m/e) 515.25 [M+H]+; Anal. Calcd. For C31H50N2O4: C, 72.33; H, 9.79; N, 5.44%. Found: C, 72.31; H, 9.81; N, 5.43%.

The synthetic route of 496-41-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ZHEJIANG UNIVERSITY; GEORGIA REGENTS RESEARCH INSTITUTE, INC.; LIU, Feiyan; LIU, Kebin; HUANG, Zhizhen; WU, Ping; WO2014/66613; (2014); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

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

Example-2: preparation of ethyl-5-amino-l-benzofuran-2-carboxylate To a solution of ethyl-5-nitro- 1 -benzofuran-2-carboxylate (100g) in Ethyl acetate (800ml) was added 10% palladium on carbon (4.0g). The reaction mixture was stirred under an atmosphere of hydrogen at 33-38C with 4-5kg/cm2 hydrogen pressure for 4-6 hrs. After completion of the reaction, reaction mixture was filtered through hyflo, washed with ethyl acetate. The filtrate was concentrated in vacuo to give ethyl-5-amino-l-benzofuran-2- carboxylate yield: 100%

69604-00-8 Ethyl 5-nitrobenzofuran-2-carboxylate 1382954, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; ALEMBIC PHARMACEUTICALS LIMITED; JAYARAMAN, Venkat Raman; RATHOD, Dhiraj; VOHRA, Irfan; BHUJADE, Vinayak; MODI, Viral; GANDHI, Ojas; BUDH, Mayur; WO2013/153492; (2013); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

1914-60-9, 2,3-Dihydrobenzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 3a (0.30 g, 2.00 mmol) in THF and sat. aq NaHCO3 (1:1,12 mL) was stirred at r.t. and then TEMPO (59.1 mg, 0.38 mmol) and KBr (60.7 mg, 0.51 mmol) were added. A solution of aq NaOCl (2.5% w/v, 2 mL) was introduced in the reaction mixture. The mixture was stirred at r.t. for 3 h and then transferred to a separating funnel and treated with aq 1 N NaOH (25 mL). The aqueous layer was acidified with HCl (37% w/w) to pH 1 and extracted with CH2Cl2 (3 ¡Á 20 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude acid was used in the next step. The crude acid was added to SOCl2 (2.90 mL, 40.00 mmol) at 60 C and kept for 6 h. The reaction mixture was then concentrated in vacuo. The mixture was diluted with Et2O (2 ¡Á 5 mL) and concentrated in vacuo again. The crude acid chloride was used in the next step. To a solution of the crude acid chloride in anhyd CH2Cl2 (5 mL) was added a solution of p-nitroaniline (1.10 g, 8.00 mmol) in anhyd CH2Cl2(10 mL) and the mixture was stirred at 50 C for 72 h. The crude mixture was concentrated in vacuo and purified by flash column chromatography (20% EtOAc in PE) to afford the desired product 1d; white solid; yield: 312.3 mg (55%); mp 109-112 C., 1914-60-9

1914-60-9 2,3-Dihydrobenzofuran-2-carboxylic acid 2776555, abenzofuran compound, is more and more widely used in various.

Reference£º
Article; Triandafillidi, Ierasia; Sideri, Ioanna K.; Tzaras, Dimitrios Ioannis; Spiliopoulou, Nikoleta; Kokotos, Christoforos G.; Synthesis; vol. 49; 18; (2017); p. 4254 – 4260;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

6296-53-3, N-(1,3-Dioxo-1,3-dihydroisobenzofuran-4-yl)acetamide is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6296-53-3, [0110j A stirred solution of 1 -(3 -ethoxy-4-methoxyphenyl)-methylsulfonylethylamine (1.0 g, 3.7 mmol) and 3-acetamidophthalic anhydride (751 mg, 3.66 mmol) in acetic acid (20 mL) was heated at reflux for 15 h. The solvent was removed in vacuo to yield an oil. Chromatography of the resulting oil yielded the product as a yellow solid (1.0 g, 59% yield): mp, 144C.; ?H NMR (CDC13) oel.47 (t, J=7.0 Hz, 3H, CH3), 2.26 (s, 3H, CH3), 2.88 (s,3H, CH3),3.75 (dd, J4.4, 14.3 Hz, 1H, CHH), 3.85 (s, 3H, CH3), 4.11 (q, J 7Hz, 2H, CH2), 5.87 (dd, J4.3, 10.5 Hz, 1H, NCH), 6.82-6.86 (m, 1H, Ar), 7.09-7.11 (m, 2H, Ar), 7.47 (d, J= 7 Hz, 1H., Ar), 7.64 (t, J= 8 Hz, 1H, Ar), 8.74 (d, J= 8 Hz, 1H, Ar), 9.49 (br s, 1H, NH); ?3C NMR (CDC13) oe14.61, 24.85, 41.54, 48.44, 54.34, 55.85, 64.43, 111.37, 112.34, 115.04, 118.11, 120.21, 124.85, 129.17, 130.96, 136.01, 137.52, 148.54, 149.65, 167.38, 169.09, 169.40; Anal Calc?d. for C22H24N075: C, 57.38; H, 5.25; N, 6.08. Found: C, 57.31; H, 5.34; N, 5.83.

6296-53-3 N-(1,3-Dioxo-1,3-dihydroisobenzofuran-4-yl)acetamide 226121, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; CELGENE CORPORATION; SCHAFER, Peter; KORISH, Shimon; (45 pag.)WO2015/175773; (2015); 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.4265-16-1,Benzo[b]furan-2-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: An aldehyde (3.24 mmol) was dissolved in EtOH (12 mL), then a solution of NH2OH*HCl (360 mg, 5.18 mmol) and Na2CO3 (247 mg,2.33 mmol) in water (3 mL) was added, and the mixture was boiled at reflux temp for 20 min. Saturated aqueous NaCl solution (30 mL)was added, and the mixture was extracted by EtOAc (2 20 mL).The combined organic layers were dried (MgSO4) and evaporated to give the expected aldoxime which was used without further purification.

4265-16-1, 4265-16-1 Benzo[b]furan-2-carboxaldehyde 61341, abenzofuran compound, is more and more widely used in various.

Reference£º
Article; Goyard, David; Konya, Balint; Chajistamatiou, Aikaterini S.; Chrysina, Evangelia D.; Leroy, Jeremy; Balzarin, Sophie; Tournier, Michel; Tousch, Didier; Petit, Pierre; Duret, Cedric; Maurel, Patrick; Somsak, Laszlo; Docsa, Tibor; Gergely, Pal; Praly, Jean-Pierre; Azay-Milhau, Jacqueline; Vidal, Sebastien; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 444 – 454;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.127264-14-6,5-(2-Bromoethyl)-2,3-dihydrobenzofuran,as a common compound, the synthetic route is as follows.

5-(2-Bromoethyl)benzo[2,3-b]furan (17.2 g) was added to the mixture of 3-(S)- (+)-( 1 -carbamoyl- 1 , 1 -diphenylmethyl)pyrrolidine.L-(+)-tartrate (25 g), potassium hydroxide (11.4 g) in acetonitrile solvent at 25-35¡ã C. Reaction mass was heated to 40- 45¡ã C and maintained up to completion of the reaction . The reaction mass was then cooled to R.T and extracted with dichloromethane, the solvent distilled off under vacuum to give residue. Acetone was added to the residue and cooled to 10-15¡ã C. Hydrobromic acid was added to the above solution and heated to 20-25¡ã C and maintained for 10-12 hours. The reaction mass is filtered to give darifenacin hydrobromide., 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; MATRIX LABORATOIRES LIMITED; WO2009/125430; (2009); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem