Heterocyclic Building Block-benzofuran

123654-26-2, 4-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 4-amino-5-chloro-2,3-dihydro benzofuran-7-carboxylic acid (Chem. Pharm. Bull. 1998, 46{), 42-52; 3.93 g, 18.4 mmol) in methanol (36.8 mL), cooled at 0 C, thionyl chloride (6.0 mL) was added. The reaction mixture was gradually warmed to room temperature and was heated to reflux for 2 hours. The volatiles were removed under reduced pressure; the crude mass was diluted with aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and the solvent was removed under vacuum to obtain methyl 4-amino-5-chloro-2,3-dihydro benzofuran-7-carboxylate (3.89 grams). Yield: 92.9 % ? – NMR (DMSO-de): delta 7.43 (s, 1H), 6.06 (bs, 2H), 4.60 (t, J = 8.8 Hz, 2H), 3.68 (s, 3H), 2.97 (t, J = 8.8 Hz, 2H); Mass (m/z): 228.0, 230.1 (M+H)+.

123654-26-2, The synthetic route of 123654-26-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; MOHAMMED, Abdul Rasheed; YARLGADDA, Suresh; RAVELLA, Srinivasa Rao; SHINDE, Anil Karbhari; KAMBHAMPATI, Ramasastri; ROAYALLEY, Praveen Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; PATNALA, Sriramachandra Murthy; RAVULA, Jyothsna; JASTI, Venkateswarlu; WO2013/42135; (2013); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

66158-96-1, (2,3-Dihydrobenzofuran-2-yl)methanol is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

66158-96-1, 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.

The synthetic route of 66158-96-1 has been constantly updated, and we look forward to future research findings.

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

28418-88-4, 4-Iodoisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1; Preparation of 3-iodo-N,N-diethylphthalamidic acid . To 15 ml of an acetonitrile solution containing 2.0 g of 3-iodophthalic anhydride was added dropwise 0.7 g of diethylamine under ice-cooling and stirring, and after completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the precipitated solid were collected by filtration, washed with a small amount of acetonitrile to obtain 1.5 g of the objective material as pale yellowish crystals. Melting point 120.0 to 122.0C1H NMR (CDCl3, Me4Si, 300MHz) delta 8.28 (bs, 1 H), 8.05 (d, J=8.5Hz, 1 H), 7.98 (d, J=8.5Hz, 1 H), 7.0-7.2 (m, 1 H), 3.67 (q, J=7.2Hz, 2H), 3.49 (q, J=7.2Hz, 2H), 1.12 (t, J=7.2Hz, 3H), 1.10 (t, J=7.2Hz, 3H).

28418-88-4, 28418-88-4 4-Iodoisobenzofuran-1,3-dione 282071, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; NISSAN CHEMICAL INDUSTRIES, LIMITED; EP1538138; (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.652-39-1,4-Fluoroisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

652-39-1, 3-Fluorophthalic anhydride (377 mg, 2.27 mmol) was dissolved in MeOH (6 ml_) and heated to reflux for 15 h. The mixture was concentrated in vacuo and the two products (400 mg, 89percent), 2-fluoro-6-(methoxycarbonyl)benzoic acid and 3-fluoro-2- (methoxycarbonyl)benzoic acid, were taken on to the next step without purification.; Step B: (Z)-Methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-3- fluorobenzoate. To a heterogeneous mixture of the two acids from step A (400 mg, 2 mmol) at 0 ¡ãC in DCM (5 ml_) was added oxalyl chloride (0.244 ml_, 2.32 mmol) followed by DMF (0.05 ml_). Gas evolution commenced immediately and after 5 min the ice bath was removed. When gas evolution had ceased and the mixture was homogeneous an aliquot was removed and quenched with MeOH. Formation of the methyl ester was confirmed by HPLC and the mixture was concentrated in vacuo. The viscous liquid was dissolved in fresh DCM (5 ml_) and treated with solid N-hydroxyacetamidine (165 mg, 2.22 mmol) in several portions followed by TEA (0.351 ml_, 2.52 mmol). After stirring for 14 h at ambient temperature the mixture was concentrated in vacuo.Chromatography (Hex to 100percent EtOAc/Hex) afforded two products (477 mg, 94percent), (Z)-methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-3- fluorobenzoate and (Z)-methyl 2-((((1 -aminoethylidene)amino)oxy)carbonyl)-6- fluorobenzoate, which were taken on to the next step as a mixture. MS (ESI) mass calculated for Cn H FN2O4, 254.07; m/z found, 255.0.; Step C: 3-Fluoro-2-(3-methyl-1 ,2,4-oxadiazol-5-yl)benzoic acid. To the mixture of products from Step B (477 mg, 1 .88 mmol) in t-BuOH (9 ml_) was added NaOAc (156 mg, 1 .88 mmol). The mixture was heated at 90 ¡ãC for 50 h and then concentrated in vacuo. This resulted in four products. The residue was dissolved in 1 M aq. K2CO3 and extracted with DCM to isolate methyl 2- fluoro-6-(3-methyl-1 ,2,4-oxadiazol-5-yl)benzoate and methyl 3-fluoro-2-(3- methyl-1 ,2,4-oxadiazol-5-yl)benzoate along with unreacted (Z)-methyl 2-((((1 – aminoethylidene)amino)oxy)carbonyl)-3-fluorobenzoate. The aqueous layer was then acidified with concentrated HCI and extracted with DCM. The combined organic layers from this extraction were dried over Na2SO4, filtered and concentrated in vacuo. The acid isomers were purified on a Prep Agilent system with a XBridge Ci8 OBD 50×100 mm column eluting with 5 to 99percent 0.05percent NH4OH in H2O/ACN over 17 min to afford the desired product (63 mg, 15percent) as a white solid after acidification with 1 M aq. HCI in Et2O. MS (ESI) mass calculated for C10H7FN2O3, 222.04; m/z found, 223.0.; Intermediate 69: 2-Fluoro-6-(3-methyl-1 ,2,4-oxadiazol-5-yl)benzoic acid.The title compound was isolated from the synthesis of Intermediate 68, Method A. MS (ESI) mass calculated for Ci0H7FN2O3, 222.04; m/z found, 223.0. 1H NMR (500 MHz, CDCI3): 7.89 (d, J = 7.7, 1 H), 7.65 – 7.59 (m, 1 H), 7.44 – 7.38 (m, 1 H), 2.50 (s, 3H).

The synthetic route of 652-39-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
Benzofuran – Wikipedia
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

To toluene 3.0mL suspension of tert-butyl 2-amino-4-phenylbenzoate 0.10g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9mg, tris(dibenzylideneacetone)dipalladium(0) 3mg and cesium carbonate 0.24g was added 5-bromobenzofuran 0.18g, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9mg and tris(dibenzylideneacetone)dipalladium(0) 3mg were added to it, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9mg and tris(dibenzylideneacetone)dipalladium(0) 3mg were added to it, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10percent citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=30:1] to give tert-butyl 2-((benzofuran-5-yl)amino)-4-phenylbenzoate. Trifluoroacetic acid 3.0mL solution of the obtained tert-butyl 2-((benzofuran-5-yl)amino)-4-phenylbenzoate was stirred at room temperature for 3 hours. The solvent of reaction mixture was removed under reduced pressure, and the obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate:acetic acid=30:10:1] to give 2-((benzofuran-5-yl)amino)-4-phenylbenzoic acid 42mg. 1H-NMR(DMSO-d6) delta value: 6.95(1H,dd,J=2.2,0.7Hz),7.01(1H,dd,J=8.3,1.7Hz),7.23(1H ,d,J=1.4Hz),7.28(1H,dd,J=8.8,2.2Hz),7.34-7.46(3H,m),7.52-7.54(2H,m),7.61-7.64(2H,m),7.98(1H,d,J=8.3Hz),8.01(1H,d,J=2.2Hz),9.64-9.76(1H,broad),12.88-13.20(1H,broad).

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; TOYAMA CHEMICAL CO., LTD.; EP1860098; (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.23681-89-2,2,3-Dihydrobenzofuran-6-ol,as a common compound, the synthetic route is as follows.

General procedure: NaH (12.0mmol) was added to a solution of 1 or 722 (1.88g, 10.0mmol) and substituted phenol (12.0mmol) in DMF (50mL) at room temperature under N2, and the mixture was stirred at 80¡ãC for 10h. Water was added to the cooled mixture, and the mixture was extracted with EtOAc several times. The combined organic layers were washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography to obtain purified compound 2, or crude 2 was used directly for the next reaction without further purification., 23681-89-2

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

Reference£º
Article; Shinozuka, Tsuyoshi; Tsukada, Tomoharu; Fujii, Kunihiko; Tokumaru, Eri; Shimada, Kousei; Onishi, Yoshiyuki; Matsui, Yumi; Wakimoto, Satoko; Kuroha, Masanori; Ogata, Tsuneaki; Araki, Kazushi; Ohsumi, Jun; Sawamura, Ryoko; Watanabe, Nobuaki; Yamamoto, Hideki; Fujimoto, Kazunori; Tani, Yoshiro; Mori, Makoto; Tanaka, Jun; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 5099 – 5117;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1207453-90-4,6-Fluoro-4-nitroisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of 6-fluoro-4-nitroisobenzofuran-1(3H)-one (1) (10 g, 50.8 mmol), 2-methyl-2H-1,2,4-triazole-3-carbaldehyde (2) (11 g, 101.5 mmol) and Et3N (20 mL, 152.4 mmol) in anhydrous THF (150 mL) was added acetic anhydride (35 mL) drop-wise with stirring at room temperature in 3 minutes. The mixture was then stirred at reflux for 45 minutes when a green solid was precipitated from solvent. The solvent was concentrated to 15 mL and the resulting mixture was cooled to 0 C. and filtered, washed with 15 mL of ethyl acetate to obtain (Z)-6-fluoro-3((1-methyl-1H-1,2,4-triazol-5-yl)methylene)-4-nitroisobenzofuran-1(3H)-one (3) as a green solid (11.5 g, yield: 78%). LC-MS (ESI) m/z: 291 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) delta (ppm): 3.94 (s, 3H), 7.15 (s, 1H), 8.10 (s, 1H), 8.40-8.42 (dd, J1=6.4 Hz, J2=2.4 Hz, 1H), 8.58-8.61 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H).

1207453-90-4, The synthetic route of 1207453-90-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BioMarin Pharmaceutical, Inc.; Wang, Bing; Chu, Daniel; US2013/53365; (2013); 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.58546-89-7,Benzofuran-5-amine,as a common compound, the synthetic route is as follows.

Example 58 (2521) 3-(Benzofuran-5-ylamino)-7-chloro-5-hydroxy-2H-benzoreiri ,2,41thiadiazine 1 ,1 – dioxide (2522) To a suspension of of 3-bromo-7-chloro-5-hydroxy-4H-benzo[e][1 ,2,4]thiadiazine 1 ,1 – dioxide (lnt-3, 200 mg) and benzofuran-5-amine (103 mg) in t-BuOH (10 mL) stirred under nitrogen was added KH2P04 (105 mg) in one portion. The reaction mixture was stirred at 80 C for 24 hr. The reaction mixture was allowed to cool to RT, then was concentrated under reduced pressure, diluted with deionized water (15 mL) and allowed to stir for 15 min. The resulting precipitate was collected by filtration and washed with water (2 x 5 mL) and diethyl ether (3 x 5 mL), and dried to afford the titled compound (160 mg). LCMS m/z 364.00 (M+H). 1H NMR after D20 exchange(400 MHz, DMSO-c/6) delta ppm 7.02 (d, J=1 .53 Hz, 1 H) 7.10 (d, J=2.19 Hz, 1 H) 7.19 (d, J=1 .97 Hz, 1 H) 7.33 (dd, J=8.77, 2.19 Hz, 1 H) 7.63 (d, J=8.77 Hz, 1 H) 7.87 (d, J=2.19 Hz, 1 H) 8.00 (d, J=2.19 Hz, 1 H)., 58546-89-7

58546-89-7 Benzofuran-5-amine 1477152, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

209256-42-8, 2,3-Dihydrobenzofuran-4-carbaldehyde is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirring solution of the aldehyde from step A Example 33 (400 mg, 2.7 mmol) in dichloromethane (40 mL) was added carbethoxymethylene-triphenylphosphorane (1.41 g, 4.05 mmol). The reaction was refluxed for 16 hrs. and the solvent was removed in vacuo. The title compound (white solid, 533 mg, 91% yield) was isolated from a silica gel column using 20% ethyl acetate in hexanes as the eluent., 209256-42-8

209256-42-8 2,3-Dihydrobenzofuran-4-carbaldehyde 18787449, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; US6887870; (2005); B1;,
Benzofuran – Wikipedia
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.,569-31-3

Example V — SYNTHESIS OF 3-[N(BENZODIOXAN-1,4 YL-6) AMINO] 6,7-DIMETHOXY 3H-ISOBENZOFURANONE A mixture of 30 g of 6,7-dimethoxy 3H-isobenzofuranone, prepared according to the method described in Example IV, 1 liter of ethanol and 300-400 cm3 of dimethylamine was agitated for several hours and then evaporated under vacuum at 30 – 35 C. The crystallized product was washed with heptane. The 2,3-dimethoxy N,N-dimethyl 6-hydroxymethyl benzamide was obtained in a yield of 100%. F = 90 C.

The synthetic route of 569-31-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Societe Cortial; US4122202; (1978); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem