23681-89-2 | Heterocyclic Building Block-benzofuran

Awesome Chemistry Experiments For 2,3-Dihydrobenzofuran-6-ol

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Indazoles represent a privileged scaffold in medicinal chemistry. In the presence of strong base, however, N-protected indazoles are prone to an undesirable ring-opening reaction to liberate o-aminobenzonitriles. By employing unprotected indazoles with a free N-H bond, isomerization is averted because the heterocycle is deprotonated in situ. We herein report functional group-tolerant and robust C-S couplings of bromoindazoles with thiols of varying electronic nature in the presence of lithium bis(trimethylsilyl)amide at elevated temperatures.

Reference：
Benzofuran – Wikipedia,
Benzofuran | C8H581O – PubChem

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Reference of 23681-89-2, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 23681-89-2, molcular formula is C8H8O2, introducing its new discovery.

Methionine aminopeptidase 2 (MetAP2) is an enzyme that cleaves an N-terminal methionine residue from a number of newly synthesized proteins. Pre-clinical and clinical studies suggest that MetAP2 inhibitors could be used as a novel treatment for obesity. Herein we describe our use of fragment screening methods and structural biology to quickly identify and elaborate an indazole fragment into a series of reversible MetAP2 inhibitors with <10 nM potency, excellent selectivity, and favorable in vitro safety profiles. The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 23681-89-2 is helpful to your research. Reference of 23681-89-2

Reference：
Benzofuran – Wikipedia,
Benzofuran | C8H580O – PubChem

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The present invention relates to novel indazole derivatives (I) having pharmacological activity, processes for their preparation, compositions containing them and uses of these compounds in the treatment of estrogen receptor beta mediated diseases.

Reference：
Benzofuran – Wikipedia,
Benzofuran | C8H579O – PubChem

Downstream synthetic route of 23681-89-2

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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

To a cooled (0 ¡ãC) solution of 2,3-dihydrobenzofuran-6-ol (0.52 g, 3.8 mmol) in anhydrous tetrahydrofuran (25 ml.) was added isopropylmagnesium chloride (2.1 ml_, 2 M solution in tetrahydrofuran, 4.2 mmol). The resultant suspension was stirred at 0 ¡ãC for 0.5 h and followed by the addition of 7-chloro-1-(diphenylmethyl)-1H-indole-2,3- dione (2.11 g, 15.5 mmol) in one portion. The reaction mixture was stirred at ambient temperature for 3 h and concentrated in vacuo. The crude product was purified by column chromatography with ethyl acetate in hexanes (0percent to 50percent gradient) to afford 7-chloro-1-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)- 1 ,3-dihydro-2H-indol-2-one (7.12 g, 95percent) as a colorless solid: 1H NMR (300 MHz, DMSO-CZ6) .pound.9.43 (s, 1 H), 7.56-7.18 (m, 13H), 6.99-6.86 (m, 2H), 6.60 (s, 1 H), 6.08 (s, 1H), 4.56 (t, J = 8.6 Hz, 2H), 3.10 (t, J = 8.6 Hz, 2H). C. Synthesis of 7-chloro-1 -(diphenylmethyl)-3-(6-hvdroxy-2,3-dihydro-1 – benzofuran-5-yl)-1,3-dihydro-2/-/-indol-2-one, 23681-89-2

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Reference£º
Patent; XENON PHARMACEUTICALS, INC.; CHAFEEV, Mikhail; CHOWDHURY, Sultan; FRASER, Lauren; FU, Jianmin; LANGILLE, Jonathan; LIU, Shifeng; SUN, Jianyu; SUN, Shaoyi; SVIRIDOV, Serguei; WOOD, Mark; ZENOVA, Alla; JIA, Qi; CADIEUX, Jean-Jacques; GAUTHIER, Simon, J.; DOUGLAS, Amy Frances; HSIEH, Tom; CHAKKA, Nagasree; CIKOJEVIC, Zoran; WO2010/45251; (2010); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Downstream synthetic route of 23681-89-2

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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

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

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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 15 10.9 g. of 6-hydroxy-2,3-dihydrobenzofuran are dissolved in 80 ml. of anhydrous dimethylformamide and treated, while stirring and with ice cooling at 0¡ã C. with 5.3 g. of freshly powdered potassium hydroxide. The mixture is stirred for 1 hour at 0¡ã C. under a nitrogen atmosphere and then added dropwise within 1 hour to a solution of 19.6 g. of 1-bromo-7-ethyl-3-methyl-2,6-nonadiene in 10 ml. of absolute tetrahydrofuran. The mixture is allowed to stir for 2 hours at 0¡ã C. and for 2 hours at room temperature and then poured onto a mixture of 100 ml. of 10percent by weight aqueous sodium hydroxide and 100 ml. of ice-water. The mixture is extracted three times with pentane, the extracts are washed successively with 10percent by weight aqueous sodium hydroxide, water and saturated 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-ethyl-3-methyl-2,6-nonadienyl)-oxy]-2,3-dihydrobenzofuran which is distilled in a bulb-tube at 132¡ã C./0.02 mmHg; nD20 = 1.5350., 23681-89-2

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

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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

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

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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

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EXAMPLE 7 275 mg. of a 55percent sodium hydride dispersion in oil are washed under nitrogen three times with absolute tetrahydrofuran and then covered with 5 ml. of absolute tetrahydrofuran. Thereafter, the mixture is cooled to 0¡ã C. and treated dropwise while stirring with a solution of 0.85 g. of 6-hydroxy-2,3-dihydrobenzofuran in 10 ml. of absolute tetrahydrofuran. The mixture is stirred for one hour at room temperature, again cooled to 0¡ã C. and 1.22 g. of 1-bromo-3,7,7-trimethyl-2,4-octadiene dissolved in 10 ml. of absolute tetrahydrofuran are added. Subsequently, the mixture is diluted with 10 ml. of absolute hexamethylphosphoric acid triamide, the ice bath removed and the mixture stirred for 2 hours. Thereafter, 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-[(3,7,7-trimethyl-2,4 -octadienyl)-oxy]-2,3-dihydrobenzofuran which is distilled in a bulb-tube at 130¡ã C./0.02 mmHg; nD20 = 1.5438.

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

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Preparation 1 benzaldehyde (221 mg, 1.25 mmol), Preparation 12 phenol (170 mg, 1.25 mmol), K2CO3 (518 mg, 3.75 mmol), and DMF (5 mL) were combined and heated at 100¡ã C. for 24 h. The mixture was cooled to rt, poured into H2O and extracted with EtOAc (2.x.). The combined extracts were washed with 1M NaOH and brine, dried (MgSO4), filtered, concentrated, and chromatographed (loaded with CH2Cl2; eluted with 10percent EtOAc in hexanes). The isolated solid (140 mg) was dissolved in acetonitrile (10 mL) at rt. To the solution was added acetic acid (0.082 mL, 1.44 mmol) and methylamine (0.479 mL of a 2M solution in THF, 0.957 mmol). After 1 h NaBH(OAc)3 (152 mg, 0.718 mmol) was added. The mixture was stirred at rt for 3 d, poured into sat. NaHCO3 (50 mL) and 1 M NaOH (5 mL) and extracted with EtOAc (2.x.50 mL). The combined extracts were dried (MgSO4), filtered, concentrated, and chromatographed (loaded with CH2Cl2; eluted with 10percent MeOH in CH2Cl2). The resulting yellow gum was dissolved in EtOAc (3 mL) at rt and p-toluenesulfonic acid hydrate (70 mg) was added. After 14 h the mixture was filtered and the resulting solid dried under high vacuum to provide 100 mg of the above named compound as a solid. MS (M+)=308, 310. 1H NMR (400 MHz, CD3OD): delta 7.69 (d, 2, J=9.1), 7.25 (s, 1), 7.22 (d, 2, J=8.1), 6.90 (d, 1, J=6.4), 6.56 (dd, 1, J=7.9, 2.3), 6.52 (d, 1, J=2.1), 4.62 (t, 2, J=8.7), 4.27 (s, 2), 3.21 (t, 2, J=8.7), 2.76 (s, 3), 2.36 (s, 3)., 23681-89-2

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Reference£º
Patent; Pfizer Inc; US2006/58361; (2006); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem