Heterocyclic Building Block-benzofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7169-34-8,Benzofuran-3(2H)-one,as a common compound, the synthetic route is as follows.

General procedure: Coumaranone (1.00mmol) and aldehyde (1.00mmol) were combined in a dry microwave vial. 1ml of the deep eutectic solvent formed from a 1:2M ratio of choline chloride and urea was added. The reaction mixture was heated to 90C in a CEM Discover microwave with stirring for 30min. At this point, the reaction was cooled to room temperature and partitioned between water and methylene chloride. The organic layer was separated and concentrated to dryness in vacuo. Further purification was performed as noted.

7169-34-8 Benzofuran-3(2H)-one 23556, abenzofuran compound, is more and more widely used in various.

Reference£º
Article; Park, Hyo S.; Nelson, David E.; Taylor, Zachary E.; Hayes, James B.; Cunningham, Kirsten D.; Arivett, Brock A.; Ghosh, Rajarshi; Wolf, Larissa C.; Taylor, Kimberley M.; Farone, Mary B.; Handy, Scott T.; Farone, Anthony L; International Immunopharmacology; vol. 43; (2017); p. 116 – 128;,
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27550-59-0, 5-Hydroxyisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6th Stage: 4-[11-(acryloyl-methyl-amino)-undecyloxy]phthalic Acid (AAUPA) (0095) (0096) 4-hydroxyphthalic anhydride (6.70 g; 40.8 mmol), BHT (10 mg) and N-(11-bromoundecyl)-N-methyl acrylamide (13.00 g; 40.8 mmol) were dissolved in N,N-dimethylformamide (100 ml). Potassium carbonate (5.64 g; 40.8 mmol) was added. The yellow suspension was stirred at RT. Water (200 ml) was added to the reaction mixture after 20 d and the whole stirred for 1 h at RT. An oily white solid precipitated from the initially cloudy solution. The solvent was decanted off. The residue was dissolved in dilute aqueous Na2CO3 solution (5%; 100 ml). The milky/cloudy aqueous phase was washed with MtBE (5¡Á100 ml). Diluted hydrochloric acid (2N, 100 ml) was added to the water phase (pH=1) and extraction with MtBE (8¡Á100 ml) took place. The combined extracts were dried over Na2SO4, filtered and concentrated on the rotary evaporator. Chloroform (150 ml) was added to the residue and the whole stirred at RT. After 20 h the suspension was filtered. The filtration residue was washed with chloroform (50 ml) and discarded. The filtrate was concentrated on the rotary evaporator. The residue was dissolved in chloroform (50 ml). Acetonitrile (50 ml) was added. After 72 h storage at -18 C. the solvent was decanted off and the residue dried under a fine vacuum. 3.84 g (9.2 mmol; 22% yield) of a white solid was obtained (melting point: 95 C.), which dissolves very well e.g. in ethanol or acetone. (0097) 1H-NMR (DMSO-d6, 400 MHz): delta (2 isomers)=1.15-1.35 (m, 12H), 1.36-1.50 (m, 4H), 1.68-1.75 (m, 2H), 2.86 (s, 1.7H), 3.00 (s, 1.3H), 3.29-3.36 (m, 2H), 4.04 (t, 2H; J=6.4 Hz), 5.61-5.65 (m, 1H), 6.06-6.13 (m, 1H), 6.72 (dd, 1H; J=10.7 Hz, 16.9 Hz), 7.03-7.08 (m, 2H), 7.73 (d, 1H; J=8.4 Hz), 12.89 (br, 2H). (0098) 13C-NMR (DMSO-d6, 100 MHz): delta=24.3, 24.8, 25.2, 25.5, 27.3, 27.5, 27.6, 27.7, 27.8, 27.9, 32.2, 33.7, 45.8, 47.8, 66.9, 112.3, 114.2, 121.3, 125.6, 127.2, 127.6, 130.1, 136.0, 159.7, 164.0, 166.2, 168.1.

The synthetic route of 27550-59-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ivoclar Vivadent AG; Bock, Thorsten; Fischer, Urs Karl; Lamparth, Iris; Moszner, Norbert; Rheinberger, Volker; (9 pag.)US9393181; (2016); B2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.52010-22-7,4-Chlorophthalide,as a common compound, the synthetic route is as follows.

A 45.85 g sample of an oxidation mixture in acetic acid from the oxidation of 3- and 4-chloroxylene in the presence of a catalyst composition comprising cobalt and manganese was treated with 0.143 g. of oxalic acid dihydrate and brought to reflux for 30 minutes (this process removed about 90% of the cobalt and >50% of the manganese by precipitation as the oxalate salts). The solution was then passed through a glass frit under vacuum. The remainder of the solvent was removed by evaporation (down to 16.2 g.) and distillation (down to 14.0 g. residue). The remaining light yellow solid was combined with 60 ml. of water and 40 ml. of toluene, and mixed. There was some emulsion layer which was treated in a second wash with an additional 15 ml. each of water and toluene. The solvent was removed by evaporation of each fraction to leave 10.6 g. in the water fraction and 2.7 g. in the toluene fraction. The fractions were analyzed by GC. The analytical results are shown in Table 7.

The synthetic route of 52010-22-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; General Electric Company; US6670487; (2003); B1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.37418-88-5,4-Hydroxyisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

A mixture of 3-hydroxyphthalic anhydride (543 mg, 3.31 mmol), 4-methoxybenzylamine (0.43 mL, 3.31 mmol) and acetic acid (3 mL) was heated at 1000C for 4 hours. The mixture was allowed to cool and diluted with water (20 mL). The white solid was collected by filtration, washed well with water and dried to give the title compound (760 mg, 81 percent). 1H NMR (DMSOd6) 11.03 (1H, s), 7.61 (1H, dd), 7.28 (1 H, d), 7.23-7.19 (3H, m), 6.89-6.86 (2H, m), 4.63 (2H, s), 3.71 (3H, s). MS: [M-H+] 282.

As the paragraph descriping shows that 37418-88-5 is playing an increasingly important role.

Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
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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.

A mixture of 44.4 g (0.37 moles) of 2,3-dihydrobenzofuran and 37.8 g (0.37 moles) of acetic anhydride were added with 5.0 g (37 mmoles) of anhydrous zinc chloride. The mixture was heated to 95-105 0C for 10 hrs; after cooling to room temperature the mixture is added with 50 ml of water and 50 ml of dichloromethane. The organic phase was separated and the aqueous phase was extracted twice with dichloromethane (2x 30 ml). The organic phases were collected together, and washed with 50 ml of a saturated aqueous solution of sodium carbonate. The organic phase was separated and evaporated u.v. (20 ¡ãC/21 mbar). The residue was then distilled at 99-100 ¡ãC/0.08 mbar obtaining 14.5 g (0.089 moles) of 5-acetyl-2,3- dihydrobenzofuran. 1H NMR (400 MHz; CDCI3): delta: 2.50 (s, 3H); 3.20 (t, 2H, J = 8.7 Hz); 4.64 (t, 2H, J = 8.7 Hz); 6.76 (d, 1 H, J = 8.4 Hz); 7.76 (m, 1 H); 7.81 (m, 1 H).13C-NMR (CDCI3, 100MHz): delta: 26.22; 28.79; 72.02; 108.72; 125.34; 127.50; 130.17; 130.48; 164.19; 196.41.

As the paragraph descriping shows that 496-16-2 is playing an increasingly important role.

Reference£º
Patent; ENDURA S.P.A.; ROTHAMSTED RESEARCH LTD.; BORZATTA, Valerio; CAPPARELLA, Elisa; MORONI, Leni; MOORES, Graham; PHILIPPOU, Despina; WO2011/20848; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.942-06-3,4,5-Dichlorophthalic Anhydride,as a common compound, the synthetic route is as follows.

To a solution of 5, 6-dichloroisobenzofuran-1, 3-dione (8.8 g, 40.6 mmol) in acetic acid (40 mL), hydrazine (1.886 ml, 48.7 mmol) was added carefully at room temperature. The mixture was stirred at 70 ¡ãC overnight under nitrogen. The reaction mixture was cooled and the solid material was collected to give the title compound, which was used without further purification (8.9 g, 90percent). LCMS (Method B): m/z 231.7 (M+H), retention time: 1.38 minutes. ?H NIVIR (DMSO-d6, 400 IVIHz) oe 11.88 (s, 2H), 8.18 (s, 2H).

942-06-3 4,5-Dichlorophthalic Anhydride 70334, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; DAI, Yujia; MICHAELIDES, Michael; (83 pag.)WO2016/123796; (2016); A1;,
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125-20-2, Thymolphthalein is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

preparation method as follow: thymolphthalein (4.3 g, 10 mmol), TBAHS (3. 4 g, 10 mmol), 2-acetamido-3,4,6 -tri-O-acetyl -2-deoxy- A -D-glucopyranoside (3.65g, 10 mmol) dissolved in dichloromethane and cooled down to 10 degrees. After adding 30 ml of 1N potassium carbonate aqueous solution, the mixture was stirred at room temperature for 3 hours, and the mixture was separated and dried over anhydrous sodium sulfate. The organic phase is concentrated to dry column to obtain thymolphthalein-N-acetyl-3,4,6-O-triacetyl-beta-D-glucapyranoside (Yield 4.5 g, yield 61.2%).

As the paragraph descriping shows that 125-20-2 is playing an increasingly important role.

Reference£º
Patent; Guangdong Younide Biological Technology Co., Ltd.; Sai Chi Bio-technology (Shanghai) Co., Ltd.; Su Hongwen; Lai Hua; Liang Weiye; Liu Zhiwen; (6 pag.)CN108218926; (2018); A;,
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90843-31-5, 5-Acetyl-2,3-dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-[1-(3-Bromo-phenyl)-vinyl]-2,3-dihydro-benzofuran A 1.6 M solution of n-butyllithium in hexane (22.3 mL, 35.7 mmol, 1.16 eq.) was added dropwise to a solution of 1,3-dibromobenzene (8.0 g, 33.9 mmol, 1.1 eq) in 30 mL of dry tetrahydrofuran at -78 C. under nitrogen, and the mixture was stirred for 20 min. After this time, a solution of 1-(2,3-dihydro-benzofuran-5-yl)-ethanone (5.0 g, 30.8 mmol, 1.0 eq, prepared as shown in Scheme 4) in 20 mL of dry tetrahydrofuran was added over 10 minutes and the resulting solution was further stirred for 45 min. The reaction mixture was examined LCMS which showed complete conversion to the desired product. 20 mL of a saturated aqueous solution of ammonium chloride was added and the cooling bath was removed. The mixture was poured into 100 mL of a 1:1 diisopropyl ether/water mixture. The organic fraction was dried over sodium sulfate and concentrated to give a yellow oil. The oil was dissolved in 10 mL of acetic acid. 0.3 mL of 98% sulfuric acid were added and the dark solution was stirred at room temperature. After 30 min LCMS showed complete conversion to the desired product. Crushed ice was poured in the reaction mixture which was then extracted with dichloromethane. The organic fraction was collected, washed with water, sodium baicarbonate solution and dried with over sodium sulfate. The crude product was purified by flash chromatography eluding with cyclohexane. 3.5 g of clean product was obtained as colorless liquid (yield: 38%) Mass (calculated) C16H13BrO [301]; (found) [M+H+]=302 LC Rt=2.97 min (5 min method) 92%

The synthetic route of 90843-31-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Andreini, Matteo; Gabellieri, Emanuele; Guba, Wolfgang; Marconi, Guido; Narquizian, Robert; Power, Eoin; Travagli, Massimiliano; Woltering, Thomas; Wostl, Wolfgang; US2009/209529; (2009); A1;,
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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.

Example 17 4-(Benzofuran-2-ylmethoxy)-2-(2,6-dioxo-piperidin-3-yl)-isoindole-l,3-dioneStep 1 :[211] 2-Benzofurancarbaldehyde (2.2 g, 15 mmol) was dissolved in 25 mL of methanol. To this solution was added sodium borohydride (0.28 g, 7.5 mmol) in small portions over a period of 20 minutes. Then 2 mL of water were added and the mixture was evaporated. The residue was dissolved in ethyl acetate (75 mL) and washed with water (3 x 75 mL), dried (MgSO4) and evaporated, providing 2.1 g of benzofuran-2-yl-methanol, in 95% yield; 1H NMR (CDCl3) delta 2.03 (t, J = 6.1 Hz, IH), 4.77 (d, J = 6.1 Hz, 2H), 6.66 (s, IH), 7.19-7.32 (m, 2H), 7.45-7.50 (m, IH), 7.53-7.57 (m, IH).

As the paragraph descriping shows that 4265-16-1 is playing an increasingly important role.

Reference£º
Patent; CELGENE CORPORATION; WO2008/115516; (2008); A2;,
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13391-28-1, 5-Methoxybenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

j0379j 2.5 M n-butyllithium in hexanes (2.8 mE, 7.00 mmol) was added slowly to a solution of 5-methoxy-i-benzofuran(1.0 g, 6.75 mmol) in dry tetrahydrothran (15 mL) at -78 C under a nitrogen atmosphere. After 1 hour stirring at -78 C, triisopropylborate (3.12 mL, 13.5 mmol) was added drop-wise and the mixture stirred for 30 minutes at -78 C. The dry ice bath was removed, 2 M aqueous hydrochloric acid (20 mL) was added and the mixture warmed to room temperature whilst stirring overnight. The reaction mixture was poured into waler (25 mL) and extracted with diethyl ether (3 x 20 mL). The combined organics were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. Dichloromethane (20 mL) was added and the mixture sonicated for 10 minutes. The minimum amount of methanol (ca. 1 mL) was added to ffilly dissolve the solids and the solution sonicaled for 10 minutes. Heptane (20 mL) was added and the precipitated solids collected by vacuum filtration and allowed to dry under vacuum for 2 hours to give the title compound 476 mg (37% yield) as a white solid. On NMR (500 MHz, DMSO) 8.53 (s, 2H), 7.46 (d, J= 8.94 Hz, IH), 7.39 (s, lH), 7.19 (d, J= 2.51 Hz, 1H), 6.93 (dd, J= 2.60,8.92 Hz, 1H), 3.78 (s, 3H).

13391-28-1 5-Methoxybenzofuran 25943, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; KISELYOV, Alex; BROWN, Christopher, John; GALAN, Sebastien, Rene Gabriel; PRIME, Michael, Edward; GILES, Paul, Richard; GADOULEAU, Elise, Luciennen Paulette; KRUeLLE, Thomas, Martin; CLARK-FREW, Daniel; JOHNSON, Peter, David; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; COE, Samuel; HAYES, Sarah; (271 pag.)WO2016/33445; (2016); A1;,
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