Category: benzofuran

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.

EXAMPLE 1 Synthesis of (3’R,4’S,5’R)-6″-chloro-4′-(3-chloro-2-fluorophenyl)-N-(4-((4-(2-((2-(2,6- dioxopiperidin-3-yl)-l,3-dioxoisoindolin-4-yl)oxy)acetamido)butyl)carbamoyl)phenyl)- 2″-oxodispiro[cyclohexane-l,2′-pyrrolidine-3′,3″-indoline]-5′-carboxamide Ste 1 : Synthesis of S 1 To a round-bottom flask, 3-hydroxyphthalic anhydride (1 g, 6.09 mmol) and 3-aminoperidine-2,6-dione hydrochloride (1.0 g, 6.09 mmol) were mixed in 50 mL of toluene. Triethyl amine (0.93 mL, 6.7 mmol) was added. The resulting reaction mixture was heated to reflux for 12 h with Dean-Stark Trap equipment. After cooling to ambient temperature, evaporation of most of the solvent to give a crude product, which was purified by flash column chromatography with DCM:EA to get the desired product as a slightly yellow solid S I (1.5g, 90% yield). 1H NMR (400 MHz, DMSO-d6) delta (ppm) 11.16 (s, 1H), 11.08 (s, 1H), 7.65 (t, = 7.6 Hz, 1H), 7.32 (d, = 7.2 Hz, 1H), 7.25 (d, = 8.4 Hz, 1H), 5.07 (dd, = 12.8 Hz, = 5.2 Hz, 1H), 2.93-2.84 (m, 1H), 2.61-2.46 (m, 1H), 2.05-2.01 (m, 1H)., 37418-88-5

37418-88-5 4-Hydroxyisobenzofuran-1,3-dione 96580, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; LI, Yangbing; AGUILAR, Angelo; ZHOU, Bing; HU, Jiantao; XU, Fuming; QIN, Chong; HU, Yang; XIANG, Weiguo; REJ, Rohan; YANG, Jiuling; HAN, Xin; BAI, Longchuan; YANG, Chao-Yie; (252 pag.)WO2017/176958; (2017); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.123654-26-2,4-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid,as a common compound, the synthetic route is as follows.

a) A mixture of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxylic acid (4.3 g) in thionyl chloride (100 ml) and CHCl3 (200 ml) was stirred and refluxed for 2 hours. The mixture was cooled and the solvent was evaporated. Toluene was added and evaporated again, yielding 4.8 g of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarbonyl chloride (100% crude residue) (intermediate 7).

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; Janssen Pharmaceutica, N.V.; US5872131; (1999); A;,
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.64169-34-2,5-Bromoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

Method 0 : 4-bromo-2- (hydroxymethyl) -N- (2,2,2- trifluoroethyl) benzamide; [00134] To a stirred suspension of aluminium trichloride (4.07 g, 30.5 mmol) in dichloroethane (60 ml) cooled to 5C under a nitrogen atmosphere was added the solution of trifluoroethylamine (5.84 g, 38.7 mmol) at such a rate to keep the temperature of the reaction mixture below 100C. After complete addition the reaction mixture was allowed to warm up to room temperature and stirred at this temperature for 4 hours. After this time bromophthalide powder (5 g, 23.5 mmol) was added in one portion and the reaction mixture was then heated to 800C for 18 hours. TLC showed complete conversion from starting material to product and the reaction was carefully quenched with iced water (100 ml) and stirred for 30 minutes until all the ice melted. Dichloromethane was added and the mixture was filtered through a pad of silica and washed with copious amounts of DCM to remove the aluminium residues. The filtrate was separated and the aqueous layer was further extracted with DCM (2 x 100 ml) . The organic layers were combined and dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound as an off-white powder (3.37 g, 46% yield) . 1H NMR (DMSO D6, 400 MHz) 4.02-4.11 (2H, m) , 4.60-4.61 (2H, m) , 5.43- 5.46 (H, m) , 7.36-7.39 (H, d) , 7.55-7.57 (H, m) , 7.76 (H, s) and 9.09-9.12 (H, m) ; MS (ES+) 312, (ES”) 310., 64169-34-2

The synthetic route of 64169-34-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/128009; (2008); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.271-89-6,Benzofuran,as a common compound, the synthetic route is as follows.

General procedure: To a solution of anisole 3A (3.0 mmol, 324.4 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol,1.55 M in hexane, 2.87 mL) at 0 C. The mixture was stirred for 2 h at 0 C under an argon atmosphere. Then, pivalonitrile (9.0 mmol, 748.2 mg) in THF (2.0 mL) was added to the mixture at 0 C and the obtained mixture was stirred for 30 min in the temperature range of 0 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 2-methoxybenzonitrile 2A (315.6 mg, 79%)., 271-89-6

As the paragraph descriping shows that 271-89-6 is playing an increasingly important role.

Reference£º
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
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4265-25-2, 2-Methylbenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-Methylbenzofuran (400 mg, 3.03 mmol) was dissolved in tetrahydrofuran (15 mL), cooled to -78C, and lithium diisopropylamide (2 M tetrahydrofuran solution, 1.7 mL, 3.33 mmol) was added dropwise. The reaction solution was stirred at -78C for 1 hour, and 1-bromo-3-chloropropane (525 mg, 3.33 mmol) was added and the mixture was stirred at -78C for another 2 hours. The reaction was quenched by the addition of saturated ammonium chloride solution (30 mL). The mixture was extracted with ethyl acetate (30 mL x 2). The organic phases were combined, washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to give 2-(4-chlorobutyl)benzofuran (500 mg, as ayellow oil). MS-ESI M + H]+ calcd. 209, found 209.

4265-25-2, The synthetic route of 4265-25-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Lingyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (160 pag.)EP3299371; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.28281-76-7,5-Methoxyisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

28281-76-7, Triphenylphosphine (1.3 g, 5.1 mmol) was dissolved in 6 ml of THF, which was cooled down to 0 C. under nitrogen gas. THF (5.0 ml) solution containing CBr4 (0.84 g, 2.5 mmol) dissolved therein was added thereto, followed by stirring until the color of the solution turned yellow. After the color change, TEA (0.91 ml, 5.1 mmol) was added drop by drop for 5 minutes, to which THF (1 ml) solution containing the compound prepared in step 4 above (0.15 g, 0.85 mmol) dissolved therein was added gradually. The reaction solution was stirred at 0 C. for 30 minutes. Then, the temperature of the reaction solution was adjusted to room temperature, followed by stirring for overnight. The reaction was quenched with a saturated NH4Cl aqueous solution. When the phases were separated, the water layer was extracted by using hexane. The combined organic layer was concentrated under reduced pressure. The obtained residue was dissolved in ethoxyethane and filtered through a celite pad. The obtained solution was concentrated by rotary evaporation and purified by flash column chromatography. As a result, a target compound was obtained (0.077 g, 27%). NMR graphs of the obtained target compound are shown in . The upper graph of is a graph showing the results of 1H NMR of Example 7, and the lower graph of is a graph showing the results of 13C NMR of Example 7. 1H NMR (DMSO-d6, 500 MHz) delta 7.91 (d, J=8.5 Hz, 1H), 7.76 (s, 1H), 7.32 (d, J=7.0 Hz, 1H), 3.93 (s, 3H). 13C NMR (DMSO-d6, 125 MHz) delta 165.0, 163.5, 145.1, 138.2, 127.9, 118.2, 117.5, 108.2, 77.4, 56.2.

As the paragraph descriping shows that 28281-76-7 is playing an increasingly important role.

Reference£º
Patent; SEOUL NATIONAL UNIVERSITY R&DB FOUNDATION; Kim, Byeong Moon; Choi, Bong Kyu; Sim, Jae Hyun; Ryu, Eun Ju; Park, Ji Su; Bae, Il Hak; (54 pag.)US2019/345126; (2019); A1;,
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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

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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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.,700-85-6

To a solution of 5-fluoro-3H-isobenzofuran-1-one (1.00 g, 6.57 mmol) in DMF (5 ml) was25 added CH3I (0.82 ml, 13.1 mmol) at -20C followed by addition of NaH (0.34 g, 7.89mmol) portion wise. The reaction mixture was stirred at room temperature for 3h. Progressof the reaction was monitored by TLC and LCMS. After completion, the reaction mixturewas diluted with ice-cold saturated aqueous NH4CI solution (50 ml) and extracted withEtOAc (2 x 30 ml). The organic layer was separated, dried over anhydrous Na2S04 and30 concentrated under vacuum. The crude obtained was purified by combi-flash columnX-~chromatography (4% EtOAc in hexanes) to afford 5-fluoro-3-methyi-3H-isobenzofuran-1-one X-27a (0.44 g) an as an off-white solid.Yield: 35%Basic LCMS Method 2 (ES+): 167 (M+H)+, 87 % purity.5 1H NMR (400 MHz, DMSO-d5) o 1.56 (d, J=6.36 Hz, 3H) 5.68 (q, J=6.36 Hz, 1 H) 7.41-7.48 (m, 1 H) 7.62 (dd, J=8.80, 1.96 Hz, 1 H) 7.87-7.93 (m, 1 H).

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

Reference£º
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.82104-74-3,1-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile,as a common compound, the synthetic route is as follows.

82104-74-3, 1048g of a 10percent solution of 4-fluorophenylmagnesium bromide in tetrahydrofuran are added to a suspension of 60.Og of 5-cyanophthalide in 390ml of 1 ,2-dimethoxyethane at -100C within three hours. After stirring for 30 minutes at -100C, the cold reaction mixture is poured into 1L of aqueous NH4CI (18Og in 1000ml of water, 200C) in about 5 minutes. The layers are separated and the aqueous layer is extracted with 300ml of tetrahydrofuran. The organic layers are combined and volatiles are removed under reduced pressure at 45¡ãC. The residue is dissolved in a mixture of 100OmL of CH2CI2 and 200ml of water containing 2.5g of sodium carbonate (pH of 9). The layers are separated and the organic phase is dried with 4Og of sodium carbonate. The dry CH2CI2 solution is treated with 6g of charcoal, stirred for 10 minutes and the charcoal is removed by filtration. The filter cake is washed with 5OmL of CH2CI2. Filtrate and washing liquid are combined and the solvent is removed under reduced pressure. 30OmL of diisopropylether are added to the residue. After stirring for 1 hour at 22¡ãC the crystal suspension is cooled to 0¡ãC and stirred for another two hours, then cooled to -100C and stirred for 14 hours. The product is isolated by filtration and washed with 4OmL of chilled diisopropylether, 8OmL of a 1 :1 mixture of diisopropylether/cyclohexane and 8OmL of cyclohexane. After drying for 3 hours at 50¡ãC in vacuo 83.0 g (86.2 percent of theory, purity (HPLC): 99.8 areapercent) white, crystalline powder of the title compound are obtained (mp. 85¡ãC).1H-NMR (CDCI3, 300MHz): delta 3.01 (t, J = 6.30, 0.8 H, OH), 3.66 (s, 0.2 H, OH), 4.66 (d, J = 6.11 Hz, 1.6 H, CH2-O), 5.33 (m, CH2-O, 0.4 H, lactol-isomer), 7.03 – 7.93 (m, 7 H, ArH)

The synthetic route of 82104-74-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SANDOZ AG; WO2007/82771; (2007); 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.127264-14-6,5-(2-Bromoethyl)-2,3-dihydrobenzofuran,as a common compound, the synthetic route is as follows.

Preparation 28 Preparation of N-{2-(2,3-dihydrobenzofuran-5-yl)ethyl}methylamine A solution of 5-(2-bromoethyl)-2,3-dihydrobenzofuran (1.5 g – see Preparation 20) in 33percent methylamine in methanol (40 ml) was heated at 100¡ãC in a stainless steel pressure vessel for 6 hours then concentrated in vacuo . The residue was partitioned between dichloromethane (50 ml) and 10percent aqueous sodium carbonate (50 ml). The layers where separated and the aqueous layer was further extracted with dichloromethane (2 * 50 ml). The aqueous layer was concentrated in vacuo to give a solid which was triturated with boiling 2-propanol. The mixture was filtered and the filtrate concentrated in vacuo to give a solid which was purified by column chromatography on silica eluding with dichloromethane containing methanol (0percent up to 1percent). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless solid, yield, 0.31 g, m.p. 153-155¡ãC. 1H N.m.r. (CDCl3) delta = 9.80-9.60 (brs, 1H), 7.10 (s, 1H), 7.00-6.95 (d, 1H), 6.75-6.70 (d, 1H), 4.60-4.50 (t, 2H), 3.30-3.10 (m, 6H), 2.75 (s, 3H) ppm., 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; Pfizer Limited; PFIZER INC.; EP364123; (1991); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem