Heterocyclic Building Block-benzofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.42933-43-7,2,3-Dihydrobenzofuran-5-amine,as a common compound, the synthetic route is as follows.

General procedure: Compound 18 (0.695 g, 5 mmol) and NaH (60percent dispersed inmineral oil, 0.12 g, 7.5 mmol) were dissolved in THF at 0?5 C. Tothis solution CH3I (1.06 g, 7.5 mmol) was added, and the mixturewas stirred at 0?5 C for an additional 3 h. The reaction mixturewas carefully quenched with water and was diluted with EtOAcand water. The organic layer was separated and washed with water(2 10 mL). After drying with anhydrous Na2SO4, the organic solventwas concentrated in a rotary evaporator to <1 mL. This residuewas placed on top of a silica gel column and eluted withhexane and EtOAc. Fractions containing the product (TLC) werepooled and evaporated to afford a yellow oil, compound 19, in75percent yield. Compound 23 was synthesized from 22, following the procedureof 19, and it was obtained as an off-white solid in 68percent yield.The color of this compound slowly turned dark when exposed toair, and it was directly used for the next step. mp 118.3?121.3 C;TLC Rf 0.47 (hexanes: EtOAc, 3:1); 1H NMR (CDCl3) d 2.82 (s, 3H,NCH3), 3.18 (t, J = 8.56 Hz, 2H, CH2), 3.43 (br, 1H, exch, NH), 4.50 (t, J= 8.58 Hz, 2H, CH2), 6.42 (dd, J = 2.47 Hz, 8.43 Hz, 1H, ArH), 6.58 (d, J= 2.25 Hz, 1H, ArH), 6.67 (d, J = 8.43 Hz, 1H, ArH); ESIMS m/z [M+H]+,calcd 150.08, found 150.09. 42933-43-7 2,3-Dihydrobenzofuran-5-amine 3841102, abenzofuran compound, is more and more widely used in various. Reference£º
Article; Xiang, Weiguo; Choudhary, Shruti; Hamel, Ernest; Mooberry, Susan L.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2437 – 2451;,
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10242-12-3, 5-Nitrobenzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 177 (342 mg, 1.649 mmol) and compound 175 (287 mg, 1.269 mmol) were dissolved in DMF (10 mL). EDC (316 mg, 1.649 mmol) and DMAP (77 mg, 0.634 mmol) were added and the reaction was stirred under Ar at rt overnight. The crude reaction mixture was directly purified by silica gel chromatography to yield compound 178 (63 mg, 12% yield). LCMS = 4.74 mm (8 mm method). Mass observed (ESI): 415.9 (M+H). ?H NMR (400 MHz, DMSO-d6): 2.60 (t, J= 6.7 Hz, 2H), 3.50 (q, J= 6.5 Hz, 2H), 3.62 (s, 3H), 3.97 (s, 3H), 7.62 (s, 1H), 7.96 (d, J= 9.1 Hz, 1H), 8.02 (t, J= 6.1 Hz, 1H), 8.07 (s, 1H), 8.35 (dd, J= 9.1, 2.5 Hz, 1H), 8.83 (d, J= 2.4 Hz, 1H), 11.30 (s, 1H).

The synthetic route of 10242-12-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; CHARI, Ravi, V.J.; (312 pag.)WO2019/133652; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15832-09-4,6-Methoxy-3(2H)-benzofuranone,as a common compound, the synthetic route is as follows.

To a solution of 2-12 (450 mg, 2.74 mmol) in anhydrous acetic acid (4.9 ml/mmol) was added the 3-chloro-4-hydroxybenzaldehyde (2.74 mmol), followed by dropwise addition of concentrated HCl (0.3 ml/mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with distilled water (100 ml) and stirred for 15 min. The precipitate formed was filtered under suction to yield aurone 6-12 which was used without further purification, yellow solid, yield 91.6%. M.p. 210-212 C, 1H NMR (DMSO-d6, 500 MHz): delta 8.0 (d,J 2 Hz, 1H), d 7.79 (dd, J1 2 Hz, J2 8.6 Hz, 1H), 7.68 (d,J 8.6 Hz, 1H), 7.17 (d, J 2 Hz, 1H), 7.08 (d, J 8.5 Hz, 1H), 6.85 (dd,J1 2.1, J2 8.5 Hz, 1H), 6.79 (s, 1H), 3.93 (s, 3H).

The synthetic route of 15832-09-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liew, Kok-Fui; Chan, Kit-Lam; Lee, Chong-Yew; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 195 – 210;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.89877-62-3,3-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile,as a common compound, the synthetic route is as follows.

1-Bromo-6-cyanophthalide (65) 6-Cyanophthalide (64, 2.73 g, 17.2 mmol) was dissolved in carbon tetrachloride (120 mL). 3-Chloroperbenzoic acid (100 mg) and N-bromosuccinimide (3.20 g, 17.9 mmol) were added. Light was applied with a 250 W lamp and the reaction mixture was heated at reflux for 24 h. The solvent was removed and the residue purified by silica gel column chromatography, eluting with ethyl acetate-hexane, 1:7. The product was obtained as a white solid (2.32 g, 56.7%): mp 132-134 C. IR (Film) 3090, 3064, 3032, 2992, 2235, 1788, 1738, 1428, 1295, 1227, 1119, 990, 717, 664 cm-1; NMR (300 MHz, CDCl3) delta 8.23 (s, 1H), 8.05 (dd, J=1.1 Hz, J=8.1 Hz, 1H), 7.79 (d, J=7.9 Hz, 1H), 7.44 (s, 1H); 13C NMR (75 MHz, CDCl3) delta 165.1, 152.2, 138.3, 130.0, 125.0, 121.5, 116.8, 115.3, 73.4; CIMS m/z (rel intensity) 238 (MH+, 13), 160 [(MH-Br)+, 100].

The synthetic route of 89877-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CUSHMAN, MARK S.; NGUYEN, TRUNG X.; CONDA-SHERIDAN, MARTIN M.; US2013/345252; (2013); A1;,
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28281-76-7, 5-Methoxyisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 4-methoxyphthalic anhydride (27.8 g, 0.16 mol) and formamide (175 ml) was stirred and held at 2100C for 5 hours and was then allowed to cool to room temperature overnight. The solid material was filtered off, washed sequentially with water (100 ml), 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford A- methoxyphthalimide (21.3 g, 77%) as a pale yellow solid. 1H NMR (DMSOd6) 11.15 (1 H, br s), 7.74 (1H, d), 7.33-7.28 (2H, m), 3.92 (3H1 s).

28281-76-7 5-Methoxyisobenzofuran-1,3-dione 639748, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); 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.588703-29-1,Methyl benzofuran-6-carboxylate,as a common compound, the synthetic route is as follows.

5.Add compounds to the reaction flask1 (5.89kg, 11.04mol, 1.0eq) and MeOH (30L),Dissolve with stirring, add 27.65% NaOH aqueous solution to the reaction solution(9L), stirred at room temperature for 1 hour, TLC analysis of raw materials was consumed.Dilute the reaction solution with 20L of water.Wash the reaction with 20L of DCM.The aqueous phase is adjusted to a pH of 2 to 3 using concentrated hydrochloric acid, and the solid content is filtered.Dry at 45 to obtain white solid compound(2.66 kg, yield: 33%).

588703-29-1 Methyl benzofuran-6-carboxylate 22481705, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; Shanghai Haoyuan Pharmaceutical Co., Ltd.; Zheng Baofu; Gao Qiang; Li Shuoliang; Yang Chengwu; Ma Zhenbiao; (11 pag.)CN110684000; (2020); A;,
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496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Part A Preparation of 5-(2,3-dihydrobenzofuranyl) sulfonyl chloride To a solution of 3.35 g of anhydrous N,N-dimethylformamide at 0 C. under nitrogen was added 6.18 g of sulfuryl chloride, whereupon a solid formed. After stirring for 15 minutes, 4.69 g of 2,3-dihydrobenzofuran was added, and the mixture heated at 100 C. for 2 hours. The reaction was cooled, poured into ice water, extracted with methylene chloride, dried over magnesium sulfate, filtered and concentrated the crude material. This was recrystallized from ethyl acetate to afford 2.45 g of 5-(2,3-dihydrobenzofuranyl)sulfonyl chloride.

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; G.D. Searle & Co.; US5705500; (1998); A;; ; Patent; G.D. Searle & Co.; US5776971; (1998); A;; ; Patent; G.D. Searle & Co.; US6143788; (2000); A;,
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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.23145-07-5,5-Bromobenzofuran,as a common compound, the synthetic route is as follows.

Under a nitrogen stream, 5-bromobenzofuran (25 g, 0.126 mol), 4,4,4 ‘, 4,5,5,5,5-octamethyl-2,2’-bi (1,3,2-dioxaborolane) (38.67 g, 0.152 Dioxane (500 ml), and the mixture was stirred at 130 C for 12 hours. The reaction was terminated. The mixture was extracted with ethyl acetate, the water was removed with MgSO 4 and purified by column chromatography to obtain 23.23 g of benzofuran-5-yl) -4,4,5,5-etramethyl-1,3,2-dioxaborolane , Yield: 75%).

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

Reference£º
Patent; Doosan Co., ltd; Kim, Tae Hyoung; Kim, Song Mu; Lee, Chang Jun; Sin, Jin Yong; Baek, Young Mi; Park, Ho Chul; (40 pag.)KR101599586; (2016); B1;,
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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.128851-73-0,6-Bromobenzofuran,as a common compound, the synthetic route is as follows.

j0041 1j To a solution of 6-bromobenzofuran (1.0 g, 5.1 mmol) in anhydrous tetrahydrofuran (15 mL) at -78 C under nitrogen was added dropwise lithium diisopropylamide (2.0 M in n-heptane, 3.1 mL, 6.2 mmol). The mixture was stirred at at -78 C for 30mm and then hexachloroethane (1.2 g, 5.1 mmol) was added dropwise. The reaction was stirred at -78 C for another one hour, then poured into water (20 mL) and extracted with ethyl acetate (2 x 30 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 1:01 to give compound B-70 (0.36 g, 28% yield) as a colorless oil. ?H-NMR (CD3OD, 400 MHz): 7.69 (s, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.40 (dd, J1=8.4 Hz, J2=1.6 Hz, 1H), 6.77 (s, 1H).

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Reference£º
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

32703-79-0, 5-(tert-Butyl)isobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A solution of substituted benzyl amine (10 mmol) and an acid anhydride (10 mmol) in glacial acetic acid (15mL) was heated under reflux for 4h. After the evaporation of the reaction mixture to dryness under reduced pressure, the residue was neutralised by a solution of sodium bicarbonate (4%) until effervescence ceased. The precipitate obtained was washed with water, dried and re-crystallised from an appropriate solvent.

32703-79-0 5-(tert-Butyl)isobenzofuran-1,3-dione 122930, abenzofuran compound, is more and more widely used in various.

Reference£º
Article; Alanazi, Amer M.; El-Azab, Adel S.; Al-Suwaidan, Ibrahim A.; Eltahir, Kamal Eldin H.; Asiri, Yousif A.; Abdel-Aziz, Naglaa I.; Abdel-Aziz, Alaa A.-M.; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 115 – 123;,
Benzofuran – Wikipedia
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