Heterocyclic Building Block-benzofuran

174775-48-5, Ethyl 5-aminobenzofuran-2-carboxylate is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Commercially available ethyl 5-NITROBENZOFURAN-2-CARBOXYLATE 30 was HYDROGENATED on PD-C and ACYLATED using commercially available 4-NITRO-N-METHYL-2- TRICHLOROACETYL-PYRROLE 32 to form 33. HYDROGENATION of 33 followed by acylation with 32 afforded the nitro compound 35, which upon HYDROGENATION yielded 36 as the amino compound. ACETYLATION of the amino group of 36 followed by base catalyzed hydrolysis resulted in the acid 37. Coupling of 37 with the hydrochloride salt 39 (obtained by DEPROTECTION of the BOC derivative 38) using EDC afforded the ester 40. See Figure 4., 174775-48-5

As the paragraph descriping shows that 174775-48-5 is playing an increasingly important role.

Reference£º
Patent; THE GOVERNMENT OF THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; WO2005/32594; (2005); A2;,
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7168-85-6, 7-Methoxybenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a round bottom flask containing 7-methoxybenzofuran (2.45 g, 16.5 mmol) and anhydrous DCM (25 mL) was carefully added a solution of boron tribromide in DCM (1 M, 33 mL) at 0 C. The reaction was allowed to warm to rt and stir at rt for 4 h. The reaction was quenched with water (20 mL), extracted with Et^O, concentrated to dryness, and purified by flash column chromatography to yield the title compound (1.23 g, 55% yield) as a light-brown oil. MS (ESI): mass calcd. for C8H602, 134.0.1; m/z found, 135.1 [M+H]+., 7168-85-6

As the paragraph descriping shows that 7168-85-6 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (1000 pag.)WO2017/100668; (2017); A1;,
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641-70-3, 3-Nitrophthalic anhydride is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,641-70-3

Example 2A4-Nitroisobenzofuran- 1 (3H)-one[00471] A suspension of sodium borohydride (0.757 g, 20 mmol) in anhydrous tetrahydrofuran (120 mL) was cooled to 0 C. A solution of 4-nitrobenzofuran-l,3-dione (6.18 g, 32 mmol) in anhydrous tetrahydrofuran (30 mL) was then added dropwise to the suspension. After the addition, the mixture was allowed to stir at this temperature for 3 hr. The reaction was quenched with 3N hydrochloric acid (to pH=l). Water (40 mL) was added to the mixture and stirred for 1 hr. Tetrahydrofuran was removed under reduced pressure. The residue was partioned between water (150 mL) and ethyl acetate (150 mL*3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether / ethyl acetate = 20: 1 to 2: 1) to give 4-nitroisobenzofuran- 1 (3H)-one (4.2 g, yield 73%) as a white solid. MS (ESI) m/z: 180(M+1)+. ^-NMR (400MHz, CDC13) delta 5.77 (s, 3H), 7.32-7.34 (d, J=8.4 Hz, 1H), 7.81-7.85 (t, J= 8.0 Hz, 1H), 8.29 (d, J= 8.0 Hz, 1H), 8.55 (d, J= 8.0 Hz, 1H).

641-70-3 3-Nitrophthalic anhydride 21631, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; WO2011/130661; (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.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.

69999-16-2, EXAMPLE 5 2-(2,3-Dihydro-5-benzofuranyl)malonic acid To a solution of diisopropylamide (20 mmole) in 50 ml of anhydrous tetrahydrofuran (THF) maintained under a nitrogen atmosphere at -40 C. is added n-butyllithium (20 mmole). The mixture is stirred for 15 minutes and then (2,3-dihydro-5-benzofuranyl)acetic acid (10 mmole) is added. The mixture is heated at 50 C. for 1 hour and then cooled to -70 C. and ethyl chloroformate (10 mmole) is added. The temperature is increased and the mixture is stirred for about 20 minutes. The mixture is poured over ice and hydrochloric acid. The aqueous phase is extracted with ether. The ether extracts are combined, dried and evaporated to give 2-(2,3-dihydro-5-benzofuranyl)malonic acid, monoethyl ester.

69999-16-2 2,3-Dihydrobenzofuranyl-5-acetic acid 2737455, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Richardson-Merrell Inc.; US4138397; (1979); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.115010-11-2,2,3-Dihydro-1-benzofuran-5-sulfonoylchloride,as a common compound, the synthetic route is as follows.

Take compound IX-2 (300mg, 1.37mmol) in chlorobenzene (2mL),Add N-bromosuccinimide (244 mg, 1.37 mmol),Azobisisobutyronitrile (3mg),The temperature was raised to 80 C.After heating for 1.5 hours,Add N-bromosuccinimide (122 mg, 0.685 mmol),The reaction was monitored by TLC after 4 hours.After the reaction was cooled to room temperature, water (5 mL) was added.Ethyl acetate extraction (3mL x 3),Combined organic phases,Washed with saturated saline (3mL x 2),Dry over anhydrous sodium sulfate.The solvent was distilled off under reduced pressure,The residue was purified by column chromatography (petroleum ether / ethyl acetate = 50/1) to obtain compound XI-1 (yellow oil, 337 mg).

115010-11-2, 115010-11-2 2,3-Dihydro-1-benzofuran-5-sulfonoylchloride 2776154, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; China Pharmaceutical University; Sun Hongbin; Yan Dingfei; Feng Zhiqi; Zhang Jia; Yao Zhiying; Zhao Wenfeng; Zhang Xiangying; Sun Geng; Han Lishuai; Wu Wenzhen; Liu Shengjie; Zhao Xing; Li Minglei; Yu Shengqi; Chen Hui; Cheng Yalong; Wang Pengfei; Dai Liang; Wen Xiaoan; Liu Jun; (102 pag.)CN110372638; (2019); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1083168-69-7,(2,3-Dihydrobenzofuran-6-yl)methanol,as a common compound, the synthetic route is as follows.

Step g: 6-(Chloromethyl)-2,3-dihydrobenzofuran; To a solution of (2,3-dihydrobenzofuran-6-yl)methanol (13.8 g, 92mmol) inCHCl3 (200 mL) was slowly added SOCl2 at 0C. The reaction mixture was stirred at reflux for 4h. After the solvent was removed, saturated NaHCO3 and ethyl acetate were added to the mixture. The organic layer was extracted with ethyl acetate. The combined organic layer was then washed with brine and dried over Na2SO4, filtered and concentrated to afford 6- (chloromethyl)-2,3-dihydrobenzofuran (12.3 g, 80.0% yield). 1H NMR (400 MHz, CDCl3) delta: 7.16 (d, J= 7.5, IH), 6.87 (d, J= 7.5, IH), 6.83 (s, IH), 4.58 (t, J= 8.7, 2H), 4.49 (s, 2H), 3.20 (t, J= 8.7, 2H)., 1083168-69-7

1083168-69-7 (2,3-Dihydrobenzofuran-6-yl)methanol 18356898, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/141119; (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.37418-88-5,4-Hydroxyisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

4-Hydroxyisobenzofuran-l,3-dione (3.6 g, 22mmol), 3-aminopiperidine-2,6-dione (3.6 g, 22mmol) and KOAc (8.6 g, 88 mmol) were dissolved in acetic acid (70 mL). The reaction mixture was stirred at 120 C for 1 hour then cooled and diluted with water (100 mL). The resulting mixture was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with NaHC03 and brine, dried (Na2S04) and filtered. The solvents were removed and the solid dried under vacuum to give the title compound (4.0 g, 67% yield) as a blue solid. 1H NMR (400 MHz, DMSO): delta 11.30 (br s, 1H), 11.10 (s, 1H), 7.65 (dd, 1H), 7.30 (d, 1H), 7.24 (d, 1H), 5.07 (m, 1H), 2.87 (m, 1H), 2.53 (m, 2H), 2.02 (m, 1H)., 37418-88-5

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

Reference£º
Patent; CORNELL UNIVERSITY; DANA-FARBER CANCER INSTITUTE, INC.; CHILDREN’S MEDICAL CENTER CORPORATION; MELNICK, Ari, M.; GABAS, Lorena, Fontan; US, Ilkay; CASALENA, Gabriella; GRAY, Nathanael, S.; SCOTT, David, A.; HATCHER, John; DU, Guangyan; WU, Hao; QIAO, Qi; (157 pag.)WO2018/85247; (2018); A1;,
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82104-74-3, 1-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

82104-74-3, Example-1 a) Process for the preparation of citalopram (by single Grignard method) : A solution of 4-fluorophenyl magnesium bromide, prepared from 153.33g 4-flour bromobenzene (0.876 moles) and 25.33g magnesium turnings (1.055 moles) and Iodine (0.05g.) in 300mi of dry tetrahydrofuran was added to a suspension of 100g 5- cyanophthalide (0.628 moles) in 900moi dry toluene at-4 to-2¡ãC. After the reaction was completed, the reaction mass was quenched with 100moi 20percent aqueous ammonium chloride solution. Toluene layer was separated and diluted with 100ml of methanol. 12g Sodium borohydride (0. 324moles) was added over a period of one hour at 10-15¡ãC and the same temperature was maintained for additional one hour. The reaction mass was quenched with 200moi ice water and the toluene layer was separated. Toluene layer was washed with water (200ml) and then 10g of paratoluene sulphonic acid was added to toluene layer. The reaction mixture was heated to 80-85¡ãC and the temperature was maintained for additional 3 hours. After the completion of the reaction toluene layer was washed with aq. Sodium hydroxide solution (200ml), water (200moi) and dried over anhydrous sodium sulfate. The toluene solution was then added to a solution of 21grams of sodium hydride dissolved in 400ml of dimethyl sulfoxide and 500 ml toluene under nitrogen atmosphere at 20-25¡ãC. To the resulting solution a solution of 3-N, N,- dimethylaminopropylchloride (53g) in 200 ml of toluene was added quickly at 20-25¡ãC. The reaction mixture was stirred for 3 hrs at the same temperature. After completion the reaction the mixture was poured into ice water and the toluene layer was separated. The aqueous layer was extracted again with toluene. The combined toluene phase was extracted with 200moi 20percent aqueous acetic acid (40ml acetic acid and 160ml water). The aq. acid extract was cooled to 5-10¡ãC and the pH was adjusted to basic using liquor ammonia (85ml) at 5-10¡ãC and extracted with toluene 3x300m1. The toluene layer was washed with water and dried over anhydrous sodium sulphate. The toluene layer was treated with carbon (10g) and filtered. The filtrate toluene is subjected to salt formation as per following methods.; Example-2) Process for the preparation of citalopram (by double Grignard method): A solution of 4-fluorophenyl magnesium bromides prepared from 153. 33g 4-flour bromobenzene (0.876 moles) and 25.33g magnesium turnings (1. 055 moles) and iodine (0.05gm) in dry 300mi tetrahydrofuran was added to a suspension of 100g 5- cyanophthalide (0.628 moles) in 900ml dry methylene dichloride at-4 to-2¡ãC. After the completion of the reaction a solution of 3-N, N dimethylaminopropyl magnesiumchloride in toluen/THF mixture [generated in situ by reacting 175g 3-N, N dimethylamiopropyl chloride (1. 446mole) in 350ml toluene with 41. 6gm magnesium turnings (9. 733moles) and iodine (0. 05g) in dry 75ml tetrahydrofuran and dibromoethane] was added between 0- 5¡ãC. The reaction mass was then maintained at-5 to 0¡ãC for 3-4 hours. After completion of the reaction, the reaction mass was quenched with 200ml 20percent aqueous ammonium chloride solution. The toluene layer was separated and washed with 200ml water. Methylene dichloride and THF was distilled. 189g sulphuric acid and 60ml of water was added to the toluene layer and heated to 85-90¡ãC. The same temperature was maintained for additional 4-5 hours. After completion of the reaction the reaction mass was diluted with 200ml water and the pH was adjusted to basic with liquor ammonia below 10-15¡ãC. The toluene layer was separated, washed with 200moi water and extracted with 400ml 20percent acetic acid (80mi acetic acid and 320ml water). The aq. acid extract was cooled to 5- 10¡ãC and the pH was adjusted to 8.5 to 9.0 using liquor ammonia (85ml) at 5-10¡ãC and extracted with toluene 3x600m1. The toluene layer was washed with water, dried over anhydrous sodium sulphate. The dried toluene layer was treated with carbon (10g) and filtered. The filtrate toluene was subjected to salt formation in accordance with the following methods:

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

Reference£º
Patent; JUBILANT ORGANOSYS LIMITED; WO2005/77927; (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.230642-84-9,4-Vinyl-2,3-dihydrobenzofuran,as a common compound, the synthetic route is as follows.

To a flame-dried 1L three necked round bottom flask equipped with a magnetic stirrer was added N,N,2-trimethyl propionamide (17.8mL, 0.138mol) and anhydrous methylene chloride (200mL). The mixture was stirred to give a solution under argon and cooled to -15C. Trifluoromethanesulfonic anhydride (26mL, 0.154mol) was added via syringe and the resulting mixture was stirred at -15C for 10 minutes. A solution of [] (from Part D)(17.5g, 0.12mol), and collidine (21mL, 0.155mol) in anhydrous methylene chloride (30mL) was added at -15C. After the addition was completed, the reaction mixture was heated to reflux and stirred for 20 hours. The solvent was removed on a rotary evaporator and the residue oil was washed with ether (3x100mL) The residue was then dissolved in methylene chloride (150mL). Water (150mL) was added and the mixture was refluxed for 6 hours. After cooling to room temperature, the phases were separated. The aqueous layer was extracted with methylene chloride (2¡Á100mL). The rich organic layers were combined, washed with brine (200mL) and dried over anhydrous sodium sulfate. After removal of sodium sulfate by filtration, the filtrate was concentrated to give an oil which was purified by silica gel chromatography using 5-10% EtOAc/hexane as the eluent to give 19.0g (73%) title compound as a white crystalline compound. HPLC, 100A% at 220nm. 1H NMR (CDCl3) d, 7.14 (t, J=7.8Hz, 1H), 6.72 (t, J=8.2Hz, 2H), 4.52-4.65 (m, 2H), 3.50 (dd, J=7.0, 16.4Hz, 1H), 3.08-3.41 (m, 4H), 1.38 (s, 3H), 0.83 (s, 3H).

230642-84-9, The synthetic route of 230642-84-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; EP1041980; (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.1914-60-9,2,3-Dihydrobenzofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.

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

The synthetic route of 1914-60-9 has been constantly updated, and we look forward to future research findings.

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;,
Benzofuran – Wikipedia
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