Heterocyclic Building Block-benzofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10242-08-7,5-Methoxybenzofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.

To a stirred solution of tert-butyl (l -aminopiperidin-4-yl)carbamate (224 mg, 1 04 mmol, 1.0 equiv) in DMF (5 mL) was added HATU (790 mg, 2 08 mmol, 2.0 equiv) at RT and stirred for 10 minutes. Then 5-methoxybenzofuran-2 -carboxylic acid (200 mg, 1.04 mmol, 1.0 equiv) was added followed by the addition of DIPEA (0.6 ml,, 3.12 mmol, 3 0 equiv). The resulting reaction mixture was allowed to stir at RT for overnight. Product formation was confirmed by LCMS. the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (50 mL c 2). The combined organic layer was washed with water (30mL), brine solution (30 mL x 2), dried over anhydrous sodium sulfate and concentrated under reduced pressure, to obtain tert-butyl (l-(5-methoxybenzofuran-2-carboxamido)piperidin-4-yl)carbamate (300 mg, 74 % Yield) as an off white solid. LCMS 390.2 | M 1 1 | ; N .MR (400 MHz, DMSQ-tie) 6 9.62 (s, 1 H), 7.53 (d, .7=8 77 Hz, 1 H), 7.44 (s, 1 H), 7.24 (br s, 1 H), 6.97 – 7.08 (m, 1 H), 6 84 (d, .7=6 58 Hz, 1 H), 3.79 (s, 3 H), 3.23 (br s , 1 H), 2.95 (d, .7=10 09 Hz, 2 H), 2.62 – 2 81 (m, 2 H), 1.74 (d, 7=9.65 Hz, 2 H), 1.53 (d, ./ 10.52 Hz, 2 H), 1.38 (s, 9 H).

As the paragraph descriping shows that 10242-08-7 is playing an increasingly important role.

Reference£º
Patent; PRAXIS BIOTECH LLC; DELGADO OYARZO, Luz Marina; URETA DIAZ, Gonzalo Andres; PUJALA, Brahmam; PANPATIL, Dayanand; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; (0 pag.)WO2019/236710; (2019); 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.54008-77-4,2-Bromobenzofuran,as a common compound, the synthetic route is as follows.

General procedure: To a stirred solution of 2-bromobenzofuran/2-bromobenzo[b]thiophene (2.53 mmol) in ethanol (5 mL) was added hydrazine(0.08 g, 2.53 mmol), I2 (0.03 g, 10 mol%) and alkanone (2.53 mmol).The reaction mixture was reuxed for 1e3 h. After completion ofthe reaction as monitored by TLC, the reaction mixture wasquenched with a saturated aqueous solution of Na2S2O3. Theorganic and aqueous layers were then separated. The aqueous layerwas extracted with ethyl acetate (3 50 mL). The extract waswashed with water and nally with brine. The organic layer wasdried over anhydrous Na2SO4 and concentrated by rotary evapo-rator. Finally, the residue was puried by recrystallization from ethanol. 4.2.1. 2,3-Dimethyl-1H-benzofuro[2,3-b]pyrrole (4a)Yield 81% (376 mg); White solid; mp: 220e222C; IR (ATR,cm1): 3376 (NH);1H NMR (CDCl3, 400 MHz) d: 2.07 (s, 3H, CH3),2.30 (s, 3H, CH3), 5.00 (s, 1H, NH), 7.38 (t, 1H, J 7.6 Hz, Ar-H), 7.52(t, 1H, J 6.8 Hz, Ar-H), 7.69 (d, 1H, J 9.6 Hz, Ar-H), 7.90 (d, 1H, J 10 Hz, Ar-H) ppm;13C NMR (CDCl3, 100 MHz) d: 8.2, 11.7, 103.3,106.9, 112.1, 120.8, 123.2, 124.4, 127.3 (2C), 145.9, 157.2 ppm; LCMSm/z: [MH]Calcd for C12H12NO 186.08; Found 186.10; Anal. Calcdfor C12H11NO: C, 77.81; H, 5.99; N, 7.56. Found: C, 77.75; H, 5.90; N,7.51.

54008-77-4 2-Bromobenzofuran 2776264, abenzofuran compound, is more and more widely used in various.

Reference£º
Article; Chacko, Priya; Shivashankar, Kalegowda; Tetrahedron; vol. 74; 13; (2018); p. 1520 – 1526;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61090-37-7,2,3-Dihydrobenzofuran-4-amine,as a common compound, the synthetic route is as follows.

Place 4-amino-2,3-dihydrobenzofuran (405 mg, 3.0 mmol) in a round bottom flask,Concentrated sulfuric acid (450 muL, 8.3 mmol.) And 6.0 mL of deionized water were added to dissolve, and the reaction system was cooled in an ice-salt bath. A deionized aqueous solution of sodium nitrite (242.2 mg of sodium nitrite in 1.5 mL of deionized water, 3.5 mmol.) Was added dropwise to the system. The solution turned red. The reaction was stirred at 0 C for 30 minutes. After adding 3.0 mL of ether, a deionized aqueous solution of potassium iodide (2.0 g of potassium iodide in 1.5 mL of deionized water, 12 mmol.) Was added dropwise, and stirred for 3 hours. After the reaction was completed, a saturated sodium thiosulfate solution was added and extracted three times with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product.The crude product was subjected to petroleum ether column chromatography to obtain 518 mg of a relatively pure white 4-iodo-2,3-dihydrobenzofuran solid product in a yield of 70%.

As the paragraph descriping shows that 61090-37-7 is playing an increasingly important role.

Reference£º
Patent; Wuhan University; Zhou Qianghui; Gao Shijun; Qian Guangyin; (10 pag.)CN110483456; (2019); 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.62119-70-4,2-Benzofuranacetic acid,as a common compound, the synthetic route is as follows.

Example 49 Synthesis of N-[(benzofuran-2-yl)acetyl]alanine iso-butyl ester Following General Procedure I above, and using benzofuran-2-ylacetic acid (Maybridge) and alanine iso-butyl ester (prepared following General Procedure J above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): delta = 7.51 (m, 1H), 7.44 (m, 1H), 7.25 (m, 2H), 6.67 (s, 1H), 4.60 (m, 1H), 3.87 (m, 2H), 3.77 (s, 2H), 1.88 (m, 1H), 1.38 (d, 3H), 0.87 (d, 6H). C17H21NO4 (MW = 303, Mass Spectroscopy (MH+ 304)). GENERAL PROCEDURE IP-EPC coupling P-EPC coupling employs an amino acid ester and a substituted acetic acid compound. The acetic acid derivative is well known in the art and is typically commercially available. The amino acid ester is prepared by conventional methods from the known and typically commercially available N-BOC amino acid as described in GENERAL PROCEDURE J below. Specifically, the appropriate amino ester free base (0.0346 mmols) and substituted phenylacetic acid (0.069 mmols) were dissolved in 2.0 mL CHCl3 (EtOH free), treated with 150 mg of P-EPC (0.87 meq./g) and the reaction was mixed for 4 days at 23C. The reaction was filtered through a plug of cotton, rinsed with 2.0 mL of CHCl3 and the filtrate evaporated under a stream of nitrogen. The purity of each sample was determined by 1H NMR and ranged from 50% to >95%. Between 8.0 and 15.0 mg of final product was obtained from each reaction and was tested without additional purification

As the paragraph descriping shows that 62119-70-4 is playing an increasingly important role.

Reference£º
Patent; Elan Pharmaceuticals, Inc.; ELI LILLY AND COMPANY; EP951464; (2005); B1;,
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Benzofuran | C8H6O – PubChem

10242-08-7, 5-Methoxybenzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 7 2-(5-methoxybenzofuran-2-yl)imidazole hydrochloride R1 =H R2 =5-methoxy This was prepared from 5-methoxybenzofuran-2-carboxylic acid according to the methods a-e as described in example 1; m.p.=232-235 C. 1 H-NMR (DMSO-d6): 3.80 (s,3H), 7.10 (dd,1H), 7.40 (d,1H), 7.65 (d,1H), 7.80 (s,2H), 8.10 (s,1H). 13 C-NMR (DMSO-d6): 56.0, 104.7, 110.3, 112.7, 116.9, 121.2, 128.3, 135.6, 141.8, 150.0, 157.0.

10242-08-7 5-Methoxybenzofuran-2-carboxylic acid 288638, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S); US5310930; (1994); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

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: n-Butyllithium (1.67 M solution in hexane, 2.9 mL, 4.8 mmol) was added dropwise into a solution of 1,3-dimethoxybenzene (0.55 g, 4.0 mmol) in THF (5 mL) at 0 C and the mixture was stirred for 2 h at the same temperature. Then, DMF (0.34 mL, 4.4 mmol) was added to the mixture and the obtained mixture was stirred at 0 C. After 2 h at the same temperature, aq NH3 (8 mL, 120 mmol) and I2 (1.12 g, 4.4 mmol) were added and stirred for 2 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (15 mL) and was extracted with Et2O (3¡Á20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide 2,6-dimethoxybenzonitrile in over 80% purity. The product was purified by a short column chromatography on silica gel (Hexane/EtOAc=3:1) to give pure 2,6-dimethoxybenzonitrile in 91% yield as a colorless solid.

271-89-6 Benzofuran 9223, abenzofuran compound, is more and more widely used in various.

Reference£º
Article; Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 67; 5; (2011); p. 958 – 964;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.652-39-1,4-Fluoroisobenzofuran-1,3-dione,as a common compound, the synthetic route is as follows.

To methanol (175 mL) was added sodium hydride (3.36g, 60percent dispersion, 84.0 mmol) portionwise at ambient temperature under nitrogen. To the solution was added a solution of 3-fluorophthalic anhydride (5.56g, 33.5 mmol) in methanol (50 mL) dropwise under nitrogen at room temperature. The reaction was then worked-up as described for Example 56A to afford the title compound. The NMR data showed the product to be contaminated with 20percent of the 6-fluoro isomer. The material was used without further purification in the next step. 1H NMR (300 MHz, DMSO-J6) delta ppm 3.79 – 3.84 (two s, 3 H) 7.53 – 7.69 (m, 2 H) 7.76 (ddd, /=15.60, 7.29, 1.53 Hz, 1 H) 13.56 (s, 1 H); MS (+DCIZNH3) m/z 216.0 [M+NH4]+.

652-39-1 4-Fluoroisobenzofuran-1,3-dione 69551, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; ABBOTT LABORATORIES; AKRITOPOULOU-ZANZE, Irini; BRAJE, Wilfried; DJURIC, Stevan, W.; WILSON, Noel, S.; TURNER, Sean, C.; KRUGER, Albert, W.; RELO, Ana-Lucia; SHEKHAR, Shashank; WELCH, Dennie, S.; ZHAO, Hongyu; GANDARILLA, Jorge; GASIECKI, Alan, F.; LI, Huanqiu; THOMPSON, Christina, M.; ZHANG, Min; WO2010/135560; (2010); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-41-3, Benzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Oxalyl chloride (3.13 mL, 3.70 mmol) was added to a suspension of benzofuran-2- carboxylic acid (5.00 g, 3.08 mmol) in DCM (100 mL, anhydrous) and DMF (0.1 mL, 1.3 mmol) at r.t.. The mixture was stirred at r.t. for 1 h to give a colourless solution which was cooled to 0 C. N,O-Dimethylhydroxylamine hydrochloride (3.31 g, 3.39 mmol) and pyridine (7.5 mL, 9.27 mmol) were added sequentially and the mixture was stirred at r.t. for 18 h, then partitioned between EtOAc and sat. aq. NaHC03. Column chromatography (3 : 1 hexanes:EtOAc) gave 121 (6.32 g, 100%). 1H MR (CDC13) delta 7.69 (ddd, 7.9, 1.2, 0.7 Hz, 1H), 7.61 (ddd, J = 8.4, 1.7, 0.9 Hz, 1H), 7.51 (d, J = 1.0 Hz, 1H), 7.48 (ddd, J = 7.9, 7.2, 1.3 Hz, 1H), 7.30 (ddd, J = 7.5, 7.3, 0.9 Hz, 1H), 3.84 (s, 3H), 3.43 (s, 3H). Found: [M+H]=206.2. l-(Benzofuran-2-yl)-3-(dimethylamino ropan-l-one (122)

As the paragraph descriping shows that 496-41-3 is playing an increasingly important role.

Reference£º
Patent; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.; UPTON, Anna, Marie; COOPER, Christopher, Blair; MARCEL, Koenraad, Jozel Lodewijk; GUILLEMONT, Jerome, Emile Goerges; VAN DEN BROECK, Walter Marcel, Mathilde; PALMER, Brian, Desmond; MA, Zhenkun; (186 pag.)WO2017/155909; (2017); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-41-3, Benzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: In a 20 or 40 mL reaction vial equipped with magnetic stir bar and Teflon-lined cap, a solution of the corresponding carboxylic acid (1.5 mmol, 3.0 eq) and DMAP (183.3 mg, 1.5 mmol, 3.0 eq) in anhydrous DMF (9.0 mL) was homogenized by stirring for 5-10min. EDCI¡¤HCl (287.6mg, 1.5mmol, 3.0 eq) was added, and the resulting mixture was homogenized by stirring for 5-10 min. The corresponding 1,3-indandione (0.5mmol, 1.0 eq) was added, and the resulting mixture was resealed and stirred for 12-72h, monitoring by LCMS. When complete, workup method A, B, or C was used to isolate the final products.

496-41-3 Benzofuran-2-carboxylic acid 10331, abenzofuran compound, is more and more widely used in various.

Reference£º
Article; Larsen, Brian J.; Rosano, Robert J.; Ford-Hutchinson, Thomas A.; Reitz, Allen B.; Wrobel, Jay E.; Tetrahedron; vol. 74; 22; (2018); p. 2762 – 2768;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

641-70-3, 3-Nitrophthalic anhydride is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A round bottom flask was charged with a solution of glacial acetic acid (75 ml) and alpha-amino glutarimide hydrochloride (8.5 g). Sodium acetate anhydrous (4.5 g) was added lot-wise to the solution at 25 C. to 30 C. followed by addition of 3-nitro phthalic anhydride (log) at the same temperature. The reaction mixture was stirred at 118 C. for 18 hr. After the completion of reaction, the reaction mass was cooled to 60 C. and the solvent was distilled off under vacuum to get the residue. To the residue obtained, water (100 ml) was added; the mixture was stirred for 1 hr at 25 C. to 30 C. and the mass filtered. The wet cake obtained was slurried with water (100 ml*2), filtered and dried in an air tray dryer until the water content was less than 0.5% to afford 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione (14 g). Yield: 89.7%, Purity: 98%.

As the paragraph descriping shows that 641-70-3 is playing an increasingly important role.

Reference£º
Patent; Apicore US LLC; Kovi, Ravishanker; Bobbili, Veerabhadra Rao; Kannapan, Jayaraman; (13 pag.)US2017/260157; (2017); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem