Heterocyclic Building Block-benzofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.69604-00-8,Ethyl 5-nitrobenzofuran-2-carboxylate,as a common compound, the synthetic route is as follows.,69604-00-8

Ethyl 5-nitro-1-benzofuran-2-carboxylate (2.0 g, 8.54 mmol) was suspended in a mixed solvent of methanol (3.2 mL) and THF (3.2 mL), then a 4 mol/L aqueous solution of sodium hydroxide (3.2 mL) was added thereto, and the mixture was stirred at 70C for 1 hour. A 1 mol/L aqueous solution of hydrochloric acid was added to the reaction solution, followed by extraction with ethyl acetate twice. The organic layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate and filtered, and then the solvent was concentrated under reduced pressure to obtain a crude product. The obtained crude product was dissolved in DMF (20 mL), then 1,1-di-tert-butoxy-N,N-dimethylmethaneamide (13.9 g, 68.32 mmol) was added, and the mixture was stirred at 80C for 11 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate and filtered, and then the organic layer was concentrated under reduced pressure to obtain a crude product. Chloroform (10 mL) was added to the obtained crude product, and the crystal was filtered out to obtain the title compound (1.76 g, 78%). 1H NMR (CDCl3, 300 MHz) delta 12.43 (s, 1H), 8.13-8.11 (m, 1H), 7.61-7.59 (m, 1H), 7.34 (s, 1H), 2.11-1.98 (m, 4H), 1.64-1.59 (m, 9H).

As the paragraph descriping shows that 69604-00-8 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Dainippon Pharma Co., Ltd.; IKUMA Yohei; FUKUDA Nobuhisa; IWATA Masato; KIMURA Hidenori; SUZUKI Kuniko; EP2876105; (2015); 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.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.,69999-16-2

Step 3. N-[2-(2, 3-dihydro-l-benzofiiotaran-5~ylmethyl)-l-(3-methylbutyl)-lH-benzimidazol-5-yl]~ N, 3-dimethylbutanamide[0171] To a mixture of N-{3-amino-4-[(3-methylbutyl)amino]phenyl}-N,3-dimethylbutanamide (Step 2 of Example 2, 0.097g, 0.33 mmol, lequiv), 2,3-dihydro-l-benzofuran-5-ylacetic acid (0.065g, 0.36 mmol, 1.1 equiv) and HATU (0.139g, 0.366 mmol, 1.1 equiv) was added a solution of DIPEA (116 muL, 0.666 mmol, 2equiv) in DMF (5 mL). The mixture was stirred overnight at room temperature. Complete consumption of the starting material was confirmed by LC-MS. DMF was removed under reduced pressure. Ethyl acetate was added to the resulting residue. The organic layer was washed once with a saturated aqueous NaHCO3 solution, once with brine and dried over anhydrous Na2SO4. Ethyl acetate was removed under reduce pressure. The resulting residue was dissolved in dichloroethane and a few drops of concentrated HCl were added. The mixture was stirred at 80 C for a few hours. Complete consumption of the starting material was confirmed by LC-MS. Dichloromethane was added. The organic layer was washed once with a 2M aqueous NaOH solution, once with brine and dried over anhydrous Na2SO4. Dichloromethane was removed under reduced pressure. The resulting residue was purified by reversed-phase HPLC and lyophilized to afford N-[2-(2,3-dihydro-l-benzofuran-5-yhnethyl)-l- (3-methylbutyl)-lH-benzimidazol-5-yl]-N,3-dimethylbutanamide as the corresponding TFA salt (0.110 mg) in 58% yield. 1H NMR (400 MHz, METHANOL-D4) delta ppm 0.72 – 0.89 (m, 6 H) 0.96 (d, /=6.64 Hz, 6 H) 1.47 – 1.54 (m, 2 H) 1.64 – 1.76 (m, 1 H) 1.91 – 2.14 (m, 3 H) 3.19 (t, /=8.69 Hz, 2 H) 4.36 – 4.43 (m, 2 H) 4.50 (s, 2 H) 4.55 (t, /=8.69 Hz, 2 H) 6.76 (d, /=8.20 Hz, 1 H) 7.08 (dd, /=8.30, 1.86 Hz, 1 H) 7.21 (s, 1 H) 7.46 (dd, /=8.79, 1.95 Hz, 1 H) 7.65 (d, /=1.37 Hz, 1 H) 7.85 (d, /=8.59 Hz, 1 H); MS (ESI) m/z 434.0 (M+H)+; Anal. Calcd (%) for C27H35N3O2 + 1.1 TFA + 0.1 H2O: C, 62.54; H3 6.52; N, 7.49. Found: C, 62.51; H, 6.59; N 7.46.

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; WO2007/91950; (2007); 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.700-85-6,5-Fluoroisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.,700-85-6

250ml single-mouth bottle to join5-F-benzofuran-1 (3H) ketone 2g, absolute ethanol 120ml, dropping thionyl chloride 4.8ml, drop complete, reflux 14h, vacuum evaporated.

As the paragraph descriping shows that 700-85-6 is playing an increasingly important role.

Reference£º
Patent; Chongqing Institute of Pharmaceutical Industry Co., Ltd.; Dan, Chunyan; Cai, Pengfei; Zuo, Xiaoyong; Luo, Bin; Xie, Shouquan; Liu, Caiping; Yang, Qiaobin; (8 pag.)CN105524044; (2016); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

7168-85-6, 7-Methoxybenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7168-85-6

Preparation 13 Benzofuran-7-ol To 7-methoxy benzofuran (6.3 g, 42.5 mmol) in a 0.5 M solution of CH2Cl2 at -78 C. is added tetrabutylammonium iodide (18.9 g, 51 mmol). To this stirred solution, BCl3 (100 mL of a 1.0 M solution in CH2Cl2, 100 mmol) was added dropwise via addition funnel. The reaction mixture was stirred at -78 C. for 6 h. Water is added dropwise very slowly to quench. The resulting mixture was stirred overnight at rt, basified with 6 N NaOH (pH=10), stirred for 1 h, neutralized with 2 N HCl (pH=7), and extracted with CH2Cl2 (5*). The combined extracts were dried (MgSO4), filtered, concentrated, and chromatographed (10% EtOAc in hexanes) to provide 5.3 grams of benzofuran-7-ol as an oil. 1H NMR (400 MHz, CDCl3): delta 7.61 (d, 1, J=2.1), 7.19 (d, 1, J=7.7), 7.13 (t, 1, J=7.7), 6.88 (d, 1, J=7.7), 6.79 (d, 1, J=2.1), 6.04 (bs, 1). Previously prepared but no data reported: Musser, J. H.; Chakraborty, U.; Bailey, K.; Sciortino, S.; Whyzmuzis, C.; Amin, D.; Sutherland, C. A. J. Med. Chem. 1987, 30, 62-67.

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

Reference£º
Patent; Pfizer Inc; US2006/58361; (2006); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

763114-25-6, 2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,763114-25-6

(b) 2-Fluoro-5-[(4-oxo-3, 4-dihydrophthalazin-1-yl)methyl]benzonitrile (ED) 2-Fluoro-5-[(E/Z)-(3-oxo-2-benzofuran-1 (3/-/)-ylidene)methyl]benzonitrile (E)(20g, 75.40 mmol) and tetrahydrofuran (200 ml) were stirred at room temperature under a nitrogen atmosphere for 30 minutes. Hydrazine monohydrate (4.40 ml, 90.53 mmol) was added, followed by a line wash of tetrahydrofuran (4 ml). The reaction mixture was stirred at room temperature for 1 hour 45 minutes. Acetic acid (1.10 ml, 19.20 mmol) was added and the reaction mixture warmed to 600C. The reaction mixture was held at 600C overnight. The reaction mixture was cooled to 50¡ãC and water (200 ml) added dropwise. The temperature was maintained at 45¡ãC throughout the addition. The reaction mixture was cooled to 200C1 filtered, washed with a mixture of water (30 ml) and tetrahydrofuran (30 ml), and then dried in vacuo at up to 4O0C to give the title compound (18.7 g).Mass spectrum: MH+ 2801 H NMR (400MHz. DMSO-d6) delta: 4.38 (s, 2H), 7.46 (t, 1 H), 7.72 (m, 1 H), 7.85 (dt, 1 H), 7.92 (m, 2H), 7.99 (d, 1 H), 8.27 (dd, 1 H), 12.57 (s, 1 H).

As the paragraph descriping shows that 763114-25-6 is playing an increasingly important role.

Reference£º
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2008/47082; (2008); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.84594-78-5,6-Nitro-2,3-dihydrobenzofuran-5-amine,as a common compound, the synthetic route is as follows.,84594-78-5

A suspension of 6-nitro-2,3-dihydrobenzofuran-5-amine [CAS 84594-78-5] (135.00g, 749.33 mmol) in concentrated HCI (250 mL) was heated to 100C for 10 mm.The solution was cooled to 0C. A solution of NaNO2 (62.04 g, 899.20 mmol) inH20 (250 mL) was added dropwise. The reaction mixture was stirred for 30 mm at0C. The reaction mixture was added slowly to a cooled (0C) solution of KI(186.58 g, 1.12 mol) in H20 (250 mL). The resulting mixture was heated to 70C for 2 h. After cooling to room temperature, H20 (2 L) was added and the crude product was extracted with EtOAc (2x 2 L). The combined organic phases were washed with aqueous HCI (10%, 1 L), aqueous NaOH (1 N, 1 L), a saturated aqueous Na2SO3 solution (1 L) and brine (1 L). After drying over MgSO4, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: petroleum ether/EtOAc 8/1) to give5-iodo-6-nitro-2,3-dihydrobenzofuran 7a (90.00 g) as a pale yellow solid.

As the paragraph descriping shows that 84594-78-5 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; COESEMANS, Erwin; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (96 pag.)WO2017/167952; (2017); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

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,90843-31-5

General procedure: The target thiosemicarbazones were prepared by dissolving corresponding ketone (2a-b) (0.005 mol) and appropriate thiosemicarbazide (1a-q) (0.005 mol) in ethanol containing 1-2 drops of HCl as catalyst. The reaction mixture was heated under reflux at 80 C for 2-3 h and course of the reaction was monitored by TLC. After the reaction completion,the excess solvent was evaporated under vacuum and the crystalline or amorphous product formed was filtered, washed with hot ethanol and then with diethyl ether to afford the required thiosemicarbazones (3a-u) in excellent yields. The synthesized thiosemicarbazones were further recrystallized by mixture of chloroform-ethanol (1:1). For X-ray measurements, single crystal of 3m was mounted on a MiTeGen loop with grease and examined on a Bruker D8 Venture APEX diffractometer equipped with Photon 100 CCD area detector and Oxford Cryostream cooler at 296 (2) K using graphite-monochromated Mo-Kalpharadiation (lambda=0.71073 A). Data was collected using the APEX-II software [33], integrated using SAINT [34] and corrected for absorption using a multi-scan approach (SADABS) [35]. The structure was solved using intrinsic phasing (SHELXT) [36]. Final cell constants were determined from full least squares refinement of all observed reflections. All non-H atoms were located in subsequent difference maps and refined anisotropically with SHELXL-97 [37], using full least squares refinement against F2. H-atoms were added at calculated positions and refined with a riding model. The structure has been deposited with the CCDC (CSD deposition numbers 1874544).

As the paragraph descriping shows that 90843-31-5 is playing an increasingly important role.

Reference£º
Article; Islam, Muhammad; Khan, Ajmal; Shehzad, Muhammad Tariq; Hameed, Abdul; Ahmed, Nadeem; Halim, Sobia Ahsan; Khiat, Mohammed; Anwar, Muhammad Usman; Hussain, Javid; Csuk, Rene; Shafiq, Zahid; Al-Harrasi, Ahmed; Bioorganic Chemistry; vol. 87; (2019); p. 155 – 162;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10242-12-3,5-Nitrobenzofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.,10242-12-3

(d). 5-Nitrobenzofuran. To a 100 mL round-bottomed flask was added 5-nitrobenzo[b]furan-2-carboxylic acid, Example 38(c), (860 mg, 4.2 mmol), copper (830 mg, 13 mmol, Aldrich), and quinoline (38 mL, Aldrich). The reaction flask was placed in a 185 C. oil bath and magnetically stirred for 20 min under N2. After allowing to cool to 25 C., the mixture was filtered through a 1″ pad of Celite. To the filtrate was added 10% aq. HCl (300 mL) and the aqueous layer was extracted with Et2O (3*100 mL). The combined ethereal layers were washed with 10% HCl (4*200 mL, 1*100 mL), satd NaHCO3 (200 mL), and satd NaCl (100 mL), dried over MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (10:0.25 hexanes:EtOAc) provided 5-nitrobenzofuran as a white solid.

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

Reference£º
Patent; Bo, Yunxin Y.; Chakrabarti, Partha P.; Chen, Ning; Doherty, Elizabeth M.; Fotsch, Christopher H.; Han, Nianhe; Kelly, Michael G.; Liu, Qingyian; Norman, Mark Henry; Ognyanov, Vassil I.; Wang, Xianghong; Zhu, Jiawang; US2003/195201; (2003); 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.127264-14-6,5-(2-Bromoethyl)-2,3-dihydrobenzofuran,as a common compound, the synthetic route is as follows.,127264-14-6

The compound (3S) -pyrrolidin-3-yl cyclopentyl (hydroxy) phenylacetate (0.2 g, 0.69 MM) was dissolved in acetonitrile (5.0 ml) followed by the addition of 5- (2-bromoethyl)-2, 3- DIHYDRO-1-BENZOFURAN (0.173 g, 0.76 mM), potassium carbonate (0.29 g, 2.01 MM) and potassium iodide (0.23 g, 1.38 mM). The reaction mixture was heated under reflux for 8 hours and then cooled to room temperature. Acetonitrile was evaporated under vacuum. The residue was partitioned between ethyl acetate (30.0 ml) and water (30.0 ml). The organic layer was washed with water and brine solution followed by drying over anhydrous sodium sulphate. The residue was purified by silica get column chromatography using 10percent methanol in chloroform to get the title compound as oil. Yield = 50percent (0. 15 G, 0. 34 MM). 1H NMR (CDCl3) : delta 7.66 (d, J = 7 Hz, 2H), 7.31-7.36 (M, 3H), 7.03 (d, J = 8 Hz, 1H), 6.93 (t, J = 8 Hz, 1H), 6.69-6.72 (M, 1H), 5.22-5.24 (M, 1H), 4.55 (t, J = 9 Hz, 2H), 3.76 (br M, 1H), 3.18 (t, J = 9 Hz, 2H), 2.54-2.92 (M, 8H), 2.00-2.50 (M, 1H), 1.25-1.63 (M, 1 OH, including-OH).

The synthetic route of 127264-14-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; RANBAXY LABORATORIES LIMITED; WO2004/56767; (2004); 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.133720-60-2,7-Bromobenzofuran,as a common compound, the synthetic route is as follows.,133720-60-2

EXAMPLE 43 cis -3-methyl-4-(benzofur-7-yl)piperidine hydrochloride Beginning with 7 gm (35.5 mMol) 7-bromobenzofuran and 7.9 gm (39 mMol) 1-benzyl-3-methyl-4-oxopiperidine, 1.92 gm (21%) of the title compound were prepared as a white powder essentially as described in EXAMPLE 19. EA: Calculated for C14H17NO-HCl: C, 66.79; H, 7.21; N, 5.56. Found: C, 66.41; H, 7.02; N, 5.70.

The synthetic route of 133720-60-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; EP1204659; (2003); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem